Bioactive carbohydrate derivatives

Shen, T. Y.; Li, J.P.; Dorn, Conrad P.; Ebel, David L.; Bugianesi, Rossana; Fecher, Ronald

doi:10.1016/s0008-6215(00)81580-3

Cited by 14 publications

(3 citation statements)

References 27 publications

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“…[19] Synthesis and characterization Synthesis of N-(b-d-glycosyl)methanesulfonamides: Per-Oacetylated b-d-glycosylamines were prepared by the reduction of per-O-acetylated b-d-glycosyl azides (1-8) using Pd/ C and hydrogen in dry CH 2 Cl 2 . Reaction of these glycosyl amines with methanesulfonyl chloride in the presence of triethylamine afforded the per-O-acetylated N-(b-d-glycosyl)methanesulfonamides (9)(10)(11)(12)(13)(14)(15)(16) in moderate to good yield with complete b-stereoselectivity (Scheme 1, Table 1). All the fully acetylated glycosyl methanesulfonamides (9)(10)(11)(12)(13)(14)(15)(16) were taken up for de-O-acetylation using BaA C H T U N G T R E N N U N G (OMe) 2 /MeOH at 0 8C.…”

Section: Resultsmentioning

confidence: 99%

“…Synthesis of N-(b-d-glycopyranosyl)chloromethanesulfonamides: 2,3,4,6-Tetra-O-acetylb-d-glucopyranosylamine was allowed to react with chloromethanesulfonyl chloride under the same reaction conditions as used for the synthesis of fully acetylated glycosyl methanesulfonamides (9)(10)(11)(12)(13)(14)(15)(16), which resulted in only 30 % yield of the expected product. To improve the yield, the reaction was performed with different bases (N,N-diiosopropylethylamine (DIEA), 4-dimethyl-A C H T U N G T R E N N U N G aminopyridine (DMAP), and pyridine) and pyridine was found to be the best among all the bases chosen for the reaction.…”

Section: Resultsmentioning

confidence: 99%

“…Glycosyl sulfonamides can be synthesized from the glycosyl amines14, 15 or from per‐ O ‐acetylated sugars 16. In the present work, acetylated glycosyl azides17 were chosen as starting material.…”

Section: Resultsmentioning

confidence: 99%

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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

Srivastava

Varghese

Loganathan

2013

Chemistry A European J

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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.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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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

Srivastava

Varghese

Loganathan

2013

Chemistry A European J

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Cooperativity of carbohydrate moiety orientation and β‐ turn stability is determined by intramolecular hydrogen bonds in protected glycopeptide models

1990

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The 2,3,4,6-Tetra-O-acetyl-beta-D-gluco-, and beta-D-galactopyranosides, as well as approximately 4:1 anomeric mixtures of alpha- and beta-mannopyranosides of Boc-X-Y-NHCH3 dipeptides (X-Y = Pro-Ser, Pro-D-Ser, Val-Ser, Val-D-Ser, and Gly-Ser) have been synthesized. CD and ir spectroscopic studies were performed to characterize the conformation of the glycosylated peptide backbone and examine the possible formation of intrapeptide and glycopeptide intramolecular H-bonds. It was found that O-glycosylated peptides containing a D-serine residue are likely to adopt a type II beta-turn while those with the Pro-Ser or Val-Ser sequence feature a type I (III) beta-turn in solution. Glycosylation also increases the magnitude of the CD bands, characteristic of the given type of beta-turns, which can be interpreted as an indication of the stabilization of the folded backbone conformation. Infrared data showed that in nonpolar solutions the peracetyl glycopeptides adopt both single- and double H-bonded conformations whose ratio, in some cases, depends on the position at C-2' of the H-bond acceptor acetoxy group. These data suggest that five-, seven-, or ten-membered glyco-turns may play an important role in fixing the steric orientation of the carbohydrate antennae systems in glycoproteins.

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Carbohydrates

Stevens

1996

Circular Dichroism and the Conformational Analysis of Biomolecules

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Bioactive carbohydrate derivatives

Cited by 14 publications

References 27 publications

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

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

Cooperativity of carbohydrate moiety orientation and β‐ turn stability is determined by intramolecular hydrogen bonds in protected glycopeptide models

Carbohydrates

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