1210451-90-3

Basic information

• Product Name: N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)methanesulfonamide
• Synonyms: N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)methanesulfonamide
• CAS NO: 1210451-90-3
• Molecular Weight: 425.414
• Mol File: 1210451-90-3.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)methanesulfonamide(CAS DataBase Reference)
• NIST Chemistry Reference: N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)methanesulfonamide(1210451-90-3)
• EPA Substance Registry System: N-(2,3,4,6-tetra-O-acetyl-β-D-mannopyranosyl)methanesulfonamide(1210451-90-3)

Safety Data

• Hazardous Substances Data: 1210451-90-3(Hazardous Substances Data)

Upstream product

• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 

Relevant articles and documents

Exploring the effect of bioisosteric replacement of carboxamide by a sulfonamide moiety on N-glycosidic torsions and molecular assembly: Synthesis and x-ray crystallographic investigation of n-(β- D -glycosyl)sulfonamides as n-glycoprotein linkage region analogues

N-Glycoprotein linkage region constituents, 2-acetamido-2-deoxy-β-D- glucopyranose (GlcNAc) and asparagine (Asn) are conserved among all the eukaryotes. To gain a better understanding for nature's choice of GlcNAcβAsn as linkage region constituents and inter- and intramolecular carbohydrate-protein interactions, a detailed systemic structural study of the linkage region conformation is essential. Earlier crystallographic studies of several N-(β-glycopyranosyl)alkanamides showed that N-glycosidic torsion, φN, is influenced to a larger extent by structural variation in the sugar part than that of the aglycon moiety. To explore the effect of the bioisosteric replacement of a carboxamide group by a sulfonamide moiety on the N-glycosidic torsions as well as on molecular assembly, several glycosyl methanesulfonamides and glycosyl chloromethanesulfonamides were synthesized as analogues of the N-glycoprotein linkage region, and crystal structures of seven of these compounds have been solved. A comparative analysis of this series of crystal structures as well as with those of the corresponding alkanamido derivatives revealed that N-glycosidic torsion, φN, does not alter significantly. Methanesulfonamido and chloromethanesulfonamido derivatives of GlcNAc display a different aglycon conformation compared to other sulfonamido analogues. This may be due to the cumulative effect of the direct hydrogen bonding between N1 and O1′ and C-H×××O interactions of the aglycon chain, revealing the uniqueness of the GlcNAc as the linkage sugar. Unique molecular assembly motif of GlcNAc: The different aglycon conformations of methanesulfonamido and chloromethanesulfonamido derivatives of GlcNAc as compared to other sulfonamido analogues is a unique feature of their molecular assembly. This could be due to the cumulative effect of the direct hydrogen bonding between N1 and O1′ and C-H×××O interactions of the aglycon chain. Copyright