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On the basis of the unique ability of squalene, the most hydrophobic purple membrane lipid, to induce recovery of M-fast activity in Triton-treated purple membrane, we proposed that this

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Purple membrane lipid control of bacteriorhodopsin conformational flexibility and photocycle activity

An infrared spectroscopic study

Richard W Hendler1, Steven M Barnett2, Swetlana Dracheva1, Salil Bose1and Ira W Levin2

1 Laboratory of Cell Biology, National Heart, Lung, and Blood Institute and 2 Laboratory of Chemical Physics,

National Institute of Diabetes and Digestive and Kidney Diseases, National Institutes of Health, Bethesda,

MD 20892-0510, USA

Specific lipids of the purple membrane of Halobacteria are

required for normal bacteriorhodopsin structure, function,

and photocycle kinetics [Hendler, R.W & Dracheva, S

(2001) Biochemistry (Moscow) 66, 1623–1627] The decay

of the M-fast intermediate through a path including the O

intermediate requires the presence of a hydrophobic

envi-ronment near four charged aspartic acid residues within the

cytoplasmic loop region of the protein (R W Hendler &

S Bose, unpublished results) On the basis of the unique

ability of squalene, the most hydrophobic purple membrane

lipid, to induce recovery of M-fast activity in Triton-treated

purple membrane, we proposed that this uncharged lipid

modulates an electrostatic repulsion between the membrane

surface of the inner trimer space and the nearby charged

aspartic acids of the cytoplasmic loop region to promote

transmembrane a-helical mobility with a concomitant increase in the speed of the photocycle We examined Triton-treated purple membranes in various stages of reconstitution with native lipid suspensions using infrared spectroscopic techniques We demonstrate a correlation between the vibrational half-width parameter of the protein a-helical amide I mode at 1660 cm)1, reflecting the motional char-acteristics of the transmembrane helices, and the lipid-induced recovery of native bacteriorhodopsin properties in terms of the visible absorbance maxima of ground state bacteriorhodopsin and the mean decay times of the photo-cycle M-state intermediates

Keywords: enzyme control; kinetics; lipid–protein inter-actions; membrane protein structure

Previous studies, summarized in [1], demonstrate the

importance of specific membrane lipids and amino-acid

residues in the cytoplasmic loop regions of

bacteriorhodo-psin for the normal operation of the bacteriorhodobacteriorhodo-psin

photocyle Specifically, the extensive damage to the normal

photocycle caused by brief exposure of purple membrane to

dilute Triton X-100 is repaired completely by the addition of

squalene and phosphatidylglycerophosphate methyl ester

lipids extracted from purple membrane [2] This

reconstitu-tion requires charge-screening by either high-salt

concen-trations or titration of a group with an apparent pK of 5

[3,4] Although phosphatidylglycerophosphate methyl ester

alone completely restores the M-slow (Ms) fi BR

photo-cycle pathway, squalene is required to re-establish the

M-fast (Mf) fi O fi BR pathway [2,5] The pK  5

titration implicates the involvement of peripheral acidic amino acids of bacteriorhodopsin near the membrane surface, namely, Asp36, Asp38, Asp102, and Asp104 within the cytoplasmic loop region (R W Hendler & S Bose, unpublished work) These observations indicate that Mf activity requires the site of the trimers to be in a membrane region containing squalene, the most hydrophobic lipid in the purple membrane, in close proximity to the four aspartates However, trimers located in a membrane region containing polar lipid in the absence of squalene produce

Msactivity This heterogeneous distribution of lipids within the membrane results in the formation of microdomains As the only difference between Mf- and Ms-eliciting trimers is the presence of a hydrophobic environment for the charged acidic amino acids, Msphotocycles can be converted into

Mfphotocycles by providing a hydrophobic environment (R W Hendler & S Bose, unpublished results)

On the basis of the above considerations, we proposed a mechanism for the control of bacteriorhodopsin photo-cycles through interactions involving squalene, charged lipids, and the four acidic amino acids in the cytoplasmic loop region (R W Hendler & S Bose, unpublished results) Thus, in the absence of squalene, electrostatic repulsive forces at the negatively charged membrane surface under the loop region containing the charged acidic amino acids should produce a strain limiting the mobility of both the amino-acid-containing loops and the attached transmem-brane a-helices These interactions would then lead to the

Correspondence to I W Levin, Laboratory of Chemical Physics,

National Institute of Diabetes and Digestive and Kidney Diseases,

National Institutes of Health, Bethesda, MD20892-0510, USA or

R W Hendler, Laboratory of Cell Biology, National Heart, Lung,

and Blood Institute.

Abbreviations: BR, ground state of bacteriorhodopsin; M f , M-fast

intermediate which decays through the O intermediate; M s , M-slow

intermediate which decays directly to bacteriorhodopsin.

(Received 13 September 2002, revised 20 January 2003,

accepted 22 January 2003)

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slower kinetic forms characteristic of the M state turnover.

To examine further these relationships, we investigated the

effects of purple membrane lipids on both the M turnover

time constants and the flexibility of the bacteriorhodopsin

transmembrane a-helices

Materials and methods

Purple membranes were extracted from the ET1001 strain

of Halobacterium salinarum as described previously [3]

Then 200 lL 1% Triton X-100 was added to a mixture of

100 lL purple membranes (5 mg bacteriorhodopsin per mL

suspension) and 1700 lL 50 mM potassium phosphate

(pH 7.2) The suspension was immediately centrifuged at

4C in a Beckman TL-100 centrifuge at 200 000 g (Triton

exposure time 7 min), and the pellet was washed three

times by resuspension in 3 mL water and centrifugation

Purple membrane lipids were extracted as described

previ-ously [6,7] and resuspended to a stock concentration of

4 mgÆmL)1 Reconstitution with lipid was performed by

mixing 10 mol of previously extracted native purple

mem-brane lipid per mol bacteriorhodopsin in the presence of

0–4MNaCl [3] This is the lipid concentration present in

native purple membrane As described previously [3], salt

was removed from the reconstituted preparation by

succes-sive centrifugations in dilute buffer Determinations of the

wavelength of maximum absorbance were performed on a

Cary 14DS spectrophotometer Kinetic bacteriorhodopsin

photocycle data, after an actinic light flash, were obtained

and analyzed as previously described [8,9]

Infrared spectroscopic measurements were obtained

through films cast at 35C on to a BaF2 window from

75 lL purple membrane suspension (5 mgÆmL)1)

Meas-urements were performed at 0.5 cm)1 resolution on a

Bomem DA3 spectrometer equipped with a mercury

cadmium telluride detector under either vacuum or a

nitrogen purge; spectra were similar for both instrumental

conditions Neutron scattering studies have demonstrated

that the average mean square displacements of molecular

vibrational modes in partially dried purple membrane films

are unchanged from fully hydrated systems [10] Direct

measurements [11] for the number of water molecules per

bacteriorhodopsin molecule in our preparations yielded

values close to 300, which is close to the value of 340

determined by neutron diffraction analysis [10] While other

low-frequency, anharmonic large-amplitude membrane

motions have been observed to precede the protein

conformational changes during the photocycle [12], the

behavior of various internal modes, such as the amide I and

amide II vibrations, provides a direct indication of the

dynamic properties of the transmembrane a-helices within

the bilayer assembly, as we have observed in

variable-temperature infrared-spectroscopic studies (unpublished

work) Vibrational spectroscopic bandwidths are functions

of dynamic parameters derived from intermolecular and

intramolecular motions Band shapes are often analyzed in

the context of statistical mechanical theories of irreversible

processes Interactive forces between the system and its

surrounding medium influence the vibrational relaxations of

the molecular assemblies under consideration The duration

of the re-equilibration processes that define the lifetimes of

the upper or excited vibrational levels leads to increments in

the observed bandwidths When molecules absorb radi-ation, band broadening occurs from the small differences in the environment that the molecular assembly encounters as

a consequence of its mobility; that is, the system experiences inhomogeneous broadening effects Additional discussion

of band profiles and reorientation effects can be found in references [13–15]

Spectral curve-fitting procedures Subtle protein motional changes, reflected specifically by perturbations in the amide I spectral region, are most easily and systematically monitored through curve-fitting methods applied to the 1720–1480 cm)1spectral interval, the region comprised primarily of the protein amide I and II vibrational modes Curve fitting of the infrared spectra of perturbed purple membrane assemblies was performed with a Bomem Grams/386 Briefly, the amide I and II envelope of the infrared spectrum of purple membrane assemblies was represented by seven curves initially located at 1660 cm)1 (representing the amide I modes of the a-helices), 1680 cm)1 (the amide I of b-turn structures), 1640 cm)1(the amide I of random coil and b-sheet structures), 1545 cm)1(the amide II

of a-helical A mode), and 1520 cm)1 (the amide II of a-helical E1 mode), with two smaller features at 1620 and

1585 cm)1 For all spectra fitted in this manner, the correlation coefficient was greater than 0.99, with the residuals being equivalent to the noise, indicating that these seven curves provide an excellent approximation to the data

Results

Effect of NaCl concentration on the reconstitution

of native purple membranes The extent of normal bacteriorhodopsin photocycle activity, generated in Triton-treated purple membranes by reconsti-tution with native phytanyl chain lipids, is dependent on NaCl concentration [3] As infrared spectroscopy provides

an effective approach for detailing changes in integral membrane protein structure [16,17] in both native and perturbed purple membrane systems [18], we examined the vibrational spectra of Triton-treated purple membranes reconstituted in various concentrations of NaCl (0–4M) to elucidate more specifically the protein structural changes that correlate with the recovery of native bacteriorhodopsin photocycle activity

The effect of NaCl concentration on structural reorgani-zations in the bacteriorhodopsin protein on reconstitution

of Triton-treated purple membrane with native lipids was monitored through changes in infrared spectra in the amide I and II regions at 1660 cm)1and  1545 cm)1, respectively Figure 1 displays the infrared spectra from

1710 to 1490 cm)1 (normalized to the intensity of the amide I mode at 1660 cm)1) of native purple membrane (solid line), purple membrane after mild exposure to Triton (0.1% Triton, 7 min; dashed line), and Triton-treated purple membrane reconstituted in the absence of NaCl (dotted line) and with 2MNaCl in phosphate buffer (dash-dot line) The decrease in half-width of the amide I mode at

1660 cm)1 after exposure to Triton suggests decreased a-helical conformational flexibility (bacteriorhodopsin is

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composed of 65% a-helical structure [18]); that is, the

amide I mode monitors primarily the dynamics of the

protein’s transmembrane segments in contrast with the loop

regions Increases in the width of the amide I mode are

observed in variable-temperature infrared spectroscopic

studies of the purple membrane system (unpublished

observations) In these studies, however, a decrease in peak

width of the amide I vibrational mode is accompanied by a

decrease in the intensity and bandwidth of the amide II

mode on the release of retinal induced by either heat or light

(S Barnett & I W Levin, unpublished work) These small

decreases in the amide I and amide II peak parameters were

observed in the present study and in previous

communica-tions [19,20] on lipid reconstitution in the absence of NaCl

(Fig 1, dotted line) Recovery of these parameters to levels

near those observed in native purple membrane are now

observed on reconstitution in 2MNaCl (Fig 1, dash-dot

line)

Examination of the lineshape features of an

infrared-active spectroscopic feature, such as the peak heights and

bandwidths, provides insights into the molecular dynamics

of the ensemble [21] In particular, to define more explicitly

the structural alterations in bacteriorhodopsin after

expo-sure to Triton and subsequent lipid reconstitution, the

amide I and II regions of the infrared spectra in both the

native and perturbed purple membrane systems were fitted

to seven mixed Gaussian–Lorentian functions Figure 2

displays the infrared spectrum of native purple membrane

from 1720 to 1480 cm)1 (top curve) fitted to the seven

deconvoluted curves The amide I region is composed of a

predominant feature centered at 1660.3 cm)1with a

half-width (Dm1/2) of 30.9 ± 0.5 cm)1(mean ± SEM from at

least eight independent measurements used on all native and

treated purple membrane preparations), assigned to the

a-helices of bacteriorhodopsin, as well as, in part, curves

typical of b-turn (1685 cm)1) and either random coil or

b-sheet (1638 cm)1) structures The frequencies and relative

intensities of the spectroscopic features that comprise the

amide I region predict that bacteriorhodopsin is composed

of  65% a-helical structure, in agreement with previous

infrared spectroscopic studies of bacteriorhodopsin secon-dary structure [18]; the curves displayed in Fig 2 represent the only combination that provided an a-helical composi-tion of greater than 50% Table 1 lists the deconvoluted full width at half heights of the a-helical amide I mode at

Fig 1 Infrared spectra from 1710 to

1490 cm-1of native purple membrane (solid line), purple membrane exposed briefly to Triton (dashed line), and purple membrane reconstituted with purple membrane lipids in solutions without NaCl (dotted line) and with

2 M (dot-dash line) NaCl.

Fig 2 Infrared spectrum of native purple membrane from 1720 to

1480 cm-1(top curve) and the seven mixed Gaussian–Lorentzian curves used to fit this spectral region.

Table 1 Full width at half height of the a-helical amide I modes at

1660 cm -1 (Dm 1/2 ; obtained from deconvoluted spectra; ± 0.5 cm -1 ) for different lipid conditions.

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1660 cm)1 (Dm1/2) for all samples in this study We

emphasize the use of this parameter as a measure of

bacteriorhodopsin a-helical conformational flexibility,

because the 1660 cm)1feature arises predominantly from

a-helical structures [18]

The experimentally observed half-width of the entire

envelope comprising the amide I modes in the infrared

spectra of the purple membrane decreases 9% (from 48.4

to 44 cm)1) on brief exposure to Triton [19] The

curve-fitting procedure used here permits a more accurate

evaluation of the specific structural elements affected by

Triton exposure A decrease in intensity of the features

corresponding to the b-turn (1685 cm)1) and random coil/

b-sheet (1638 cm)1) structures is accompanied by an 8%

decrease in Dm1/2(from 30.9 to 28.5 cm)1; ± 0.5 cm)1) on

exposure to Triton The recovery of Dm1/2to values observed

in native purple membrane on lipid reconstitution into

Triton-treated purple membrane occurs as a function of

NaCl concentration used during the procedure Figure 3

displays a plot of Dm1/2 as a function of the NaCl

concentrations used for reconstitution Reconstitution of

Triton-exposed membranes with purple membrane lipids

shows a strong dependence on the concentration of NaCl

such that, at the highest concentration, the half-width

parameter was restored to a value close to that found in

native purple membranes, accompanied by a recovery in the

b-turn and random coil/b-sheet regions The observed

decrease in Dm1/2on exposure to Triton [19], and its recovery

on lipid reconstitution in high-saline medium (Fig 3 and

Table 1) presents an opportunity to correlate the structural

features altered on lipid perturbation with

bacteriorhodop-sin photocycle activity after exposure to Triton

Correlations between the recovery of bacteriorhodopsin

photocycle parameters and Dm1/2

Infrared spectra and bacteriorhodopsin kinetic data were

obtained on samples immediately after lipid reconstitution

and removal of salt Correlations between lipid-sensitive

bacteriorhodopsin photocycle parameters and Dm were

performed after reconstitution in the presence of up to 4M NaCl Specific parameters describing bacteriorhodopsin structure and photocycle behavior, as noted below, correlate well (compare Figures 3–5) with the recovery of Dm1/2 in the infrared spectra of reconstituted purple membrane assemblies; other parameters (see below) displayed little or

no correlation

The wavelength of maximum absorbance (kmax) of protonated retinal Schiff base analogs in solution is

446 nm [22] Chromophore distortions induced by the surrounding protein surface shift kmaxto 569 nm in native purple membrane [23] Exposure to Triton decreases kmaxto

 562 nm [24]; lipid reconstitution in 1M NaCl restores

kmaxto 566 nm, while in higher NaCl concentrations, this parameter returns to native-like values [3] Figure 4 displays

a plot of k vs Dm for Triton-treated purple membrane

Fig 3 Plot of the half-width of the a-helical amide I mode (Dm 1/2 ) vs.

NaCl concentration used for reconstitution The line drawn is the result

of a second order polynomial fit.

Fig 4 Plot of the wavelength of maximum absorbance for light-adapted purple membrane (k max ) vs the half-width of the a-helical component of the amide I mode (Dm 1/2 ) in bacteriorhodopsin for purple membrane systems reconstituted in the absence of NaCl (Dm 1/2 = 29.2 cm)1) and

in 0.5 M NaCl (Dm 1/2 = 29.6 cm)1), 1 M NaCl (Dm 1/2 = 30.4 cm)1) and 2 M NaCl (Dm 1/2 = 30.8 cm)1).

Fig 5 Plot of the mean M intermediate decay time (j) vs the half-width of the a-helical component of the amide I mode (Dm 1/2 ) in bacte-riorhodopsin.

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systems reconstituted with native lipids at various NaCl

concentrations The shift in kmaxon lipid perturbation by

Triton originates from twists in the retinal structure

and changes in its environment induced by a

bacteriorho-dopsin conformational change, which produces altered

protein–retinal interactions [25], while the decrease in Dm1/2

arises from decreased mobility of the bacteriorhodopsin

a-helix structures The linear correlation between the two

parameters demonstrates complete recovery to 569 nm as

Dm1/2recovers to 30.5 cm)1, approximately the half-width

observed in native purple membrane

The recovery of normal bacteriorhodopsin photocycle

behavior may also be correlated with Dm1/2 for kinetic

parameters that describe the decay of

bacteriorhodop-sin intermediates The average decay time s of the M410

intermediate is an important diagnostic parameter It is the

weighted average of time constants for all forms of M present

and is influenced by the mix of M-fast and M-slow cycles A

low value results from a preponderance of M-fast cycles,

whereas a high value results from a paucity of M-fast cycles

In native purple membrane, the average s is 4 ms, arising

from the mix of rapidly decaying species (Mf) with a decay

time of 2 ms and the slower component (Ms) with a decay

time of 6 ms Exposure to Triton increases the average s to

 70 ms through loss of the Mf decay pathway and the

generation of new, longer-lived M intermediates (R W

Hendler & S Bose, unpublished work) Reconstitution in

1M NaCl partially recovers the Mf pathway and lowers

average s to 19 ms, while average s decreases to less than

5 ms on full reconstitution in high saline medium [3]

Figure 5 displays a plot relating s with Dm1/2 for the

reconstituted purple membrane systems A linear correlation

between Dm1/2and the average M decay time occurs over a

wide range of decay times, illustrating that the

conforma-tional flexibility described by Dm1/2 provides a faithful

description of the dynamics of the transmembrane helical

segments that relate to M intermediate decay during the

bacteriorhodopsin photocycle

The number of bacteriorhodopsin molecules that

under-go a photocycle after a brief, high-intensity flash, termed the

bacteriorhodopsin turnover, is greatly diminished after

Triton exposure, reflecting the decreased ability of actinic

light to initiate the bacteriorhodopsin photocycle in the

perturbed systems [3] This turnover may be quantified by

either the maximum decrease in absorbance at 569 nm or

increased absorbance at 410 nm (representing the M410

formed) during the photocycle Specifically, native purple

membrane exhibits a change in absorbance at 569 nm of

 100 milli-absorbance units for specific conditions

des-cribed previously [3] On exposure to Triton, decreased

bacteriorhodopsin turnover results in a decreased change in

absorbance of only 66 milli-absorbance units, because fewer

bacteriorhodopsin molecules undergo a photocycle for the

same conditions On reconstitution in high-saline medium,

the bacteriorhodopsin turnover returns to native-like values

as quantified by the return to native values in the

absorbance loss at 569 nm during the photocycle Figure 6

presents the maximum loss in absorbance at 569 nm during

the photocycle as a function of Dm1/2 for the purple

membrane systems The nonlinear recovery of the

bacte-riorhodopsin turnover with Dm1/2 indicates that the

struc-tural features that govern bacteriorhodopsin turnover rate

involve other considerations than just the mobility of the a-helices

Discussion

The data presented here demonstrate definitive correlations between the presence of native purple membrane lipid, the time constants for M-turnover, and the mobility, or motional characteristics, of the bacteriorhodopsin trans-membrane a-helices We emphasize the ability of infrared spectroscopy to reflect the a-helical conformational flexibi-lity of bacteriorhodopsin in native purple membranes after depletion of lipids by Triton exposure and subsequent stepwise reconstitution in lipid dispersions containing vari-ous concentrations of NaCl which control the extent of lipid rebinding The intrinsic mobility of the transmembrane a-helices of bacteriorhodopsin in purple membranes is related specifically to the deconvoluted widths of the a-helical amide I mode Dm1/2at 1660 cm)1 On exposure

to 0.1% Triton X-100, Dm1/2 decreases, accompanied by some disruption in the well-ordered purple membrane lattice Although lipid reconstitution in the absence of NaCl recovers some of the structural parameters affected by Triton exposure [3,19], the presence of NaCl is required for

a complete, functionally active system, as demonstrated by correlations between the recovery of specific kinetic bacte-riorhodopsin photocycle parameters and changes in Dm1/2 (Figs 3–5)

Roles of squalene and polar lipid in bacteriorhodopsin function

The correlation between the extent of reconstitution with purple membrane lipid (i.e squalene) and the degree of the

Mf fi O fi BR photocycle activity and a-helical flexi-ble mobility supports the proposal for bacteriorhodopsin photocycle control being shared among squalene, polar lipids, and acidic amino acids of the cytoplasmic loop region An extension of this concept accounts for all four

Fig 6 Plot of the absorbance change at 569 nm in photoexcitation (DmOD) vs the half-width of the a-helical component of the amide I mode (Dm 1/2 ) in bacteriorhodopsin The line drawn is the result of a third-order polynomial fit.

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distinct kinetic forms of M present in purple membrane

(R W Hendler & S Bose, unpublished results) If we

attribute the four kinetic forms to different amounts of

modulation of charge repulsion by squalene, the simplest

model requires zero, one, two, or three squalenes per

monomer As shown in Table 2, for 10 molecules of

wild-type bacteriorhodopsin, this requires three squalenes for

each of the four molecules displaying Mfactivity and two

squalenes for each of the six molecules displaying Ms

activity, yielding a squalene/bacteriorhodopsin ratio of

24 : 10 Similarly, to account for the three forms of

bacteriorhodopsin found in a the Triton-treated case listed

in Table 2, the ratio would be 5 : 10 Recent

redetermina-tions of squalene/bacteriorhodopsin stoichiometries in

native purple membrane using NMR procedures raise the

originally determined value of 1–2, a value closer to that

for the control shown in Table 2 [26]

The type of interaction described in R W Hendler &

S Bose (unpublished results) here between a membrane

lipid and specific amino-acid residues of an active integral

protein such as to influence and control the structure and

function of the protein may be a prototype for similar

interactions in other membrane-protein systems

References

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Table 2 Model for squalene regulation of M-turnover The values in

parentheses are the number of squalenes per bacteriorhodopsin for the

kinetic species of M SQ, Squalene; BR, bacteriorhodopsin.

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