EFFICIENT SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-SER/THR BUILDING-BLOCKS FOR SPPS OF O-GLCNAC GLYCOPEPTIDES

被引：24

作者：

MEINJOHANNS, E ^{[1
]}

MELDAL, M ^{[1
]}

BOCK, K ^{[1
]}

机构：

[1] CARLSBERG LAB,DEPT CHEM,DK-2500 VALBY,DENMARK

来源：

TETRAHEDRON LETTERS | 1995年 / 36卷 / 50期

关键词：

D O I：

10.1016/0040-4039(95)01941-A

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Suitably protected building blocks for solid-phase synthesis of beta-O-GlcNAc glycopeptides. N-alpha-Fmor-Ser(Ac-3-beta-D-GlcNAc)-OPfp 10 and N-alpha-Fmoc-Thr(AL(3)-beta-D-GlcNAc)-OPfp 11 have been synthesized by stereoselective glycosylation of N-alpha-Fmoc-Ser-OPfE 6 and N-alpha-Fmoc-Thr-OPfp 7, respectively. with the 2-trichloroethoxycarbonylamino (Teoc) glycosyl donors 3 and 5, followed by in situ reduction of the Teoc-group and simultaneous N-acetylation using zinc dust in tetrahydrofuranlacetic anhydridelacetic acid (3:2:1).

引用

页码：9205 / 9208

页数：4

共 50 条

[1] Efficient synthesis of O-(2-acetamido-2-deoxy- QQ -D-glucopyranosyl)- Ser/Thr building blocks for SPPS of O-GlcNAc glycopeptides
Meinjohanns, E.
Meldal, M.
Bock, K.
Tetrahedron Letters, 36 (50):
[2] Efficient synthesis of O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-serine and -threonine building blocks for glycopeptide formation
Saha, UK
Schmidt, RR
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12): : 1855 - 1860
[3] INTERACTION OF LYSOZYME WITH ISOMERIC PARA NITROPHENYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSIDES
KHORLIN, AY
SHASHKOVA, EA
ZURABYAN, SE
CARBOHYDRATE RESEARCH, 1972, 21 (02) : 269 - +
[4] CONVENIENT SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-SERINE AND THREONINE BUILDING-BLOCKS FOR SOLID-PHASE GLYCOPEPTIDE ASSEMBLY
VARGASBERENGUEL, A
MELDAL, M
PAULSEN, H
BOCK, K
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1994, (18): : 2615 - 2619
[5] SYNTHESIS OF 2-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-GLYCEROL AND 2-ACETAMIDO-3-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)2-DEOXY-D-GLUCOPYRANOSE BY OXAZOLINE METHOD
ANTONENKO, TS
ZURABYAN, SE
KHORLIN, AY
IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1970, (05): : 1153 - +
[6] SYNTHESIS OF O-[2-ACETAMIDO-3-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-2-DEOXY-BETA-D-GLUCOPYRANOSYL]-N-BENZYLOXYCARBONYL-L-SERINE METHYLAMIDE
KOCHETKO.NK
DEREVITS.VA
NOVIKOVA, OS
IZVESTIYA AKADEMII NAUK SSSR-SERIYA KHIMICHESKAYA, 1974, (01): : 179 - 181
[7] LYSOZYME SUBSTRATES . CHEMICAL SYNTHESIS OF P-NITROPHENYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]4)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]4)-2-ACETAMIDO-2-DEOXY-BETA-D-GLUCO-PYRANOSIDE AND ITS REACTION WITH LYSOZYME
OSAWA, T
NAKAZAWA, Y
BIOCHIMICA ET BIOPHYSICA ACTA, 1966, 130 (01) : 56 - &
[8] SYNTHESIS OF 2-ACETAMIDO-6-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-2-DEOXY-D-GLUCOPYRANOSE
BUNDLE, D
SHAW, N
CARBOHYDRATE RESEARCH, 1972, 21 (02) : 211 - &
[9] SYNTHETIC MUCIN FRAGMENTS - METHYL 6-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-BETA-D-GALACTOPYRANOSIDE, METHYL 3,4-DI-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-BETA-D-GALACTOPYRANOSIDE, AND METHYL O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-O-BETA-D-GALACTOPYRANOSYL-(1-]3)-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-(1-]3)-BETA-D-GALACTOPYRANOSIDE
ABBAS, SA
KOHATA, K
MATTA, KL
CARBOHYDRATE RESEARCH, 1987, 161 (01) : 39 - 47
[10] SYNTHETIC STUDIES IN CARBOHYDRATES .36. SYNTHETIC MUCIN FRAGMENTS - BENZYL 2-ACETAMIDO-6-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-2-DEOXY-3-O-BETA-D-GALACTOPYRANOSYL-ALPHA-D-GALACTOPYRANOSIDE AND BENZYL 2-ACETAMIDO-6-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-3-O-[6-O-(2-ACETAMIDO-2-DEOXY-BETA-D-GLUCOPYRANOSYL)-BETA-D-GALACTOPYRANOSYL]-2-DEOXY-ALPHA-D-GALACTOPYRANOSID
PISKORZ, CF
ABBAS, SA
MATTA, KL
CARBOHYDRATE RESEARCH, 1984, 126 (01) : 115 - 124

← 1 2 3 4 5 →