A straightforward α-selective aromatic glycosylation and its application for stereospecific synthesis of 4-methylumbelliferyl α-T-antigen

被引：14

作者：

Chang, Shih-Sheng ^{[1
]}

Lin, Chun-Cheng ^{[2
]}

Li, Yaw-Kuen ^{[1
]}

Mong, Kwok-Kong Tony ^{[1
]}

机构：

[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu, Taiwan

[2] Natl Tsing Hua Univ, Dept Chem, Hsinchu, Taiwan

来源：

CARBOHYDRATE RESEARCH | 2009年 / 344卷 / 04期

关键词：

Stereoselective; Aromatic; Glycosylation; Imidate; alpha-T-Antigen; BETA-D-GLUCOPYRANOSIDES; N-ACETYLGALACTOSAMINIDASE; STEREOSELECTIVE-SYNTHESIS; OXOCARBENIUM ION; GLYCOSIDES; PHASE; DERIVATIVES; PHENOLS; OLIGOSACCHARIDES; XYLOSIDE;

D O I：

10.1016/j.carres.2008.12.013

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A practical and efficient alpha-selective aromatic glycosylation with simple per-O-acetyl glycopyranosyl trichloroacetimidates is reported. The method is particularly effective for L-fucosyl and 2-azido-2-deoxy-D-galatosaminyl imidates, with which exclusive alpha-selectivity was achieved. The synthetic utility of this method was demonstrated in the stereoselective synthesis of 4-methylumbelliferyl alpha-T-antigen. (C) 2008 Elsevier Ltd. All rights reserved.

引用

页码：432 / 438

页数：7

共 62 条

[1] Stereoselective single-step synthesis and X-ray crystallographic investigation of acetylated aryl 1,2-trans glycopyranosides and aryl 1,2-cis C2-hydroxy-glycopyranosides [J].

Aich, U ;

Loganathan, D .

CARBOHYDRATE RESEARCH, 2006, 341 (01) :19-28

[2] Metal catalyzed diazo transfer for the synthesis of azides from amines [J].

Alper, PB ;

Hung, SC ;

Wong, CH .

TETRAHEDRON LETTERS, 1996, 37 (34) :6029-6032

[3] Characterization of endo-α-N-acetylgalactosaminidase from Bacillus sp and syntheses of neo-oligosaccharides using its transglycosylation activity [J].

Ashida, H ;

Yamamoto, K ;

Murata, T ;

Usui, T ;

Kumagai, H .

ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 2000, 373 (02) :394-400

[4] CHEMICALLY SYNTHESIZED OLIGOSACCHARIDES, 1994 - A SEARCHABLE TABLE OF GLYCOSIDIC LINKAGES [J].

BARRESI, F ;

HINDSGAUL, O .

JOURNAL OF CARBOHYDRATE CHEMISTRY, 1995, 14 (08) :1043-1087

[5] A NOVEL MECHANISM OF GLYCOSIDE ANOMERIZATION [J].

BERVEN, LA ;

DOLPHIN, DH ;

WITHERS, SG .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1988, 110 (14) :4864-4866

[6] STEREOSELECTIVE SYNTHESIS OF 1-THIOGLYCOSIDES [J].

BLANCMUESSER, M ;

DEFAYE, J ;

DRIGUEZ, H .

CARBOHYDRATE RESEARCH, 1978, 67 (02) :305-328

[7] THE ACID-CATALYZED ANOMERIZATION OF THE D-GLUCOSE PENTAACETATES - A KINETIC THERMODYNAMIC AND MECHANISTIC STUDY [J].

BONNER, WA .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1951, 73 (06) :2659-2666

[8]

Bruckner R., 2002, ADV ORGANIC CHEM REA, P1

[9] STUDIES ON CELLULOLYTIC ENZYMES .1. USE OF 3,4-DINITROPHENYL GLYCOSIDES AS SUBSTRATES [J].

CAPON, B ;

THOMSON, JW .

BIOORGANIC CHEMISTRY, 1979, 8 (02) :147-173

[10] Building up key segments of N-glycans in the gas phase:: Intrinsic structural preferences of the α(1,3) and α(1,6) dimannosides [J].

Çarçabal, P ;

Hünig, I ;

Gamblin, DP ;

Liu, B ;

Jockusch, RA ;

Kroemer, RT ;

Snoek, LC ;

Fairbanks, AJ ;

Davis, BG ;

Simons, JP .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (06) :1976-1981

← 1 2 3 4 5 6 7 →