Structure cristalline de la 2-acétamido-1-N-(l-aspart-4-oyl)-2-désoxy-β-d-glucopyranosylamine

Ohanessian, J.; Avenel, D.; Neuman, A.; Gillier‐Pandraud, H.

doi:10.1016/s0008-6215(00)85309-4

Cited by 26 publications

(25 citation statements)

References 23 publications

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“…Selected list of bond lengths and bond angles is provided in Table 1. Comparison of pyranose ring C-O bond lengths shows that C1-O5 bond length is shorter than the C5-O5, which was also observed in other β-1-N-alkanamido sugar derivatives including GlcNAcβAsn [3] & GlcβAsn [15]. The C1-N1 and C3-N3 bond distances are in the range of 1.41-1.45Å.…”

Section: Structure Descriptionmentioning

confidence: 55%

“…Synthesis of N-(3-deoxy-3-acetamido-β-D-glucopyranosyl) alkanamides (3)(4) The N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)alkanamides, 3-4, were planned to be synthesized starting from the commercially available 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose. The reported literature procedure [9] was employed for converting 1,2:5,6-di-O-isopropylidene-α-Dglucofuranose to the C3 azido sugar (5) (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

“…The = N values of 3 and 4 are comparable and taken together with the ϕ N values reveal the Z-anti conformation of the amide aglycon moiety. The Z-anti conformation of the amide linkage has been observed in 1, 2 and GlcNAcβAsn [3].…”

Section: Linkage Region Conformationmentioning

confidence: 95%

“…A systematic X-ray crystallographic study of models GlcNAcβAsn [3] and GlcNAcβNHAc(1) [4] (Fig. 2) of the N-glycoprotein linkage region and many of their analogs has shown that the key torsion, ϕ N , is influenced to a greater extent by the structural variation of the glycan part than that of the aglycon group [5].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and X-ray crystallographic investigation of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)alkanamides as analogs of N-glycoprotein linkage region

2011

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As part of our ongoing program aimed at understanding the structural significance of GlcNAcβAsn linkage conserved in all eukaryotic N-glycoproteins, the present study reports on the synthesis and X-ray crystal structures of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)acetamide (Glc3NAcβNHAc) and the corresponding propionamide (Glc3NAcβNHPr). Comparative analysis of these structures with those of the corresponding GlcNAc (C2 acetamido) compounds showed that the bifurcated anti-parallel pattern involving N-H…O and C-H…O hydrogen bonds, the hallmark feature of the N-glycoprotein models, GlcNAcβNHAc and GlcNAcβAsn, is absent in both the C3 acetamido analogs. The extended (anti) conformation of the amido aglycon moiety as defined by χ(2) seen in the case of C2 acetamido derivative, GlcNAcβNHPr, turns into gauche for the C3 acetamido analog (Glc3NAcβNHPr). This observation is consistent with the earlier work on the critical role of the C2-NHAc group of GlcNAcβAsn in controlling χ(2) at the linkage region of N-glycoproteins.

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Section: Structure Descriptionmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Section: Linkage Region Conformationmentioning

confidence: 95%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and X-ray crystallographic investigation of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)alkanamides as analogs of N-glycoprotein linkage region

2011

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“…14 The latter angle is found to be consistently smaller than the former, and this is attributed to the effect of the lone pair of electrons causing a bend at the oxygen on the O5-C5-C6 bond angle. Such a difference in these bond angles has been observed in the crystal structures of GlcNAcbAsn 15 and several N-linked pyranoses. 16 The N-glycosidic valence angle, O5-C1-N1, is smaller than that of C2-C1-N1 for 3 and the same trend is consistently seen in analog 6.…”

Section: Crystal Structure Of Glcnacbnhbu (3) and (Glcnacb(1-4)glcnacmentioning

confidence: 59%

Synthesis and X-ray crystallographic investigation of N-(β-d-glycosyl)butanamides derived from GlcNAc and chitobiose as analogs of the conserved chitobiosylasparagine linkage of N-glycoproteins

Mathiselvam

Srivastava

Varghese

et al. 2013

Carbohydrate Research

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Crystal structure and solution conformation of 1‐N‐acetyl‐β‐D‐glucopyranosyl amine: A model for the glycopeptide linkage

1982

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SynopsisThe crystal structure of the title compound, a model for the glycosyl linkage between the asparagine side chain and N-acetyl glucosamine in glycoproteins, has been determined and compared to other model structures. The pyranose ring in the crystal is in the 4C1 chair conformation and the amide functions at C1 and at Cz are both oriented such that the amide protons are nearly trans to their respective sugar-ring protons. Coupling constants determined from the fully assigned proton nmr spectrum in aqueous solution are consistent with the conformation in the crystal.

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Structure cristalline de la 2-acétamido-1-N-(l-aspart-4-oyl)-2-désoxy-β-d-glucopyranosylamine

Cited by 26 publications

References 23 publications

Synthesis and X-ray crystallographic investigation of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)alkanamides as analogs of N-glycoprotein linkage region

Synthesis and X-ray crystallographic investigation of N-(3-deoxy-3-acetamido-β-D-glycopyranosyl)alkanamides as analogs of N-glycoprotein linkage region

Synthesis and X-ray crystallographic investigation of N-(β-d-glycosyl)butanamides derived from GlcNAc and chitobiose as analogs of the conserved chitobiosylasparagine linkage of N-glycoproteins

Crystal structure and solution conformation of 1‐N‐acetyl‐β‐D‐glucopyranosyl amine: A model for the glycopeptide linkage

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