The crystal structure of triacetylsphingosine

O'Connell, A. M.; Pascher, I.

doi:10.1107/s0567740869006078

Cited by 26 publications

(5 citation statements)

References 4 publications

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“…The dimensions of the acetylamino group are in general agreement with those in similar structures, e.g. in triacetylsphingosine (O'Connell & Pascher, 1969); N-acetylglycine (Donohue & Marsh, 1962); and N-acetyl-~-D-glucosamine (Johnson, 1966). The five C-OH type bonds have an average length of 1-421 A.…”

Section: Discussionsupporting

confidence: 83%

The crystal structure of N-acetylneuraminic acid methyl ester monohydrate

O'Connell¹

1973

Acta Crystallogr Sect B

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The crystal structure of the methyl ester of N-acetylneuraminic acid monohydrate has been determined from three-dimensional X-ray diffraction data. The crystals are orthorhombic, space group P212121, with unit-cell constants a=7.954+ 1, b= 11.675+4, c= 16.974+2 ~. The structure was solved using the tangent formula and refined by block-diagonal least-squares techniques to R=0.042. The three bulky substituent groups, the N-acetyl, the glycero and the methyl ester groups, are all equatorially bonded to the pyranose ring while the hydroxyl group at the anomeric carbon atom C(2) is in the axial position. An extensive system of seven inter-and one intramolecular hydrogen bonds holds the molecules quite rigidly in the crystal lattice, resulting in an average overall isotropic temperature factor coefficient of only 2.7 ,~2.

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Section: Discussionsupporting

confidence: 83%

The crystal structure of N-acetylneuraminic acid methyl ester monohydrate

O'Connell¹

1973

Acta Crystallogr Sect B

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“…1.521 (3) C(9)--C(10)-C(11) 114.3 (2) C(11)- C(12) 1.502 (4) C(10)-C(11)-C(12) 112-9 (2) (2) The mean C(sp3)-C(sp 3) bond distance is 1.512 (4) A and the mean C-C-C angle for the same carbon atoms is 113.9 (2) ° (see, however, below). These values are in agreement with those found in other long hydrccarbon chains (Jensen & Mabis, 1966;O'Connell, 1968;O'Connell & Pascher, 1969). The systematically short bond lengths and large bond angles are most probably due to thermal motion and rotatory oscillations of the chain around the long axis.…”

Section: Internationai Tablesforx-raycrystallographyi(1962)for Ment Asupporting

confidence: 91%

The crystal structure of 13-oxoisostearic acid

Dahlén¹

1972

Acta Crystallogr Sect B

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13-Oxoisostearic acid (16-methyl-13-oxoheptadecanoic acid) is triclinic (PT) with a=4"933, b= 5.623, e=34"460 ~, ~=95.65, //=94.01 and y=103"60 °. The molecules are arranged in hydrogen-bonded dimers in which the chain axes are tilted 44 ° to the end-group planes to allow the methyl branches to be accommodated between the methyl ends of the chains. The keto oxygen is directly incorporated into the chain packing with a resulting strain at the sp 2 carbon atom. This leads to a bend of the chain axis in the zigzag plane of the molecule. The carboxyl group forms an angle of 13 ° with the chain plane.

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“…For example, crystal structures of fatty acids (for a review, see ref. 7), glycerol (8), and sphingosine derivatives (9) have been reported. Also various substituted aminophosphates (10)(11)(12), including glycerylphosphorylethanolAbbreviation: Phosphatidylethanolamine, 1,2 dilauroyl-DL-phosphatidylethanolamine.…”

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Structural Chemistry of 1,2 Dilauroyl-DL-phosphatidylethanolamine: Molecular Conformation and Intermolecular Packing of Phospholipids

Hitchcock

Mason

Thomas

et al. 1974

Proc. Natl. Acad. Sci. U.S.A.

355

230

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Crystals of 1,2 dilauroyl-DL-phosphatidylethanolamine: acetic acid are monoclinic with a = 46.2, b = 7.77, c = 9.95 A, j3 = 92.00; space group P21/c. The structural analysis, based on the visual estimates of 1467 reflection intensities, was achieved by direct methods, and least squares analysis convergence was to R1 = 0.28. There are marked differences between the observed molecular conformation and those that have been predicted theoretically. The mean planes containing the lipid chains are essentially parallel to one another; the phosphodiester moiety has a double gauche conformation, while intermolecular hydrogen bonding modifies the conformation that could be anticipated for an isolated phosphatidylethanolamine molecule. The intermolecular packing produces the classical lipid bilayer structure, adjacent lipid bilayers being separated by acetic acid molecules of crystallization. The hydrocarbon chain packing can be considered either as a quasi-hexagonal type or as a complex orthorhombic subcell arrangement. One-dimensional electron density profiles across the lipid bilayer at increasing resolution clearly demonstrate the origin of features present on the low resolution profiles of both model and natural membranes.Phospholipids, glycolipids, and glycosphingolipids play a key structural and functional role in animal, plant, and bacterial cell membranes (1). Furthermore, phospholipids are important molecular components of the serum lipoproteins responsible for fat transport in the body (2) and of bile secreted by the liver where, together with bile salts, they solubilize cholesterol in a complex, aqueous, mixed micellar system (3).Although much information is available on the behavior of phospholipids in water (4, 5), the mutual interactions of different lipid classes, particularly phospholipid-cholesterol (6) (14), and sugars (15), which determine the different lipid classes, have been described. From this structural information, conformational analyses of different phospholipids have been made and, on this basis, the most likely structures have been predicted (12,16,17).In this paper we describe a single-crystal analysis of a phospholipid, the synthetic compound 1,2 dilauroyl-DL-z HsOJI-OCHsCHr-NHa O_ A knowledge of the molecular conformation and intermolecular packing of phosphatidylethanolamine and other phospholipids will allow a more detailed interpretation of the x-ray diffraction data derived from lipid-water, lipid-protein, and natural membrane systems.

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The crystal structure of triacetylsphingosine

Cited by 26 publications

References 4 publications

The crystal structure of N-acetylneuraminic acid methyl ester monohydrate

The crystal structure of N-acetylneuraminic acid methyl ester monohydrate

The crystal structure of 13-oxoisostearic acid

Structural Chemistry of 1,2 Dilauroyl-DL-phosphatidylethanolamine: Molecular Conformation and Intermolecular Packing of Phospholipids

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