Crystal Structure of α-D-Mannopyranosyl-(1→3)-β-D-mannopyranosyl-(1→4) -2-acetamido-2-deoxy-D-glucose

Warin, V.; Baert, F.; Fouret, R.; Strecker, Gérard; Spik, Geneviève; Fournet, Bernard; Montreuil, Jean

doi:10.1016/b978-0-12-301301-9.50066-9

Cited by 9 publications

(12 citation statements)

References 5 publications

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“…These minima are also consistent with previous calculations for this linkage that did not implicitly consider flexibility (26)(27)(28)(29). In two crystal structures of small molecules with this linkage this conformation is indeed found (20,30). However, in a complex between an oligosaccharide containing the linkage in I1 and a lectin, the Manp(p1-4)GlcpNAc linkage is found in a second minimum (3 1).…”

Section: Coi$ornzational Analysissupporting

confidence: 80%

“…Calculations were performed on a Microvax.) Briefly, they entail using the coordinates (X-ray) for these monosaccharides (20,21) as starting conformations. Then PE cubes were calculated using the program BIGTST using 60 6" increments for each of the torsion angles +,,, $,,, and w,, (i.e., sixty 60 X 60 PE surfaces).…”

Section: Methodsmentioning

confidence: 99%

“…Thus the rings were fixed at their geometries determined by X-ray diffraction of model compounds (20,21). This conformation is the 4~, chair conformation for both Manp and GlcpNAc and is supported by the observed coupling constants (see Experimental).…”

Section: Coi$ornzational Analysismentioning

confidence: 99%

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Syntheses of model oligosaccharides of biological significance. XII. Synthesis, NMR, and conformational analysis of trideuteriomethyl 4-O-(β-D-mannopyranosyl)- 2-acetamido-2-deoxy-β-D-glucopyranoside: the use of DEPT ¹H to ¹³C transfer for T₁ measurements and NOE assignments of tightly coupled ¹H nuclei

Lee¹,

Congson²,

Whitfield³

et al. 1992

Can. J. Chem.

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Ho HUAT LEE, LIGAYA N. CONGSON, DENNIS M. WHITFIELD, LAJOS R. RADICS, and JIRI J. KREPINSKY. Can. J. Chenl. 70, 2607 (1992).The title disaccharide Manp(p1-4)GlcpNAcpl-OCD, has been prepared by a short synthetic sequence through the inversion of configuration from gluco to marzrzo involving benzyl Glcp(p1-4)GlcpNAc. The disaccharide was subjected to detailed high-field 'H and I3c NMR study. First, conventional and 2D spectra were run to afford a co~nplete set of assigned spectral parameters. Next, steady-state 'H-{'H} NOE and 'H, ',c spin lattice relaxation experiments were performed to infer dynamic spectral data related to ~nolecular conformation. Owing to tight couplings and signal overlaps in the 'H spectrum, proton relaxation and selected NOE data were obtained via "C NMR after transfer of the actual, non-equilibrium, proton magnetization to the "C frequency domain. Using this experimental approach it has been found that T,'s for Manp H-4 and GlcpNAc H-2 were substantially longer than those of the other sugar ring protons, and that the principal interresidue dipolar contact in Manp(p 1 -4)GlcpNAcp 1 -OCD3 takes place between Manp H-l and

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Section: Coi$ornzational Analysissupporting

confidence: 80%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Syntheses of model oligosaccharides of biological significance. XII. Synthesis, NMR, and conformational analysis of trideuteriomethyl 4-O-(β-D-mannopyranosyl)- 2-acetamido-2-deoxy-β-D-glucopyranoside: the use of DEPT ¹H to ¹³C transfer for T₁ measurements and NOE assignments of tightly coupled ¹H nuclei

Lee¹,

Congson²,

Whitfield³

et al. 1992

Can. J. Chem.

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“…The conformation of the a-D-Man-(l+3)-j-~-Man bond (c'+d units) inferred from the N M R data and HSEA calculations is finally supported by a X-ray diffraction study of a trisaccharide, a-Man-( 1 +3)-f3-Man-(1+4)-j-GlcNAc [16] which reports values of -57.6", -19.4" and 48.0", S.O", respectively, for the values of &,$H for the two glycosidic linkages. These results agree well with the data for the same two glycosidic linkages (-50", -IS" and 5S", O", respectively) calculated using the HSEA program.…”

Section: Discussionmentioning

confidence: 88%

“…The coordinates for the units were available from neutron diffraction data of methyl 0-D-galactopyranoside (a units) [I31 and methyl a-D-mannopyranoside (c units) [I41 or from X-ray diffraction data of 2-acetamido-2-deoxy-/I-~-glucopyranose (b units) [I51 and P-D-mannopyranose (d units) [16]. In the last two cases the units were part of oligosaccharide structures, and the proton coordinates were generated on the heavy atoms as described previously [8].…”

Section: Hard-sphere Calculations and Molecular Plotsmentioning

confidence: 99%

The Preferred Conformation of Oligosaccharides Derived from the Complex‐Type Carbohydrate Portions of Glycoproteins

Bock¹,

Arnarp

Lōnngren

1982

European Journal of Biochemistry

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The preferred conformation in aqueous solution of oligosaccharides related to the complex-type carbohydrate portion of glycoproteins has been inferred from high-resolution nuclear magnetic resonance data (both ' H and I3C) combined with hard-sphere exo-anomeric calculations. The results indicate that the N-acetyl-lactosamine units are arranged in such a way that they are widely separated in space. Thus, these carbohydrates can cover large surface areas of the attached protein and provide good targets for recognition by other proteins.

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Relaxed potential energy surfaces of N‐linked oligosaccharides: The mannose‐α(1 → 3)‐mannose case

1990

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We report calculations of potential energy surfaces where all the internal coordinates of the disaccharide M a n 4 1 + 3)-Man-a-O-Me were relaxed and minimized through an extensive molecular mechanics scheme. Flexibility within the mannopyranose rings plays a crucial role. Introduction of the relaxed principle into the conformational description of the disaccharide does not greatly alter the overall shape of the low-energy domains but it reveals new local minima. However, its principle effect is the lowering of energy barriers in the potential energy surface. New conformational transitions about the glycosidic bonds appear, permiting pathways among the low energy sections. This occurs with only little variation of the classical 4C1 conformation of the mannopyranose residues. All the conformations observed in the solid state, along with those already predicted through the joint use of NMR and modeling techniques, fall into the populations of stable conformers calculated in the present work. Moreover, a satisfactory agreement is reached between previously observed NOE values, and the theoretical one, calculated from the averaging of more than 500 microstates. The present results reconciliate most of the apparently conflicting data previously reported; they provide strong support for the application of the concept of conformational averaging to solution behavior. Some limitations of the proposed methodology are also discussed.

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Crystal Structure of α-D-Mannopyranosyl-(1→3)-β-D-mannopyranosyl-(1→4) -2-acetamido-2-deoxy-D-glucose

Cited by 9 publications

References 5 publications

The Preferred Conformation of Oligosaccharides Derived from the Complex‐Type Carbohydrate Portions of Glycoproteins

Relaxed potential energy surfaces of N‐linked oligosaccharides: The mannose‐α(1 → 3)‐mannose case

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