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falciparum enolase dimer interface with respect to mammalian enolases could be exploited to selectively dissociate the dimeric parasite enzyme into its catalytically inefficient, thermall

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versus yeast and mammalian enolases to dissociation into active monomers

Ipsita Pal-Bhowmick, Sadagopan Krishnan and Gotam K Jarori

Department of Biological Sciences, Tata Institute of Fundamental Research, Colaba, Mumbai, India

Enolase (EC 4.2.1.11) is a glycolytic enzyme that

cata-lyzes the interconversion between

2-phospho-d-glycer-ate (PGA) and phosphoenolpyruv2-phospho-d-glycer-ate Enolases from

most organisms exist as homodimers of subunit mass

40–50 kDa [1], the exceptions being homo-octameric

enolases from thermophilic bacteria [2–4] A variety of

physical data indicate that each dimer contains two

active sites The active site in each subunit is

com-pletely independent [5,6] As the active site is fully

contained in each subunit, attempts to dissociate the

dimeric form into an active monomeric form have been made using genetic [7], chemical and physical methods, but without much success Although dissociation of the dimer could be achieved, the monomers formed were found to be inactive [8–11] The formation of act-ive monomers was inferred under conditions of high temperature (40–45C) and low protein concentration (in the nanomolar range) [12,13] However, at such low concentrations, neither the kinetic nor the struc-tural characterization of the monomer could be carried

Keywords

enolase; monomers; Plasmodium

falciparum; rabbit muscle; yeast

Correspondence

G K Jarori, Department of Biological

Sciences, TIFR, Homi Bhabha Road, Colaba,

Mumbai 400 005, India

Fax: +91 22 22804610

Tel: +91 22 22782000

E-mail: gkj@tifr.res.in

(Received 7 December 2006, revised 16

January 2007, accepted 12 February 2007)

doi:10.1111/j.1742-4658.2007.05738.x

In the past, several unsuccessful attempts have been made to dissociate homodimeric enolases into their active monomeric forms The main objective

of these studies had been to understand whether intersubunit interactions are essential for the catalytic and structural stability of enolases Further motivation to investigate the properties of monomeric enolase has arisen from several recent reports on the involvement of enolase in diverse non-glycolytic (moonlighting) functions, where it may occur in monomeric form Here, we report successful dissociation of dimeric enolases from Plas-modium falciparum, yeast and rabbit muscle into active and isolatable monomers Dimeric enolases could be dissociated into monomers by high concentrations ( 250 mm) of imidazole and ⁄ or hydrogen ions Two forms were separated using Superdex-75 gel filtration chromatography A detailed comparison of the kinetic and structural properties of monomeric and dimeric forms of recombinant P falciparum enolase showed differences in specific activity, salt-induced inhibition and inactivation, thermal stability, etc Furthermore, we found that enolases from the three species differ in their dimer dissociation profiles Specifically, on challenge with imidazole, Mg(II) protected the enolases of yeast and rabbit muscle but not of

P falciparum from dissociation The observed differential stability of the

P falciparum enolase dimer interface with respect to mammalian enolases could be exploited to selectively dissociate the dimeric parasite enzyme into its catalytically inefficient, thermally unstable monomeric form Thus eno-lase could be a novel therapeutic target for malaria

Abbreviations

M im , imidazole-generated monomer; M nt , native monomer; M pH , pH-generated monomer; 2-PGA, 2-phospho- D -glycerate; RMen, rabbit muscle enolase; r-Pfen, recombinant Plasmodium falciparum enolase; Yen, yeast enolase.

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out Hydrostatic pressure, which is viewed as a gentle

and reversible perturbation, has also been employed in

attempts to obtain active monomers from dimeric

eno-lase [8,11,14–17] Although the dissociation of enoeno-lase

dimers into active monomers was inferred in some of

the above studies, it has never been unequivocally

demonstrated As none of these attempts had resulted

in the isolation of active monomers and their

charac-terization, it was not clear whether the monomeric

form is intrinsically inactive or the means of

dissoci-ation selectively inactivated it Suggestions have also

been made that intersubunit interactions may be

essen-tial for completion of the catalytic cycle In recent

years, enolase has also been shown to participate in a

variety of nonglycolytic (moonlighting) biological

func-tions [18] The oligomeric state of enolase recruited for

the moonlighting functions is not known

Our interest in the enolase from the malarial

para-site (Plasmodium falciparum) originates from the fact

that the intraerythrocytic stages of the parasite lack

active mitochondria and hence rely solely on glycolysis

for their energy needs [19,20] The level of glycolytic

flux in parasite-infected cells is  50–100-fold greater

than that in uninfected red blood cells, and the activity

of many glycolytic enzymes is upregulated, enolase

being one of them [21–23] P falciparum enolase (Pfen)

could be a potential drug target, as there is only one

gene for this enzyme, and it shows greater resemblance

to plant enolases than to mammalian enolases In

order to examine such possibilities and explore

whe-ther it has any moonlighting functions, we have

recently cloned the P falciparum enolase gene,

over-expressed it, and obtained pure protein [24] We have

also raised polyclonal and monoclonal antibodies

against recombinant r-Pfen for subcellular localization

studies [25] Our observations have shown a diverse

subcellular localization (enolase is associated with

plasma membrane, cytosol, cytoskeletal elements and

nucleus; unpublished results) for enolase, indicating

that it may be recruited for certain other nonglycolytic

functions

One of the conventional approaches in rational drug

design has been to make active site-specific inhibitors

that can differentiate between host and parasite

pro-teins and bring about selective inhibition of the

para-site enzyme The major limitation of this strategy is

that active sites are evolutionarily highly conserved,

and structural differences may be rather subtle or even

nonexistent As there are numerous protein–protein

interactions that operate in living systems [26–28], and

most proteins exist as oligomers [29] with a

predomin-ance of homodimers [30], another approach could

be to target protein–protein interfaces for perturbing

protein and cell functions [31] In cases where oligo-meric structure is essential for biological activity, selective disruption of such an interface in a protein of parasite origin can have therapeutic effects Rationally designed peptides that can compete for the interaction between monomeric subunits (peptidomimetics) have yielded encouraging results [32–35] Attempts have also been made to find nonpeptide small molecule inhibi-tors that effectively interfere with protein–protein interactions [36–38] Here, we have examined the possi-bility of dissociating malarial parasite enolase into monomers using small molecules, and characterized the properties of the monomeric state We report the successful dissociation of r-Pfen, and yeast and rabbit muscle enolases, into isolatable active monomers Thus

we demonstrate that the dimeric structure is not essen-tial for catalysis However, comparative kinetic and structural studies on the monomeric and dimeric forms

of r-Pfen showed several interesting differences The monomeric form has low specific activity, is more ther-molabile, and is more prone to lose activity in the presence of salts as compared to the dimer Our experi-ments have also identified conditions under which selective dissociation of the parasite enolase may be accomplished Although the concentrations of dissoci-ating ligand used in this study are rather high and unrealistic for therapeutic applications, the possibility remains that such differences may be exploitable for targeting this enzyme for therapeutic purposes

Results

Imidazole-induced dissociation of r-Pfen into active monomers

Like most enolases, r-Pfen is a homodimer of two

50 kDa subunits [24] Purified dimeric r-Pfen was dia-lyzed against increasing concentrations (0–250 mm) of imidazole and then subjected to gel filtration chroma-tography on a Superdex-75 column Figure 1A shows gel filtration chromatograms obtained at several differ-ent concdiffer-entrations of imidazole at pH 6.0 A dimer peak was observed in the absence of imidazole How-ever, with increasing concentrations of imidazole, the monomeric fraction increased, and at  250 mm imidazole, > 95% of r-Pfen was dissociated The effect

of pH on imidazole-induced dissociation was examined

by dialyzing the enzyme against 50 mm sodium phos-phate at different pH values (6.0, 7.0 and 8.0) with increasing concentrations of imidazole The percentage

of monomer present in each of these samples was determined from gel filtration chromatograms The results presented in Fig 1B show that lower pH

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favored the dissociation of r-Pfen Figure 1C shows a

gel filtration chromatogram of a sample dialyzed

against 250 mm imidazole in 50 mm sodium phosphate

(pH 6.0) The enzyme activity of each fraction was

measured, and the specific activity was plotted along

with protein concentration (A280) as a function of

elu-tion volume The results showed that both forms

(monomeric and dimeric) were catalytically active, with

the dimer having 3-fold greater specific activity than

the monomer Experiments were also performed in

which the effects of adding NaCl to the dissociation

buffer were examined The results showed that

the presence or absence of salt (300 mm NaCl) did

not have any effect on monomer–dimer equilibrium

Imidazole-generated monomers of r-Pfen (Mim)

( 10 lm), when extensively dialyzed against

imida-zole-free buffer, could reassociate to form active

dimers To the best of our knowledge, this is the first

demonstration of obtaining active monomers of

enolase that could be separated from dimers

The ability of imidazole to dissociate enolases from

other species was also examined Imidazole at 250 mm

and pH 6.0 failed to dissociate yeast enolase (Yen)

However, inclusion of 300 mm NaCl along with

250 mm imidazole at pH 6.0 resulted in almost

com-plete dissociation of Yen (Fig 2A) In the case of

rab-bit muscle enolase (RMen), 250 mm imidazole did not

dissociate the enzyme As commercial preparations of

RMen contain Mg(II), we included 5 mm EDTA along

with imidazole This resulted in partial dissociation of

0

75

[Imidazole]

50 m M

250 m M

150 m M monomer

0 50

Ve (ml)

0 m M dimer

0 2 0 50

A r-Pfen

Ve (ml)

50 55 60 65 70 75 80 0

40 80

0 2 4

6 ) g

B

0 25 50 75 100

0 50 100 150 200 250 [Imidazole](m M )

pH 6.0

pH 7.0

pH 8.0

C

Fig 1 Imidazole-induced dissociation of r-Pfen (A) Superdex-75 gel filtration chromatograms obtained at different concentrations of imida-zole Enzyme (0.5 mg) was dialyzed ( 14 h) against 50 m M sodium phosphate (pH 6.0) containing different amounts (0–250 m M ) of imida-zole The column was pre-equilibrated with appropriate buffer, and chromatography was performed at room temperature (20 ± 1 C) (B) Effect of pH on imidazole-induced dissociation of r-Pfen Each data point is an average of two chromatographic runs (C) Gel filtration chro-matogram of r-Pfen in 50 m M sodium phosphate containing 250 m M imidazole (pH 6.0) A 280 nm and specific activity (r—r) for each fraction are shown.

Yen

0 3

(a)

monomer

Ve(ml)

0 10

dimer

dimer

(b) 0 2

(c)

RMen

B A

0 35

0

15 (c) (b) (a)

Ve(ml)

0 2

dimer monomer

dimer

dimer

Fig 2 Imidazole-induced dissociation of Yen and RMen Samples were in 50 m M sodium phosphate (pH 6.0), and 0.2–0.6 mg of protein was used for each chromatographic run on a Superdex-75 column (A) Yen: (a) no imidazole; (b) 250 m M imidazole; and (c) 250 m M imidazole + 300 m M NaCl (B) RMen: (a) no imidazole; (b) 250 m M imidazole; and (c) 250 m M imidazole + 5 m M EDTA.

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RMen (Fig 2B) However, further inclusion of

300 mm NaCl did not lead to complete dissociation of

RMen In this respect, RMen differs from Yen

As Mg(II) is an essential cofactor for stabilization of

the active conformation and catalysis, extensive kinetic

and direct metal ion-binding studies have been

per-formed in the past These studies have shown that each

enolase subunit has three binding sites for the divalent

cation, namely a conformational site (site I), a catalytic

site (site II) and an inhibitory site (site III) [39–42] As

binding of divalent cation induces large

conforma-tional changes in enolase, we examined the effect of

Mg(II) on imidazole-induced dissociation of r-Pfen,

Yen and RMen in the presence of different

com-pounds The results are summarized in Table 1

Inclu-sion of EDTA [to chelate residual Mg(II) in the

protein sample] and NaCl in the dissociation buffer

did not have any effect on the dimeric state However,

the presence of Mg(II) affected the imidazole-induced

(or imidazole + NaCl-induced) dissociation of RMen

and Yen It is interesting to note that in the presence

of 1.5 mm MgCl2, imidazole could dissociate r-Pfen

but had no effect on Yen and RMen

pH-induced dissociation of enolases The effect of pH on the oligomeric state of enolases was examined by performing gel filtration chromatog-raphy on the enzyme, dialyzed against 50 mm sodium phosphate of the desired pH Figure 3A presents the chromatographic profiles of r-Pfen in the pH range 4.5–8.0 Figure 3B shows that 50% dissociation of r-Pfen occurs around pH 5.5 Monomeric r-Pfen gener-ated by low pH (MpH) was also found to be enzymati-cally active (see below) Low pH could also dissociate Yen and RMen The half-dissociation point for Yen was around pH 5 (Fig 3C,D), whereas for RMen it was around pH 5.5 (Fig 3E,F)

Activity and reassociation of MpHand Mim Measurements of enzyme activity in monomeric and dimeric fractions showed that Mim had  3-fold less specific activity than dimers (Fig 1C) As the assay solution did not contain imidazole, it is possible that the observed activity of Mim may have arisen from reassociation to dimers Similarly, MpH could also reassociate at the assay solution pH of 7.4 Such reassociation of monomers into dimers during an enzyme assay would result in an increase in the slope

of the reaction progress curve (as the dimer is  3-fold more active than monomers) From these considera-tions, we can state that during an enzyme assay using

MpHor Mim: (a) if there is reassociation of monomers into dimer on the timescale of the enzyme assay, the reaction progress curve will exhibit a time-dependent increase in slope; and (b) as the amount of dimer formed increases as the square of the monomer con-centration, a plot of monomer concentration versus activity would have an upward curvature if there was

a significant amount of dimer formed during the enzyme assay

Figure 4A shows the reaction progress curves at three different concentrations of MpH (0.04, 0.17 and 0.43 lm) The observed increase in slope with time sug-gests reassociation of MpHinto dimers under our assay conditions A similar experiment performed using

Mim (Fig 4B) did not show any change in slope with time We measured the concentration dependence of specific activity for MpH at time  0.0 min as well as

at time > 1 min (Fig 4C) The first slope reflects the monomer activity, whereas the slope determined after > 1 min reflects the dimer activity With the increasing concentration of MpH, initially we observed

a very low specific activity ([MpH] > 0.5 lm) However,

at higher protein concentrations, the rate of formation

of dimer increased rapidly, and only a single slope,

Table 1 Effect of Mg(II) on monomer–dimer equilibrium in enolase.

Enolase, 10 l M (0.5 mgÆmL)1), was dialyzed against 50 m M

sodium phosphate (pH 6.0) containing different compounds as

indi-cated below Concentrations of these compounds when used

were: [imidazole] ¼ 250 m M ; [EDTA] ¼ 5 m M ; [NaCl] ¼ 300 m M ;

[MgCl 2 ] ¼ 1.5 m M The Superdex-75 column was pre-equilibrated

with the same buffer as used for dialysis.

Enolase

Dimeric–monomeric states of enolasesa

P falciparum (r-Pfen)

Yeast (Yen)

Rabbit muscle (RMen)

+ Imidazole + EDTA Monomer Dimer Partial

monomer + Imidazole + NaCl Monomer Monomer Partial

monomer + MgCl2+

imidazole + NaCl

+ MgCl 2 +

imidazole + EDTA

monomer + MgCl2+

imidazole +

EDTA + NaCl

Monomer Monomer Partial

monomer

a

When the amount of dimer or monomer is ‡ 90%, it is stated as

‘dimer’ or ‘monomer’ When the amount is ‡ 40%, it is stated as

‘partial monomer’.

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characteristic of dimer-specific activity, could be

observed (Fig 4C) As in the low-concentration range

of MpHthe observed activity is rather small, it is likely

that either MpHis inactive and the measured activity is

a reflection of the formation of tiny amounts of active

dimer, or the MpH has intrinsically very low activity

Irrespective of these two possibilities, the observed

sec-ond slope reflects the activity for the dimer formed

during the assay As expected, the specific activity

computed using the second slope did not exhibit the

monomer concentration-dependent variation (Fig 4C)

These results indicate that MpH rapidly reassociates to

form dimer However, similar measurements of

con-centration dependence of activity for Mimgave a linear

increase in activity, suggesting that r-Pfen Mimdid not

associate rapidly (with respect to assay timescale) to

form more active dimers (Fig 4D) A replot of these

data as specific activity versus Mim concentration (Fig 4D) showed that the observed specific activity was low ( 1.8–1.9 unitsÆmg)1, a characteristic of Mim) and was concentration invariant on enzyme assay time-scales These observations support the view that Mim associates slowly to form dimers, whereas MpH associ-ates rapidly Thus MpHand Mimdiffer in their ability

to reassociate, indicating that they represent two differ-ent conformational states of the monomeric form of the enolase A schematic representation of the dissoci-ation and associdissoci-ation of r-Pfen is presented in Scheme 1, where Mnt is the native monomer, which is assumed to be the only monomeric form that can dimerize As Mim mostly remained in the monomeric state under our assay conditions, kinetic characteriza-tion of the monomeric forms of enolase was performed using Mimonly

D

A

Fig 3 pH-induced dissociation of enolases from different organisms Each enzyme (0.2–0.6 mg) was dialyzed against 50 m M sodium phos-phate (pH 4.5–8.0) containing 150 m M NaCl and subjected to gel filtration chromatography (A) Gel filtration profile of r-Pfen at different pH values (B) pH versus % monomer (data are from two different experiments) for r-Pfen The r-Pfen used here was prepared by eluting the protein from Ni–nitrilotriacetic acid resin at low pH (C) Gel filtration chromatograms for Yen (D) pH versus% monomer for Yen (E) Gel filtra-tion chromatograms for RMen (F) pH versus % monomer for RMen.

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MpH from Yen and RMen also showed nonlinear

reaction progress curves, very similar to those observed

for r-Pfen (data not shown) In enzyme assays, Mim

from Yen gave nonlinear reaction progress curves

dis-playing an increase in slope with time This is likely to

be due to Mg(II)-induced rapid dimerization of yeast

Mim As Mg(II) does not affect the dimerization of

r-Pfen monomers, such a change of slope was not

observed for Mim prepared from r-Pfen (Fig 4B)

Observed low activities of monomeric (Mimand MpH)

enolases from all three species would imply that

quater-nary interactions between two subunits stabilize

cata-lytically more active conformations of each subunit

Comparison of kinetic properties of monomeric

(Mim) and dimeric forms of r-Pfen

As Mim did not reassociate rapidly into dimers, this

form of the enzyme was used for comparative kinetic

studies Figure 5A shows the variation of enzyme activ-ity as a function of phosphoenolpyruvate concentration Data were fitted to the Michaelis–Menten equation using sigmaplot software The nonlinear fit of data gave Vmax¼ 13.5 ± 0.5 UÆmg)1, and Km (phospho-enolpyruvate)¼ 0.28 ± 0.03 mm for dimers, and

Vmax¼ 3.7 ± 0.3 UÆmg)1, and Km (phosphoenolpyru-vate)¼ 0.38 ± 0.07 mm for monomers, respectively Thus disruption of subunit–subunit interactions resulted

in a significant decline in enzyme activity ( 3-fold), but did not have much effect on Km We also compared the thermal stability of monomeric (Mim) and dimeric forms Equal amounts of protein were incubated at three different temperatures (4C, 37 C and 50 C), and activity was assayed at different time intervals The dimeric form was stable for a prolonged (£ 250 min) duration at 37C, and showed  20–25% inactivation

at 50C In comparison, the monomeric form was

 80% inactivated at 37 C (£ 250 min) and completely

0.00 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.50 1.379

1.39 1.40 1.41 1.42 1.43 1.44 1.45 1.464

B Imidazole monomer (Mim):

reaction progress curves

Time (minutes)

0.13

0.33

0.6 0.00 0.2 0.4 0.6 0.8 1.0 1.2 1.4 1.50

1.255

1.28

1.30

1.32

1.34

1.354

A pH monomer (MpH):

reaction progress curves

Time (minutes)

0.04

0.17

0.43

( µ M )

( µ M )

D Imidazole monomer (Mim):

concentration dependence of activity

C pH monomer (MpH):

concentration dependence of activity

0.05 0.10 0.15 0.20 0.25 0.30 0.35 0.40

0.6 0.8 1.0 1.2 1.4 1.6 1.8

[Monomer] ( µ M )

–1 )

[Monomer] ( µ M )

0.0

0.5

1.0

1.5

2.0

Fig 4 Reaction progress curves for the monomeric r-Pfen-catalyzed reaction Conversion of phosphoenolpyruvate to 2-PGA was monitored

at 240 nm (A) MpH (B) Mim Note the time-dependent change in progress curve slopes in (A) (C) Variation in specific activity as a function

of [M pH ], calculated from first (time  0.0 min) (d) and second (time > 1 min) (j) slopes of reaction progress curves Note the change in specific activity computed from the time  0.0 min slope, reflecting the rapid formation of dimer at higher concentrations of M pH (D) Vari-ation in activity (and specific activity) as a function of [Mim] Activity showed a linear increase (o), with specific activity remaining constant (d), suggesting that M im did not associate to form high-activity dimer on the enzyme assay timescale.

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inactivated at 50C in £ 150 min (Fig 5B) Thus,

subunit–subunit interface interactions confer higher

thermal stability to the protein

As enolases from different organisms are known to

differ in their response to different salts [43], we

exam-ined the effect of various salts on the catalytic activity of

the monomeric and dimeric forms To assess the effect

of a salt, we assayed the enzyme with assay

mix-tures containing different concentrations of a salt

Figure 6A–C shows the effects of NaCl, KCl and KBr

on the activity of the dimeric and monomeric (Mim)

forms of r-Pfen NaCl inhibited both forms of the

enzyme, but the inhibition was stronger for the

mono-meric form (Fig 6A) In the case of KCl and KBr, the

dimeric form was mildly activated ( 10–20%), whereas

the monomeric form was strongly inhibited (Fig 6B,C)

For assessing the activating⁄ inactivating effect of the

salts (NaCl, KCl and KBr), the enzyme was incubated in

buffer containing several different concentrations of salt

for 24 h at 20 ± 1C, and then assayed in the absence

of the salt The results are presented in Fig 6D–F At

median concentrations ( 300 mm), NaCl and KCl had

an activating effect on the dimeric form of the enzyme,

whereas all three salts had a concentration-dependent

inactivating effect on the monomeric form

Comparison of CD and fluorescence spectra

of monomeric and dimeric enolase

The effect of the loss of subunit–subunit interface

interactions on the secondary and⁄ or tertiary structure

of enolase was probed by recording CD and fluores-cence spectra of monomeric and dimeric forms of the protein As monomer preparations made by imidazole treatment contain about 250 mm imidazole, which interferes with fluorescence and CD spectra, it was not possible to record meaningful spectra for Mim Instead,

we recorded CD and fluorescence spectra for r-Pfen and Yen MpH, and compared them with the spectra from dimers (Fig 7) CD spectra of monomeric and dimeric forms (r-Pfen and Yen) were very similar (Fig 7A,C) Analysis of r-Pfen CD spectra using the

[PEP] (m M )

1-)

0 2 4 6 8 10

B A

Time (min)

0.0 0.2 0.4 0.6 0.8 1.0 1.2 1.4

Fig 5 (A) Comparison of monomer and dimer activity with varying concentrations of phosphoenolpyruvate For activity measurements,

50 lL of 2 l M r-Pfen (monomeric or dimeric) was added to 450 lL

of assay mixture As monomeric protein was in 250 m M imidazole, the final concentration of imidazole in the assay mixture was

25 m M The presence of 25 m M imidazole in the assay mixture had

no effect on dimer activity Data were fitted to the Michaelis– Menten equation The best-fit parameters are K m (phos-phoenolpyruvate) ¼ 0.38 ± 0.07 m M and Vmax (specific activity) ¼ 3.7 ± 0.3 UÆmg)1 for monomer (j), and K m (phosphoenolpyru-vate) ¼ 0.28 ± 0.03 m M and V max ¼ 13.5 ± 0.5 UÆmg)1 for dimer (h) (B) Temperature dependence of stability of dimeric (open sym-bols) and monomeric (Mim) (filled symbols) forms of r-Pfen Enzyme was incubated at 4 C (s or d), 37 C (n or m) and 50 C (h or

j ) The activity was assayed at different time intervals.

+H + (slow) -H + (fast)

pH monomer

Imidazole

monomer

Native monomer

Native

+ imidazole

(slow)

-imidazole

(slow)

Scheme 1 Schematic representation of dissociation of the dimeric

(D) form of enolase to the imidazole-induced and pH-induced

mono-meric (Mimor MpH) forms The dimer is shown to dissociate into

the native form (M nt ), which has an enzyme activity similar to that

of the dimer Lowering of the pH or addition of imidazole (or both)

stabilize different conformations of monomers Mimand MpHdiffer

in activity and stability from the dimer and M nt M pH is rapidly

con-verted into M nt on raising of the pH, whereas M im is slow to

con-vert to Mnt, a form that is competent to form dimers.

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cdnn program for secondary structure analysis [44]

gave helix 36.6%, beta 14.1%, turn 19.3% and

ran-dom 29.9% for the dimeric form, and helix 31.5%,

beta 18.3%, turn 18.4% and random 31.8% for the

monomeric form Thus, it appears that dissociation of

dimers to form monomers lead to a slight decrease in

helical content with a concomitant increase in the beta

sheet content

Fluorescence emission spectra of the monomic,

dimeric and denatured states of r-Pfen and Yen are

shown in Fig 7B,D For both of these enzymes,

disso-ciation of enolase into monomers led to a decrease in

emission intensity In the case of r-Pfen, the emission

maximum was blue-shifted upon dissociation (Fig 7B;

compare traces a and b), whereas for Yen, a slight red

shift was observed (Fig 7D) Such a red shift may

arise because the dimer interface of Yen has Trp56

(which becomes solvent-exposed upon dissociation),

whereas the analogous position in Pfen is occupied by

Tyr59

Discussion

Alignment of enolase sequences from several different

organisms have shown that it is a highly conserved

protein [18] Furthermore, the comparison of known

three-dimensional structures showed complete

posi-tional conservation of active site residues across species [5,6,41,45–49] The enolase polypeptide chain folds into two domains, with the small domain having a mixture

of a-helices and b-sheets, and the large domain having

an a⁄ b-barrel structure (Fig 8D) The binding of sub-strate brings these two domains together to constitute

an active site As most enolases are homodimeric, the intersubunit interface is formed by contacts between the small domain of one subunit and the large domain

of the other subunit If the subunit–subunit interface is large, the dissociated monomers are generally unstable, due to exposure of large hydrophobic surfaces to the solvent [50] The intersubunit interface in enolases is rather small ( 11–13% buried surface) and quite hydrophilic, suggesting that it may be possible to dis-sociate the dimer into active monomers

In the past, several attempts have been made to dis-sociate the dimeric enolase into active monomers [7–9,11,14–17] However, the active monomeric form could never be obtained in isolation from the dimeric form Failure to obtain active monomers of enolase strengthened the belief that enolases are active only in the dimeric state [51] and that the quaternary structure

of enolase is necessary for catalytic activity Thus, any attempt to dissociate the dimer is accompanied by changes in the tertiary and secondary structures that are detrimental to enzyme activity [8] However, the

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Fig 6 Effect of NaCl, KCl and KBr on the activity of monomeric (Mim) (j) and dimeric (h) r-Pfen Upper panel (a, b, c): Enzyme samples were assayed in the presence of different concentrations of salts Lower panel (d, e, f): Enzyme samples (200 lL of 2 l M r-Pfen) containing different concentrations of salts were incubated for 24 h at 20 C, and assayed in the absence of the salt For each assay, 50 lL of the enzyme was added to 450 lL of the assay mixture Activity is expressed as percentage of control where no salt was added to the enzyme sample.

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results presented here unequivocally establish that both

H+and imidazole are able to dissociate enolase dimers

into active monomers that could be isolated from the

dimeric form (Figs 1–3) We observed that at any

given concentration, the ability of imidazole to

dissoci-ate the dimer was enhanced by low pH (Fig 1B) In

the absence of imidazole, a change in pH (in the range

6–8) did not have any significant effect on the

dissoci-ation of the enzyme (Fig 1B), suggesting that the

increased dissociation induced by imidazole at low pH

is mostly due to pH-dependent ionization of imidazole

Imidazole has a pKaof 6.9, and hence at pH 6.0 it will

exist predominantly as an imidazolium ion Thus, the

data presented in Fig 1B are commensurate with the

idea that it is the imidazolium ion that is effective in

dissociating the r-Pfen dimer into monomers (Mim)

The pH-dependent dissociation of various enolases

indicate that it is the protonation of group(s) at the

intersubunit interface with a pKa 5–5.5 that is

responsible for the dissociation (Fig 3)

An examination of the enolase intersubunit interface

showed that it is stabilized by two salt bridges, several

hydrogen bonds, and p–cation (Tyr or Trp-Arg) and hydrophobic interactions A relatively low contribution

of the salt bridge in stabilizing the dimer interface was evident from the fact that replacement of an interface glutamate residue with a leucine (E414L) in RMen did not result into the dissociation of dimer DGo for dissociation for the mutant enzyme decreased from 49.7 kJÆmol)1to 42.3 kJÆmol)1[7] One may ask the fol-lowing question: which are the subunit interface inter-actions that imidazolium and⁄ or hydrogen ions can possibly disrupt? An examination of the intersubunit interface suggests the following two possibilities (a) There is a hydrogen bond between His191 NE2 and the carbonyl oxygen of Gly15 (or Arg14) where His191 NE2 acts as a proton donor (Fig 8A,B) Imidazole, being an analog of histidine, can compete for this hydrogen bond The importance of this interaction in stabilizing the dimer is evident from the observed chan-ges in the intersubunit hydrogen bond pattern on Mg(II) binding In one Mg(II)-bound form of Yen (Protein Data Bank: 2ONE, 1EBH), a hydrogen bond forms between His191 and Arg14 (Fig 8B) with a bond

-14000 -12000 -10000 -8000 -6000 -4000 -2000 0 2000 4000

1-Wavelength (nm)

-14000

-12000

-10000

-8000

-6000

-4000

-2000

0

2000

4000

1-)

Wavelength (nm)

Wavelength (nm)

0

1e+8

2e+8

3e+8

4e+8

5e+8

6e+8

7e+8

a b

c

Wavelength (nm)

0.0 5.0e+7 1.0e+8 1.5e+8 2.0e+8 2.5e+8 3.0e+8

3.5e+8

a b c

Yen r-Pfen

a

Yen

a b

r-Pfen

b

Fig 7 Comparison of CD and fluorescence spectra of monomeric (MpH) and dimeric forms of r-Pfen and Yen (A) CD spectra of (a) dimer and (b) monomer of r-Pfen (B) Fluorescence spectra of (a) dimer, (b) monomer and (c) urea-denatured r-Pfen (C) Yen CD spectra: (a) dimer, (b) monomer (D) Fluorescence spectra of (a) dimer, (b) monomer and (c) urea-denatured Yen Fluorescence emission intensities were nor-malized for protein concentration.

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length (as measured between two non-hydrogen atoms

in the hydrogen bond) of 3.2–3.3 A˚ In two

Mg(II)-bound forms (Protein Data Bank: 1ONE, 1EBG), the

hydrogen bond is between His191 and Gly15 (Fig 8A)

with a bond length of 2.9–3.0 A˚ Thus, the loss of

Mg(II) may favor weaker hydrogen bonds and

dissoci-ation, whereas addition of Mg(II) may reverse the

pro-cess, leading to subunit–subunit association It is

interesting to note that in the neuronal enolase crystal

structure (Protein Data Bank: 1TE6), where one

sub-unit is bound to one Mg(II) ion and the other subsub-unit

has two Mg(II) ions, both types of hydrogen bond

(His–Gly and His–Arg) are observed (Fig 8C) Our observations that Mg(II) favors dimer formation are in agreement with earlier reports [15], and suggest that interactions with His191 are critical for dimer stability (b) The imidazolium cation can compete with cationic side chains if a p–cation interaction is present at the dimer interface Recent analysis of dimeric interfaces has shown that p–cation interactions can make signifi-cant contributions to the binding energy for protein– protein complex formation, and it is suggested that such interactions be included in the list of criteria for characterizing protein interfaces [52] We examined the

Fig 8 Intersubunit interface hydrogen bond involving His191 in enolase crystal structures (A) Yen with two Mg(II) ions bound per subunit (Protein Data Bank: 1EBG) showing hydrogen bond between His191 and Gly15 (B) Yen with one Mg(II) ion bound per subunit (Protein Data Bank: 2ONE) has a hydrogen bond between His191 and Arg14 (C) Neuronal enolase in which two subunits are asymmetrically bound to one and two Mg(II) ions exhibits both types of hydrogen bond The subunit bound to one Mg(II) ion has a hydrogen bond between His189 and Arg14, and the other subunit, which is bound to two Mg(II) ions (Protein Data Bank: 1TE6), has a His189–Gly15 hydrogen bond (D) Rib-bon diagram of dimeric Yen (Protein Data Bank: 1EBG), in which yellow and blue represent two subunits Interface residues (Trp56 and Arg184) involved in p–cation interaction are shown in a stick representation.

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