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Under reducing conditions, the thermal stability of the wild-type was decreased to a level nearly equivalent to that of a Cys-free mutant C4S⁄ C18S ⁄ C29S ⁄ C60S in which all Cys residue

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Shunsuke Kawamura1, Mari Ohkuma1, Yuki Chijiiwa1, Daiki Kohno1, Hiroyuki Nakagawa1, Hideki Hirakawa2, Satoru Kuhara2,3and Takao Torikata1

1 Department of Bioscience, School of Agriculture, Tokai University, Aso, Kumamoto, Japan

2 Graduate School of Systems Life Sciences, Kyushu University, Hakozaki, Higashi-ku, Fukuoka, Japan

3 Graduate School of Genetic Resource Technology, Kyushu University, Hakozaki, Higashi-ku, Fukuoka, Japan

Lysozyme, one of the best characterized

carbohydro-lases, cleaves the glycosidic linkage between

N-acetyl-glucosamine (GlcNAc) and N-acetylmuramic acid in

bacterial cell walls This enzyme is classified into

six types, chicken type (C-type) [1–3], phage type

(T4-type) [4,5], goose type (G-type) [6–8], invertebrate

type [9–11], bacteria type [12], and plant type [13], on

the basis of the similarity in amino acid sequences

These different classes of lysozymes have overall

simi-larities in tertiary structure [7,14–17], although their

amino acid sequences are almost entirely different

Much information on the structural properties and enzymatic mechanisms of C-type and T4-type lyso-zymes has been accumulated thus far In particular, hen egg-white lysozyme and human lysozyme, which belong to a class of C-type lysozymes with four disul-fide bonds, and T4 phage lysozyme with no disuldisul-fide bonds, have been intensively studied as model proteins for elucidating enzymatic function and protein stabil-ity In contrast to C-type and T4-type lysozymes, information on G-type lysozyme is limited In verte-brates, the primary structure has been reported for five

Keywords

disulfide bonds; goose-type lysozyme;

ostrich; site-directed mutagenesis; structural

stability

Correspondence

S Kawamura, Department of Bioscience,

School of Agriculture, Tokai University, Aso,

Kumamoto 869-1404, Japan

Fax: +81 967 67 3960

Tel: +81 967 67 3918

E-mail: kawamura@agri.u-tokai.ac.jp

(Received 15 November 2007, revised 3

March 2008, accepted 25 March 2008)

doi:10.1111/j.1742-4658.2008.06422.x

The role of the two disulfide bonds (Cys4–Cys60 and Cys18–Cys29) in the activity and stability of goose-type (G-type) lysozyme was investigated using ostrich egg-white lysozyme as a model Each of the two disulfide bonds was deleted separately or simultaneously by substituting both Cys residues with either Ser or Ala No remarkable differences in secondary structure or catalytic activity were observed between the wild-type and mutant proteins However, thermal and guanidine hydrochloride unfolding experiments revealed that the stabilities of mutants lacking one or both of the disulfide bonds were significantly decreased relative to those of the wild-type The destabilization energies of mutant proteins agreed well with those predicted from entropic effects in the denatured state The effects of deleting each disulfide bond on protein stability were found to be approxi-mately additive, indicating that the individual disulfide bonds contribute to the stability of G-type lysozyme in an independent manner Under reducing conditions, the thermal stability of the wild-type was decreased to a level nearly equivalent to that of a Cys-free mutant (C4S⁄ C18S ⁄ C29S ⁄ C60S) in which all Cys residues were replaced by Ser Moreover, the optimum tem-perature of the catalytic activity for the Cys-free mutant was downshifted

by about 20C as compared with that of the wild-type These results indi-cate that the formation of the two disulfide bonds is not essential for the correct folding into the catalytically active conformation, but is crucial for the structural stability of G-type lysozyme

Abbreviations

(GlcNAc)n, b-1,4-linked oligosaccharide of GlcNAc with a polymerization degree of n; C-type, chicken type; GEL, goose egg-white lysozyme; GlcNAc, N-acetylglucosamine; G-type, goose type; MD, molecular dynamics; OEL, ostrich egg-white lysozyme; T4-type, phage type; b-ME, b-mercaptoethanol.

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G-type lysozymes, i.e those from ostrich [18], black

swan [19], embden goose [6], cassowary [20], and rhea

[21], and five from chicken [22], flounder [23], carp

[24], salmon [25], and orange-spotted grouper [26]

Additionally, Irwin & Gong [27] reported that

mam-mals and zebrafish carry two G-type lysozyme genes

Recently, invertebrate G-type lysozyme genes and⁄ or

enzyme activity from scallop [28,29] and tunicate [30]

were also reported G-type lysozyme differs from the

C-type in that it is much more specific for

peptide-substituted substrate [31] C-type lysozyme hydrolyzes

a homopolymer (chitin) effectively, whereas G-type

lysozyme is a poor catalyst of the hydrolysis of this

substrate The differences in substrate specificity

between these lysozymes and the mechanistic details of

the catalytic reaction of G-type lysozyme remain

unclear Previously, Honda & Fukamizo reported the

mode of binding of GlcNAc oligomer to goose

egg-white lysozyme (GEL), and postulated that GEL has

six substrate-binding subsites (sites B–G) [32] This

subsite structure was partly visualized in terms of the

crystal structure of the GEL–(GlcNAc)3 complex [14];

however, part of the subsite structure (sites E–G)

remains unknown

On the basis of sequence comparison of G-type

lyso-zymes, we have shown that the amino acid sequences

of three a-helices (a5, a7, and a8) are highly conserved

in this enzyme group [20,21] These three a-helices are

located at the center of the protein molecule, and form

a hydrophobic core in the overall structure of G-type

lysozyme (Fig 1) Recently, using ostrich egg-white

lysozyme (OEL) as a model, we demonstrated the

involvement of Glu73 on a5 (Ala64–Glu73) as a

criti-cal catalytic residue and also indicated the crucial role

of Glu73 in the structural stability of G-type lysozyme,

probably through the interhelical hydrogen bond with Tyr169 on a8 (Tyr169–Gln182) [33] These observa-tions suggest that the core elements (a5, a7, and a8) play an important role in the maintenance of the three-dimensional structure of G-type lysozyme

In addition to the three a-helices, the Cys4–Cys60 and Cys18–Cys29 disulfide bonds (numbering from bird sequences), which are located in the N-terminal region, are completely conserved in avian and mamma-lian G-type lysozymes, although another three Cys res-idues are conserved from mouse to human [20,21,27]

In the crystal structure of GEL (Fig 1), which shares 83% amino acid identity with OEL, these two disulfide bonds are located on the molecular surface, although Cys60 is partially buried in the interior of the protein

It has been shown that the integrity of the native three-dimensional structure of many proteins is pro-moted by the presence of disulfide bonds, because removal of one or more of these linkages results in a reduction in the stability of the native state relative to the denatured state [34–44] On the other hand, none

of the four disulfide bonds was reported to be impor-tant in stabilizing the native structure of the Pseudoal-teromonas haloplanktis a-amylase [45] It was also shown that the Cys191–Cys220 disulfide bond, which

is highly conserved in the trypsin family of serine pro-teases, is not essential for the catalytic function, struc-ture and stability of trypsin [46] Therefore, analysis of the role of the disulfide bonds in activity and stability will be useful for our understanding of the structure– function relationship of G-type lysozyme The present article describes a site-directed mutational analysis of OEL to address the role of the disulfide bonds in G-type lysozyme

Results and Discussion Choice of residues for mutagenesis

A striking difference within G-type lysozymes is the variation in Cys content There are four conserved Cys residues in avian and mammalian G-type lysozymes, which form two intramolecular disulfide bonds in the mature proteins [20,21,27] The crystal structure of GEL shows that the Cys18–Cys29 disulfide bond con-nects the N-terminus of a-helix 1 with a loop between a-helices 1 and 2, and the Cys4–Cys60 disulfide bond connects the N-terminal long loop with a loop between a-helices 4 and 5 The G-type lysozymes found in fish have either no Cys residue, as in flounder and grouper [23,26], one, as in carp and salmon [24,25], or two (no potential to form an intramolecular disulfide bond),

as in zebrafish [27] The absence of intramolecular

Fig 1 The three-dimensional structure of GEL The structure was

created using the coordinate file, Protein Data Bank entry 153L

[14] The two disulfide bonds (Cys4–Cys60 and Cys18–Cys29) and

three a-helices (a5, a7, and a8) are shown in blue and green,

respectively The side chain of Glu73 is also shown in red The

figure was generated using MOLSCRIPT (v 2.1.2).

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disulfide bonds seems to be a common characteristic

among the fish G-type lysozymes The G-type

lyso-zymes in invertebrates have six to 13 Cys residues

other than the four Cys residues conserved in avian

and mammalian G-type lysozymes, which renders the

disulfide patterns of invertebrate G-type lysozymes

quite different from those of the bird and mammalian

lysozymes [28–30] As the locations of disulfide bonds

in invertebrate G-type lysozymes have not yet been

identified, we decided to focus our attention on the

Cys18–Cys29 and Cys4–Cys60 disulfide bonds, which

are absolutely conserved in avian and mammalian

G-type lysozymes

Expression and characterization of mutant

proteins

To investigate the contribution of the two disulfide

bonds to the activity and stability of G-type lysozyme,

three mutant proteins (C4S⁄ C60S, C18S ⁄ C29S, and

C4S⁄ C18S ⁄ C29S ⁄ C60S), in which each of the disulfide

bonds was singly or together disrupted by Cysfi Ser

mutations, were initially constructed The Ser residue

was chosen because it is structurally similar to Cys

except that it contains a hydroxyl group instead of a

thiol group The mutant proteins were expressed and

purified in the same manner as used for the wild-type

[33] The yields of the mutant proteins were

com-parable to that of the wild-type, approximately

60–70 mgÆL)1 The purified proteins were found to be

homogeneous on analysis by SDS⁄ PAGE, and gave a

single peak on RP-HPLC (data not shown) The

N-ter-minal sequence of each mutant protein was determined

to be Ser-Arg-Thr-Gly, which coincided with that of

the wild-type, indicating that each mutant was correctly

processed at the C-terminus of the a-factor signal The

integrity of the mutant proteins was confirmed by

mea-surements of far-ultraviolet CD The CD spectra of the

three mutants were almost indistinguishable from that

of the wild-type (Fig 2), indicating that the backbone

conformation of the mutant proteins is practically the

same as that of the wild-type Thus, it appears that

none of the disulfide bonds are critically important to

the folding process of G-type lysozyme

Effects of mutations on catalytic activity

We previously reported that the recombinant OEL

preferentially hydrolyzes the third glycosidic linkage

from the nonreducing end of (GlcNAc)6, and the

cleavage pattern seen for (GlcNAc)5 is similar to that

seen for (GlcNAc)6 [47] To examine the effects of the

mutations on the catalytic activity of G-type lysozyme,

we initially analyzed the activities of the wild-type and its mutants by monitoring the enzyme-catalyzed lysis

of Micrococcus luteus cells, which is a high molecular mass polymeric substrate with a highly negative charge Mutant C4S⁄ C60S had lytic activity to the same extent as the wild-type, exhibiting 99.0% activity The lytic activities of mutants C18S⁄ C29S and C4S⁄ C18S ⁄ C29S ⁄ C60S were 76.5% and 70.6% of that

of the wild-type, respectively (data not shown) As the substrate used for lytic activity is chemically heteroge-neous, the activities of the wild-type and three mutant proteins were more precisely evaluated by measuring the enzyme-catalyzed hydrolysis of (GlcNAc)5 (Fig 3) Consistent with the results obtained in the M luteus assay, the wild-type and mutant C4S⁄ C60S hydrolyzed the initial substrate (GlcNAc)5 almost completely after

240 min of reaction, and (GlcNAc)5 was hydrolyzed mainly to (GlcNAc)2+ (GlcNAc)3 with much less cleavage to (GlcNAc)1+ (GlcNAc)4 Mutants C18S⁄ C29S and C4S ⁄ C18S ⁄ C29S ⁄ C60S hydrolyzed (GlcNAc)5 to produce (GlcNAc)2 and (GlcNAc)3, as

in the case of the wild-type, although the overall rates

of hydrolysis were slightly affected by each of the mutations: the two mutants took 420 min to hydrolyze most of the (GlcNAc)5 These results are consistent with the fact that each of the two disulfide bonds is

–30 –20 –10 0 10 20 30 40 50 60

190 210 230 250

Wavelength (nm)

3 (deg cm

2 ·dmol

Wild type C18S/C29S C4S/C60S C4S/C18S/C29S/C60S

Fig 2 CD spectra of the wild-type and its three mutant proteins in the far-UV region.

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far apart from the catalytic glutamate, Glu73, in the

crystal structure of GEL (even the nearest two

resi-dues, Cys18 and Glu73, are located 16.8 A˚ apart from

each other) Although the reason for the slight

reduc-tion in the activity of the two mutants is presently

obscure, none of the disulfide bonds is considered to

be critically important to the catalytic function of

G-type lysozyme This observation, together with the

result obtained by CD analysis, implies that G-type

lysozyme can fold and function in the absence of both

disulfide bonds This is consistent with the findings

that the flounder and salmon G-type lysozymes, which

have no disulfide bonds in their native forms, and the

scallop G-type lysozyme, which has six Cys residues

other than the well-conserved four Cys residues in

birds, possessed lytic activity against Micrococcus

lysodeikticus[23,25,29]

Effects of mutations on stability

Disulfide bonds have been suggested to play an

impor-tant role in maintaining structural integrity and protein

stabilization This conclusion has been supported by

characterization of mutants of various proteins in

which disulfide bonds have been either deleted or

mod-ified For example, Pace et al [34] reported that

dis-ruption of one and two disulfide bonds in

ribonuclease T1 caused decreases in conformational

stability by 3.4 and 7.2–9.3 kcalÆmol)1, respectively

Many other examples can be found in the reviews by

Wetzel [48] and Bets [49] It is widely accepted that the

stabilizing effect of a disulfide bond can be attributed

principally to the destabilization of the unfolded form

by the loss of conformational entropy imposed by the

crosslink [34,36,39,50–54] However, the mechanism of protein stabilization by disulfide bond formation is difficult to resolve, because the disulfide bond may influence the enthalpy and entropy of both the native and unfolded states of the protein [49]

The thermal unfolding of the wild-type protein has been investigated using CD and fluorescence spectros-copy, and led to the observation that the unfolding transition of the wild-type is well represented by a two-state mechanism at pH 5.0 in the presence of 0.5 m guanidine hydrochloride [33] Like the wild-type pro-tein, the three mutants (C18S⁄ C29S, C4S ⁄ C60S, and C4S⁄ C18S ⁄ C29S ⁄ C60S) reversibly unfolded in a single cooperative fashion under these conditions The ther-mal unfolding curves of the wild-type and three mutant proteins obtained with fluorescence measurements are shown in Fig 4A Replacing Cys18 and Cys29 or Cys4 and Cys60 with a pair of Ser residues had significant effects on the thermal unfolding of the mutant proteins The Tmvalues for mutants C18S⁄ C29S and C4S ⁄ C60S were decreased by 6.3C and 9.5 C, respectively, as compared to 60.6C for the wild-type (Table 1) The Cys mutations reduced the thermostability of the pro-teins by 3.11 and 4.29 kcalÆmol)1 for mutants C18S⁄ C29S and C4S ⁄ C60S, respectively, at 60.6 C The combination of these destabilizing mutations (C4S⁄ C18S ⁄ C29S ⁄ C60S) caused a further decrease in thermostability relative to the wild-type by 15.3C (DDG:)6.14 kcalÆmol)1) (Table 1)

The contribution of the disulfide bonds to the struc-tural stability of OEL was further assessed by means

of unfolding experiments with guanidine hydrochloride

as a denaturant Figure 4B shows the guanidine hydro-chloride-induced unfolding curves of the wild-type and

Fig 3 Time course plots of (GlcNAc)5

degradation by the wild-type and its three

mutant proteins The enzymatic reaction

was performed in 10 m M sodium acetate

buffer (pH 4.0) at 40 C Numerals in the

figures are the polymerization degrees of

the reaction product species Relative error

indicates the recovery of the observed value

at each reaction time calculated as

described in Experimental procedures The

solid lines were drawn by roughly following

the experimental data points.

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mutant proteins obtained with fluorescence

measure-ments The transitions of the three mutant proteins

were highly cooperative The unfolding transitions of

the mutant proteins occurred at lower concentrations

of guanidine hydrochloride than that of the wild-type:

the Cmvalues were reduced, as compared with that of the wild-type, by 0.47, 0.70 and 1.07 m for mutants C18S⁄ C29S, C4S ⁄ C60S, and C4S ⁄ C18S ⁄ C29S ⁄ C60S, respectively (Table 2) The DGH2O values of unfolding indicated that the three mutants, C18S⁄ C29S, C4S⁄ C60S, and C4S ⁄ C18S ⁄ C29S ⁄ C60S, were destabi-lized by 2.33, 3.33 and 4.86 kcalÆmol)1, respectively, at

0 m guanidine hydrochloride in comparison to the wild-type

The decrease in the stability of the least stable C4S⁄ C18S ⁄ C29S ⁄ C60S mutant was further confirmed

by CD measurements: its thermal and guanidine hydrochloride transition curves derived from the CD and fluorescence data completely coincided, and the

Tm and Cm values obtained with CD were in good agreement with the data determined with fluorescence (Fig 5, and Tables 1 and 2) The coinciding transitions derived from these two different methods also indicate that the Cys-free mutant undergoes thermal and guani-dine hydrochloride-induced denaturation, which is con-sidered to be a reversible two-state process as observed

in the wild-type It is thus likely that the fold-ing⁄ unfolding pathway of G-type lysozyme does not significantly change in the absence of one or both of the disulfide bonds, which supports the notion that the presence of a complete set of disulfide bonds is not required for the folding process of G-type lysozyme

To corroborate the importance of the disulfide bonds in the structural stability of OEL, two mutant proteins (C18A⁄ C29A and C4A ⁄ C60A), in which Cys18 and Cys29 or Cys4 and Cys60 were replaced

by Ala, respectively, were constructed and analyzed with respect to their guanidine hydrochloride dena-turation (Fig 4B and Table 2) It was found that mutants C18A⁄ C29A and C4A ⁄ C60A exhibited the same stabilities as mutants C18S⁄ C29S and C4S⁄ C60S, respectively, which strongly suggests that the observed destabilization arising from the Cys to Ser or Ala mutations is not due to negative side

–0.2

0

0.2

0.4

0.6

0.8

1.0

1.2

Temperature (ºC)

Wild-type C18S/C29S C4S/C60S C4S/C18S/C29S/C60S Wild-type (reduced)

–0.2

0

0.2

0.4

0.6

0.8

1.0

1.2

GdnHCl ( M )

Wild-type C18S/C29S C4S/C60S C4S/C18S/C29S/C60S C18A/C29A C4A/C60A

A

B

Fig 4 Thermal and guanidine hydrochloride (GdnHCl)-induced

unfolding curves of the wild-type and its mutant proteins obtained

by fluorescence measurements (A) and (B) show the thermal and

guanidine hydrochloride unfolding curves of the wild-type and its

mutant proteins, respectively Experimental details are described in

Experimental procedures The thermal unfolding curve of the

wild-type treated with 0.1 M b-ME for reduction is indicated as

‘wild-type (reduced)’.

Table 1 Parameters characterizing the thermal denaturation of the wild-type and the three mutants Thermodynamic parameters were cal-culated from the thermal unfolding curves presented in Figs 4A and 5A All values are the averages of at least two determinations Data for the wild-type protein were reported by Kawamura et al [33] Errors are within ± 0.3 C for Tm , ± 5.5 kcalÆmol)1for DHm, and ± 0.016 kca-lÆmol)1K for DSmfor the wild-type protein, determined from four independent experiments Flu, fluorescence.

Protein Method DHm(kcalÆmol)1) DSm(kcalÆmol)1ÆK) Tm(C) DTm(C) DDG (kcalÆmol)1)

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effects of the introduction of the present mutations,

but is due mainly to deletion of the disulfide

bond(s)

We also examined the thermal stability of the wild-type treated with 0.1 m b-mercaptoethanol (b-ME) for reduction and compared it with those of the wild-type and mutant C4S⁄ C18S ⁄ C29S ⁄ C60S (Fig 4A and Table 1) The reduced wild-type exhibited a marked decrease in thermostability relative to the nonreduced wild-type of 14.4C (DDG: )4.85 kcalÆmol)1) The Tm value for the reduced wild-type was 46.2C, a value almost identical to that of the Cys-free mutant (Tm45.3C) No change was observed for the Cys-free mutant when it was melted in the presence of 0.1 m b-ME (data not shown)

In addition, the temperature dependence of the cata-lytic activity against (GlcNAc)5 for the Cys-free mutant was examined, and the result was compared with that for the wild-type (Fig 6) The wild-type protein exhibited the highest activity at 60C, and the activity was drastically reduced at 65C or above In contrast, the optimum temperature for the Cys-free mutant was decreased to 40C, which was about

20C lower than that of the wild-type, and a remark-able drop of the activity was observed above this temperature All of these results indicate that the two disulfide bonds are directly involved in the structural stability of G-type lysozyme Interestingly, the optimum temperature of the lytic activity for the floun-der G-type lysozyme was shown to be 25C by lyso-plate assay [23] Our results suggest that the low optimum temperature observed for the flounder lyso-zyme could be a consequence of the absence of the two intrachain disulfide bonds In the case of inverte-brate G-type lysozymes, the high content of Cys residues suggests their importance in protein stability

We noted that the decrease in the Tmvalue for mutant C4S⁄ C18S ⁄ C29S ⁄ C60S ()15.3 C) agreed well with the sum of the decreases in the Tm values for mutants C4S⁄ C60S and C18S ⁄ C29S ()15.8 C) The DCmvalue for the Cys-free mutant ()1.07 m) was also found to be

Table 2 Parameters characterizing the guanidine hydrochloride denaturation at pH 5.0 and 30 C Parameters were calculated from the gua-nidine hydrochloride unfolding curves presented in Figs 4B and 5B All values are the averages of at least two determinations Data for the wild-type protein were reported by Kawamura et al [33] Errors are within ± 0.03 M for Cm, ± 0.09 kcalÆmol)1Æ M for m, and ± 0.08 kcalÆmol)1 for DG H2O for the wild-type protein, determined from four independent experiments Flu, fluorescence.

Protein Method m (kcalÆmol)1Æ M ) Cm( M ) DCm( M ) DG H2O (kcalÆmol)1) DDG H2O (kcalÆmol)1)

–0.2

0

0.2

0.4

0.6

0.8

1.0

1.2

Temperature (ºC)

Wild-type (Flu) Wild-type (CD) C4S/C18S/C29S/C60S (Flu) C4S/C18S/C29S/C60S (CD)

–0.2

0

0.2

0.4

0.6

0.8

1.0

1.2

GdnHCl( M )

Wild-type (Flu) Wild-type (CD) C4S/C18S/C29S/C60S (Flu) C4S/C18S/C29S/C60S (CD)

A

B

Fig 5 Thermal and guanidine hydrochloride (GdnHCl)-induced

unfolding curves of the wild-type and mutant C4S ⁄ C18S ⁄

C29S ⁄ C60S obtained by CD and fluorescence measurements (A)

and (B) show the thermal and guanidine hydrochloride unfolding

curves, respectively Experimental details are described in

Experi-mental procedures The unfolding curves of the wild-type and

mutant C4S ⁄ C18S ⁄ C29S ⁄ C60S obtained with CD are indicated as

‘wild-type (CD)’ and ‘C4S ⁄ C18S ⁄ C29S ⁄ C60S (CD)’, respectively,

and those of the wild-type and mutant C4S ⁄ C18S ⁄ C29S ⁄ C60S

obtained with fluorescence are indicated as ‘wild-type (Flu)’ and

‘C4S ⁄ C18S ⁄ C29S ⁄ C60S (Flu)’, respectively.

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nearly equal to the sum of the DCm values for the

corresponding double mutants ()1.17 m) These findings

indicate that the effects on the protein stability of

delet-ing the disulfide bonds are approximately additive As

the locations of the two disulfide bonds are far from

each other in the crystal structure of GEL (Fig 1), the

individual disulfide bonds probably contribute to the

structural stability of G-type lysozyme in an

indepen-dent manner rather than in a cooperative manner

We can assume two mechanisms by which the

disul-fide bonds affect stability One is the entropic effect on

the unfolded forms, and the other is the effect of the

amino acid substitutions on the native forms

Theoreti-cal approaches have suggested that the entropic effect

(DS) will be related to the size of the loop enclosed by

the crosslink (n) A commonly used approximation is

that derived by Pace et al [34]: DS =)2.1–1.5 ·

R· ln n (calÆmol)1ÆK), where R is the gas constant

According to the equation, the increases in entropy in

the unfolded proteins caused by deletion of the Cys18–

Cys29 and Cys4–Cys60 disulfide bonds are 9.51 and

14.15 calÆmol)1ÆK, respectively In terms of free energy,

the expected entropic destabilization ()TDS) of

mutants C18S⁄ C29S and C4S ⁄ C60S is )3.17 and

)4.72 kcalÆmol)1, respectively, at the Tm value of the

wild-type at pH 5.0 (60.6C) These theoretical values are in good agreement with the observed DDG values for mutants C18S⁄ C29S ()3.11 kcalÆmol)1) and C4S⁄ C60S ()4.29 kcalÆmol)1) (Table 1) The sum of the theoretical values for the two double mutants ()7.40 kcalÆmol)1) is also comparable to the observed DDG value for the Cys-free mutant ()6.14 kcalÆmol)1) These results suggest that the increase in entropy of the unfolded state is a dominant factor determining the DDG In the case of the guanidine hydrochloride denaturation, the expected entropic destabilization at

30C is )2.88 and )4.29 kcalÆmol)1 for mutants C18S⁄ C29S and C4S ⁄ C60S, respectively These theo-retical values are close to but lower than the observed DDGH2O values for mutants C18S⁄ C29S ()2.33 kcalÆ mol)1) and C4S⁄ C60S ()3.33 kcalÆmol)1) (Table 2) However, as a small error in m results in a large devia-tion in DGH2O, due to a long extrapolation to 0 m denaturant, and as the concentration of guanidine hydrochloride at the midpoint of the denaturation (Cm) is regarded as the most reliable parameter for estimation of protein stability [55], the destabilization energies (DDGD) of the three mutants (C18S⁄ C29S, C4S⁄ C60S, and C4S ⁄ C18S ⁄ C29S ⁄ C60S) were recalcu-lated using the equation [56] DDGD= m¢(C¢m) Cm), where m¢ and C¢m are the values for the mutant, and

Cmis the value for for the wild-type The destabiliza-tion energies thus obtained are )2.66 and )4.09 kcalÆ mol)1 for mutants C18S⁄ C29S and C4S ⁄ C60S, respec-tively, which are in good agreement with the respective theoretical values The DDGD value for the Cys-free mutant ()6.83 kcalÆmol)1) is also nearly equal to the sum of the theoretical values for the corresponding double mutants ()7.17 kcalÆmol)1) These findings sug-gest that deletion of one or both of the disulfide bonds increases the conformational entropy of the unfolded state, thereby stabilizing the unfolded state and, as a result, destabilizing the protein thermodynamically This is in agreement with the proposal that stabiliza-tion of proteins by disulfide bonds can be essentially ascribed to a decrease of the conformational entropy

of the unfolded state Cooper et al [36] showed that the reduction in Tm resulting from selective disruption and modification of the Cys6–Cys127 disulfide bond of hen egg-white lysozyme is totally attributable to an increase in the entropy difference between the native and denatured states In contrast, Doig & Williams [57] reported, from a thermodynamic analysis on six small proteins, that the dominant effect of disulfide bonds on stability is enthalpic The thermodynamic characterization of a mutant human lysozyme lacking the Cys77–Cys95 disulfide bond showed that the decrease in DGH2O for the mutant protein was caused

Temperature (ºC)

0.0

0.1

0.2

0.3

0.4

0.5

0.6

0.7

0.8

0.9

1.0

10 20 30 40 50 60 70 80 90

Wild-type C4S/C18S/C29S/C60S

Fig 6 Temperature dependence of the catalytic activity for the

hydrolysis of (GlcNAc)5 by the wild-type and mutant

C4S ⁄ C18S ⁄ C29S ⁄ C60S The concentrations of hydrolyzed

(Glc-NAc)5 at each temperature were calculated by subtracting the

concentration of the remaining (GlcNAc)5 from that of the initial

(GlcNAc)5substrate.

Trang 8

by both entropic and enthalpic factors [37] Therefore,

detailed calorimetric measurements of the mutant

pro-teins will be required to determine the thermodynamic

parameters precisely

Heat inactivation

Next, we examined the stability against irreversible

heat inactivation for the wild-type and mutant

C4S⁄ C18S ⁄ C29S ⁄ C60S Unexpectedly, no difference

was observed in the irreversible heat inactivation of

these enzymes (data not shown) Both enzymes

regained 60% and 20% of their activities after 2 h at

80C and 90 C, respectively This is consistent with

the recent finding that the salmon G-type lysozyme

with no disulfide bonds, which has an optimum

tem-perature of 30C, regained 30% of its activity

immedi-ately after incubation at 90C for 3 h [25] As

suggested by Kyomuhendo et al [25], it appears that

OEL, as in the case of the salmon protein, possesses

an extraordinary capacity to correctly refold its

struc-ture When considered together with the result

obtained for the salmon protein, this indicates that,

probably, no disulfide bonds are required for the

fold-ing process of G-type lysozyme

Homology modeling and MD (molecular

dynamics) simulation

The tertiary structures of the wild-type and mutant

C4S⁄ C18S ⁄ C29S ⁄ C60S were constructed by homology

modeling on the basis of the X-ray structure of GEL [14] The Ramachandran plot provided by procheck ensured very good confidence for the wild-type and the mutant protein The reliabilities of the constructed structures were with 94.3% residues in the most favored regions and 5.7% in additional allowed regions There were no residues in the generously allowed regions and disallowed regions in the two proteins

Figure 7A shows the distribution of the B-factors

of the main chain atoms (N, Ca, C, and O) in the MD-generated average structural models of the wild-type and mutant C4S⁄ C18S ⁄ C29S ⁄ C60S The mole-cules are colored according to the B-factor, from dark blue for low B-factor to red for high B-factor Although the overall structure of the mutant was quite similar to that of the wild-type, an increase in B-factors throughout the molecule was observed in the Cys-free mutant This increase indicates that the conformation of the mutant protein becomes more flexible Figure 7B shows the plots of the B-factors

of the main chain atoms versus each residue for the wild-type and the Cys-free mutant All B-factors of the Cys-free mutant were substantially higher than those of the wild-type The average B-factors of the main chain atoms for the wild-type and the Cys-free mutant in the 200 samples obtained by the MD sim-ulations were 36.4 and 63.1 A˚2, respectively These findings suggest that the two disulfide bonds in G-type lysozyme act to keep the protein molecule folded tightly

A

B

Fig 7 (A) Residue flexibilities calculated

for the wild-type and mutant C4S⁄ C18S ⁄

C29S ⁄ C60S The ribbon diagram was

colored on the basis of the amplitudes of

fluctuations (B-factor) of individual residues.

A blue-to-red color spectrum is used to

represent different levels of flexibilities,

where the smallest motions are in blue and

the highest ones are in red (B) Amplitudes

of B-factors of each amino acid residue The

B-factors for the wild-type and mutant

C4S⁄ C18S ⁄ C29S ⁄ C60S are shown as blue

and pink lines, respectively The locations of

a-helices and b-sheets in the wild-type are

shown as red and sky-blue lines,

respec-tively The locations of the four Cys residues

are shown as green bars.

Trang 9

Our results demonstrated experimentally that the

indi-vidual disulfide bonds contribute significantly to the

structural stability of G-type lysozyme in an

indepen-dent manner The results also suggested that the

reduced stabilities caused by deletion of one or both

of the disulfide bonds are due mainly to entropic

effects The MD data showed that deletion of the

two disulfide bonds makes the protein conformation

more flexible It is thus speculated that the formation

of the disulfide bonds is involved in the structural

stability of G-type lysozyme by reducing the

confor-mational entropy of the unfolded state and by

increasing the rigidity of the protein molecule We

also found that deletion of both disulfide bonds does

not prevent the proper folding into the catalytically

active conformation of G-type lysozyme This

sug-gests that the formation of the two disulfide bonds of

G-type lysozyme occurs late in the folding process,

and that these disulfide bonds can be formed

inde-pendently rather than sequentially It is therefore

sug-gested that the structure around the mutation sites,

the N-terminal region in this case (Arg1–Cys60), may

not be responsible for the folding initiation site of

G-type lysozyme When the overall results are taken

into account, the two disulfide bonds of G-type

lyso-zyme may confer stability after the protein reaches its

final folded form in the absence of both disulfide

bonds On the other hand, we have shown that

G-type lysozyme has a structurally invariant core

composed of three a-helices (a5, a7, and a8) [20,21]

Previous investigations of protein folding suggested

that a-helical structures are formed at an early stage

in protein folding [58–63] As G-type lysozyme was

considered to require no disulfide bonds for folding

and function, we suppose that the three a-helices may

pack together in the early stage of the folding process

and act as nucleation sites around which the structure

can be formed

Experimental procedures

Materials

All enzymes used for DNA manipulation were purchased

from TaKaRa (Otsu, Japan) and Toyobo (Osaka, Japan)

The oligonucleotides used were from Hokkaido System

Sci-ence (Sapporo, Japan) Escherichia coli strain JM109 was

used for the transformation and propagation of

recombi-nant plasmids Multi-Copy Pichia Expression kits, including

expression plasmid pPIC9K and host strain GS115, were

obtained from Invitrogen (Carlsbad, CA, USA)

N-Acetyl-glucosamine oligosaccharides [(GlcNAc)n] were prepared by acid hydrolysis of chitin followed by charcoal celite column chromatography [64] M luteus cells were from Sigma (St Louis, MO, USA) Other reagents were of analytical or biochemical grade

Preparation of mutant proteins

Recombinant OEL with an extra Ser at the N-terminus was prepared as described previously [33] and used throughout this study as the wild-type It should be noted that the additional Ser residue at the N-terminus had little effect on the secondary structure, substrate-binding ability, lytic activity and structural stability of OEL [33] A plasmid harboring the wild-type sequence (pGSer–OEL) [33] was used as a template DNA for site-directed mutagenesis The oligonucleotide primers used were 5¢-GCCCTCGAGAAAAGATCTAGAACTGGATCT TACGGAG-3¢ for C4S, 5¢-GCCCTCGAGAAAAGATC TAGAACTGGAGCTTACGGAG-3¢ for C4A, 5¢-CAAA AGCTTTCTGTCGATCCAGC-3¢ for C60S, 5¢-CAAAAG CTTGCTGTCGATCCAGC-3¢ for C60A, 5¢-TCTTCTAA GTCTGCTAAGCCAGAAAAGCTGAACTACTCTGGA GTTG-3¢ for C18S ⁄ C29S, and 5¢-TCTGCTAAGTCTGC TAAGCCAGAAAAGCTGAACTACGCTGGAGTTG-3¢

method [65]) and verified by DNA sequencing Mutants

con-secutive rounds of mutagenesis To create the gene

described for the wild-type [33] The purity was

N-terminal amino acid sequence was determined with a Shimadzu model PPSQ21 sequencer (Shimadzu Co., Kyoto, Japan) The protein concentration was measured

by amino acid analysis with a Hitachi Model L-8500A amino acid analyzer (Hitachi High-Technologies Co., Tokyo, Japan)

CD spectra

spec-tropolarimeter (Japan Spectroscopic Co., Tokyo, Japan)

The data were expressed in terms of mean residue elliptic-ity The path-length of the cells was 0.1 cm for far-UV CD spectra (190–260 nm) Each spectrum was corrected by subtracting the spectrum of the buffer

Trang 10

Assay of enzymatic activity

assayed using lyophilized cells of M luteus as a substrate

One hundred microliters of lysozyme (final concentration

0.015 lm) was added to 3 mL of a suspension of M luteus

adjusted to A 0.9 at 540 nm with 0.1 m sodium phosphate

the first 5 min of linear decrease in absorbance at 540 nm

mixture, containing 0.1 mm lysozyme and 1 mm (GlcNAc)5,

was incubated in 10 mm sodium acetate buffer (pH 4.0)

After a given reaction time, 200 lL of the reaction mixture

was withdrawn and rapidly chilled in a KOOL KUP

(Towa, Tokyo, Japan) The reaction mixture was

centri-fuged at 4000 g for 1h with Ultrafree C3LGC (Millipore,

Billerica, MA, USA), and the filtrate was lyophilized The

dried sample was dissolved in 50 lL of ice-cold water,

and then 10 lL of the solution was applied to a TSKgel

in a JASCO 800 series HPLC column Elution was

per-formed with distilled water at room temperature and a flow

concentra-tion was calculated from the peak area monitored as the

UV absorption at 220 nm, using the standard curve

obtained for authentic saccharide solutions The relative

the recovered concentration of all chito-oligosaccarides in

The temperature dependence of the catalytic activity for

in 10 mm sodium acetate buffer (pH 4.0) and incubated at

various temperatures for 5 min Then, the enzyme dissolved

in the same buffer was added, and the activity was

mea-sured at the designated temperature for 30 min (wild-type)

Thermal unfolding

Reversible thermal unfolding was monitored by CD and

fluorescence measurements as described previously [33] CD

measurements at 222 nm were performed with a

Jas-co J-600 spectropolarimeter using a 0.1 cm cuvette The

flu-orescence intensities at 360 nm, excited at 280 nm, were

measured with a Hitachi F-4500 Fluorescence

sodium acetate buffer (pH 5.0) containing 0.5 m guanidine

hydrochloride These conditions were chosen for complete

reversibility of the thermal denaturation [33] In the

solution of the reduced wild-type, 0.1 m b-ME was also added The water-jacketed cell containing each sample was heated for 5 min at a given temperature by a thermostati-cally regulated circulating-water bath All samples were fully equilibrated at each temperature before measurement The temperature of sample solutions was directly measured using a TX1001 thermometer (Yokokawa M&C Co., Tokyo, Japan) To facilitate comparison between the two sets of unfolding curves, the experimental data were normalized as follows The fraction of unfolded protein was calculated from either the CD values or fluorescence intensities by linearly extrapolating the pretransition and post-transition base lines into the transition zone, and then plotted against temperature Assuming that the unfolding equilibrium involves a two-state mechanism, the unfolding curves were subjected to a least squares analysis to deter-mine the midpoint temperatures (Tm) and thermodynamic

are negligible compared to DSm, the difference in the free

between the mutant and wild-type proteins (DDG) was

proteins

Guanidine hydrochloride unfolding

Guanidine hydrochloride-induced unfolding curves were also determined by monitoring two different parameters at

is the intrinsic fluorescence (excitation at 280 nm and

acetate buffer (pH 5.0) with varying concentrations of

fully equilibrated at each denaturant concentration before

under these conditions, and the unfolding data were analyzed on the basis of a two-state model From the guanidine hydrochloride unfolding profiles, the difference

in free energy change between the folded and unfolded states (DG) was calculated according to Pace [55] The free

DG on the guanidine hydrochloride concentration (m) were determined by least squares fitting of the data for the

m[gua-nidine hydrochloride] The guam[gua-nidine hydrochloride con-centration at the midpoint of the transition (DG = 0) was

wild-type and mutant proteins were calculated by subtract-ing the value of the wild-type from those of mutant proteins

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