Showing papers on "Glucal published in 1998"
TL;DR: In this paper, a fluorous tribenzyl glucal derivative was combined with excess diacetone galactose to make a disaccharide, which was then used to synthesize oligosaccharides.
94 citations
TL;DR: An efficient solid-phase synthesis of three N-linked glycopeptides based on glycal assembly is presented, finding the peptide domain can be extended while the ensemble remains bound to the polymer.
Abstract: Solid-supported synthesis can be conducted to produce a variety of glycopeptides in good overall yields. The carbohydrates are formed by the glycal assembly method. The polymer-bound construct terminates in a glycal. The terminal double bond can be functionalized to provide a C2−N-acetyl glucosamine linkage with an amino group in the anomeric position. The latter can be coupled, in a convergent manner, to the γ-carboxyl group of an aspartyl residue on a preformed peptide. Iodosulfonamidation of the polymer-bound glucal to the N-acetyl glucosamine using anthracenesulfonamide was crucial for the success of the solid-phase synthesis. This general method was employed in the formation of a variety of glycopeptides.
65 citations
TL;DR: In this paper, a mechanistic cycle was proposed to explain the regio-and stereoselectivity of the reaction, and the mononuclear rhodium complex trans-[RhCl(CO)(P(O-o-tBuC6H4)3)] was isolated at the end of the catalytic reaction by breaking the dinuclear complexes used as catalyst precursors.
44 citations
TL;DR: In this paper, a series of 4-(4,6-di- O -benzyl-2,3-dideoxy- β - d - erythro -hex-2-enopyranosyl)-3-methylpyrazoles having the N-1 free or substituted by the foregoing groups, and the C-5 substituted by a methyl or phenyl group.
31 citations
19 citations
TL;DR: In this paper, the authors proposed a method to give the dimethyl acetal of 2-C-formyl-Dalditol derivatives using the catalytic system [Rh(µ-OMe)(cod)]2/P(O-o-ButC6H4)3/PPTS is strongly dependent on the protecting groups on the carbohydrate.
14 citations
TL;DR: The chemical modification study and pH profile study of this antibody indicated that carboxyl group(s) in the antigen binding site involved in catalytic mechanism.
3 citations
TL;DR: Themodynamic stability of 3-C-nitro-d -glucol and -d -allal derivatives as well as the corresponding 5a-carba sugars was reproduced by ab initio (6-31G ∗ ) calculations as mentioned in this paper.
2 citations
2 citations
TL;DR: In this paper, the authors investigated the regioselectivity of the glycosylation reaction using p -nitrophenyl β-d -galactopyranoside, β- d -mannopyranoyl fluoride and d -glucal donors and acceptors.
Abstract: The synthesis of several oligosaccharides, in yields up to 65%, has been achieved by utilizing the transglycosylation activity of Agrobacterium sp. β-glucosidase (EC 3.2.1.21). The regioselectivity of the glycosylation reaction was investigated using p -nitrophenyl β- d -galactopyranoside, β- d -mannopyranosyl fluoride and d -glucal as glycosyl donors and a series of phenyl 1-thio-, benzyl 1-thio-, and benzyl β- d -glycopyranosides as glycosyl acceptors. The isolated products were determined to contain a mixture of β -(1 → 3) and/or β -(1 → 4) glycosidic linkages for all glycosyl acceptors, except for β- d - galacto -configured acceptors where a mixture of β -(1 → 3) and β -(1 → 6) linkages was observed. The wide range of glycosyl donors and acceptors utilized by the enzyme in transglycosylation experiments demonstrates the versatility of this system for the aqueous-phase synthesis of oligosaccharides.
1 citations