Crystal structures of membrane lipids

Pascher, I.; Lundmark, M.; Nyholm, Per-Georg; Sundell, Staffan

doi:10.1016/0304-4157(92)90006-v

Cited by 229 publications

(222 citation statements)

References 77 publications

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“…This is further strengthened by the observation of bilayer arrangement in both the polymorphic forms of NPEA. Because intermolecular hydrogen bonds between the head groups of neighboring molecules are found in the crystal structures of phosphatidylethanolamines (43,44) as well as in all of the NAEs for which crystal structures are known, namely NMEA (29), NSEA (35), and NPEA (this study), it appears likely that hydrogen bond formation between phosphatidylethanolamine and NAE may play an important role in such stabilization. Currently, we are investigating the mixing properties of NAEs and phosphatidylethanolamines to understand their interaction at the molecular level.…”

Section: Dscmentioning

confidence: 71%

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Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist

Kamlekar

Swamy

2006

Journal of Lipid Research

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The molecular structure, packing properties, and intermolecular interactions of two structural polymorphs of N-palmitoylethanolamine (NPEA) have been determined by single-crystal X-ray diffraction. Polymorphs a and b crystallized in monoclinic space group P 2 1 /c and orthorhombic space group P bca, respectively. In both polymorphs, NPEA molecules are organized in a tail-to-tail manner, resembling a bilayer membrane. Although the molecular packing in polymorph a is similar to that in N-myristoylethanolamine and N-stearoylethanolamine, polymorph b is a new form. The acyl chains in both polymorphs are tilted by z35°with respect to the bilayer normal, with their hydrocarbon moieties packed in an orthorhombic subcell. In both structures, the hydroxy group of NPEA forms two hydrogen bonds with the hydroxy groups of molecules in the opposite leaflet, resulting in extended, zig-zag type H-bonded networks along the b-axis in polymorph a and along the a-axis in polymorph b. Additionally, the amide N-H and carbonyl groups of adjacent molecules are involved in N-HÁÁÁO hydrogen bonds that connect adjacent molecules along the baxis and a-axis, respectively, in a and b. Whereas in polymorph a the L-shaped NPEA molecules in opposite layers are arranged to yield a Z-like organization, in polymorph b one of the two NPEA molecules is rotated 180°, leading to a W-like arrangement. Lattice energy calculations indicate that polymorph a is more stable than polymorph b by z2.65 kcal/ mol.-Kamlekar, R. K. and M. J. Swamy. Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist.

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Section: Dscmentioning

confidence: 71%

“…in the P bnm space group. The unit cell dimensions of these subcells are as follows: a Crystal structures of N-palmitoylethanolamine polymorphstwo molecules are attributable to the very high tilt angle of the acyl chains with respect to the bilayer normal (43)(44)(45).…”

Section: Subcell Structurementioning

confidence: 99%

Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist

Kamlekar

Swamy

2006

Journal of Lipid Research

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“…Fluid bilayers are biologically relevant because cellular membranes must be in a £uid state for cells to function. But, their high thermal disorder excludes completely the possibility of atomic-resolution three-dimensional crystallographic images that can be obtained from crystallized membrane lipids [48,49]. Multilamellar bilayers obtained from phospholipids by dispersal in water or deposition on surfaces, liquid crystals, are highly periodic in a direction normal to the bilayers, but highly thermally disordered in the bilayer plane.…”

Section: Structural and Chemical Features Of The Bilayer Interfacementioning

confidence: 99%

Hydrophobic interactions of peptides with membrane interfaces

White

Wimley

1998

Biochimica et Biophysica Acta (BBA) - Reviews on Biomembranes

513

462

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The thermodynamic principles underlying the structural stability of membrane proteins are difficult to obtain directly from whole proteins because of intractable problems related to insolubility in the aqueous phase and extreme stability in the membrane phase. The principles must therefore be surmised from studies of the interactions of small peptides with lipid bilayers. This review is concerned with the hydrophobic interactions of such peptides with the interfacial regions of lipid bilayers. We first develop a general framework for thinking about the thermodynamics of membrane protein stability that centers on interfacial interactions and review the structural and chemical evidence that supports this interface-centered point of view. We then describe an experimentally determined whole-residue interfacial hydrophobicity scale that reveals the central role of the peptide bond in partitioning and folding. Finally, we consider the complexity and diversity of interfacial interactions revealed by differences between side-chain hydrophobicities determined using different classes of peptides. ß 1998 Elsevier Science B.V. All rights reserved.

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“…1 These lipids were semisynthesized in this laboratory; however, they all resemble strictly the naturally occurring monoenoic phosphatidylcholines. The structures of these cis-monoenoic phosphatidylcholines were simulated using the molecular mechanics method, specifically the MM3(92) force field (5).…”

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confidence: 99%

Phosphatidylcholines with sn-−1 Saturated and sn-−2 cis-Monounsaturated Acyl Chains

Wang

Huo

et al. 1995

Journal of Biological Chemistry

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Recently, we have shown by high resolution differential scanning calorimetry that the position of a cis double bond (⌬-bond) in a series of 1-stearoyl-2-octadecenoyl-phosphatidylcholines can affect the phase transition temperature (T m ) or enthalpy (⌬H) of the gelto-liquid crystalline phase transition of this series of lipids in the following manner. The value of T m (or ⌬H) is minimal when the ⌬-bond is positioned at C(11) in the sn-2 acyl chain; in addition, this value increases steadily as the ⌬-bond migrates toward either end of the acyl chain, resulting in a symmetrical, inverted bell-shaped profile (Wang, Z.-q., Lin, H.-n., Li, S., and Huang, C. (1995) J. Biol. Chem. 270, 2014 -2023). In this communication, we have further demonstrated the inverted bell-shaped profile of T m using 1-arachidoyl-2-eicosenoyl-phosphatidylcholines. In addition, we have extended the lipid series of 1-stearoyl-2-octadecenoyl-phosphatidylcholines to include 1-arachidoyl-2-octadecenoyl-phosphatidylcholines and 1-behenoyl-2-octadecenoyl-phosphatidylcholine, each series with a ⌬-bond at varying carbon position of 6, 7, 9, 11, 12, and 13. Calorimetric results obtained with these three series of lipids indicate that the inverted bell-shaped curve shifts toward higher temperatures in a nonuniform manner as the saturated sn-1 acyl chain length increases from 17 to 19 and then to 21 C-C bond lengths. Specifically, the T m (or ⌬H) values are nearly identical for these cis-monoenoic lipids when their ⌬-bonds are positioned at C(13). Based on the height of the rotational energy barrier obtained with molecular mechanics calculations, it is evident that the rotational flexibility of the single C-C bond adjacent to the ⌬-bond in 1-stearoyl-2-octadecenoyl-phosphatidylcholine increases as the ⌬-bond migrates from C(9) to C(13). The differential scanning calorimetry results obtained with the three series of lipids can thus be attributed to an increase in the rotational flexibility of the short chain segment succeeding the C(14) atom in the sn-2 octadecenoyl chain. In this communication, we also propose that in the gel-state bilayer of sn-1 saturated/ sn-2 cis-monounsaturated phosphatidylcholine the entire length of the shorter segment of the sn-2 acyl chain acts as a structural perturbing element; hence, it is mainly responsible for the large lower T m of the monoenoic lipid relative to the saturated counterpart. Finally, two general equations relating T m with the structural parameters of cis-monoenoic phosphatidylcholines are presented. These equations, formulated primarily on the assumption that the short segment of the sn-2 acyl chain acts as a perturbing element, are shown to have strong predictive power in estimating the T m values of the gel-to-liquid crystalline phase transitions for sn-1 saturated/sn-2 cis-monounsaturated phosphatidylcholines.Phosphatidylcholines isolated from the plasma membrane of eukaryotic cells are a structurally diverse group of phospholipids. The bewildering variety of membrane phosphatidylcholines originates fro...

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Crystal structures of membrane lipids

Cited by 229 publications

References 77 publications

Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist

Molecular packing and intermolecular interactions in two structural polymorphs of N-palmitoylethanolamine, a type 2 cannabinoid receptor agonist

Hydrophobic interactions of peptides with membrane interfaces

Phosphatidylcholines with sn-−1 Saturated and sn-−2 cis-Monounsaturated Acyl Chains

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