An N-acetylglucosamine containing glycopeptide - synthesis and structure assignment

被引:8
作者
Saha, UK
Griffith, LS
Rademann, J
Geyer, A
Schmidt, RR
机构
[1] UNIV KONSTANZ,FAK CHEM,D-78457 CONSTANCE,GERMANY
[2] UNIV BONN,INST TIERPHYSIOL & ANAT,D-53115 BONN,GERMANY
关键词
O-glycopeptides; O-linked N-acetylglucosamine; synthesis; conformational analysis;
D O I
10.1016/S0008-6215(97)00212-7
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 nonapeptide sequence alignment known to be O-glycosylated at serine and/or threonine residues by N-acetylglucosamine (2-acetamido-2-deoxy-D-glucose) was chemically synthesized with and without O-GlcNAc residues. A detailed conformational analysis was performed which displays the preferred conformation of the peptide backbone and the influence of the sugar residues. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:21 / 28
页数:8
相关论文
共 30 条
[21]   STRUCTURE AND DYNAMICS OF A SYNTHETIC O-GLYCOSYLATED CYCLOPEPTIDE IN SOLUTION DETERMINED BY NMR-SPECTROSCOPY AND MD CALCULATIONS [J].
KESSLER, H ;
MATTER, H ;
GEMMECKER, G ;
KOTTENHAHN, M ;
BATS, JW .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (12) :4805-4818
[22]   BUILDUP RATES OF THE NUCLEAR OVERHAUSER EFFECT MEASURED BY TWO-DIMENSIONAL PROTON MAGNETIC-RESONANCE SPECTROSCOPY - IMPLICATIONS FOR STUDIES OF PROTEIN CONFORMATION [J].
KUMAR, A ;
WAGNER, G ;
ERNST, RR ;
WUTHRICH, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (13) :3654-3658
[23]   STRUCTURALLY DEFINED SYNTHETIC CANCER VACCINES - ANALYSIS OF STRUCTURE, GLYCOSYLATION AND RECOGNITION OF CANCER-ASSOCIATED MUCIN, MUC-1 DERIVED PEPTIDES [J].
LIU, XH ;
SEJBAL, J ;
KOTOVYCH, G ;
KOGANTY, RR ;
REDDISH, MA ;
JACKSON, L ;
GANDHI, SS ;
MENDONCA, AJ ;
LONGENECKER, BM .
GLYCOCONJUGATE JOURNAL, 1995, 12 (05) :607-617
[24]   COMPARISON OF N-DTS AND N-ALOC IN THE SOLID-PHASE SYNTHESES OF O-GLCNAC GLYCOPEPTIDE FRAGMENTS OF RNA-POLYMERASE-II AND MAMMALIAN NEUROFILAMENTS [J].
MEINJOHANNS, E ;
VARGASBERENGUEL, A ;
MELDAL, M ;
PAULSEN, H ;
BOCK, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1995, (17) :2165-2175
[25]   Stabilization of proteins by glycosylation examined by NMR analysis of a fucosylated proteinase inhibitor [J].
Mer, G ;
Hietter, H ;
Lefevre, JF .
NATURE STRUCTURAL BIOLOGY, 1996, 3 (01) :45-53
[26]   NUCLEAR MAGNETIC RESONANCE STUDY OF SOME ALPHA-AMINO ACIDS .1. COUPLING CONSTANTS IN ALKALINE AND ACIDIC MEDIUM [J].
PACHLER, KGR .
SPECTROCHIMICA ACTA, 1963, 19 (12) :2085-2092
[27]   NUCLEAR MAGNETIC RESONANCE STUDY OF SOME ALPHA-AMINO ACIDS .2. ROTATIONAL ISOMERISM [J].
PACHLER, KGR .
SPECTROCHIMICA ACTA, 1964, 20 (04) :581-587
[28]   Efficient synthesis of O-(2-acetamido-2-deoxy-beta-D-glucopyranosyl)-serine and -threonine building blocks for glycopeptide formation [J].
Saha, UK ;
Schmidt, RR .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (12) :1855-1860
[29]  
SCHULTHEISSREIM.P, 1983, ANGEW CHEM, V95, P64
[30]   O-GLYCOPEPTIDE SYNTHESIS USING 9-FLUORENYLMETHOXYCARBONYL (FMOC)-PROTECTED SYNTHETIC UNITS [J].
SCHULTHEISSREIMANN, P ;
KUNZ, H .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1983, 22 (01) :62-63