MULTIPLE-COLUMN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS

被引:65
作者
PETERS, S [1 ]
BIELFELDT, T [1 ]
MELDAL, M [1 ]
BOCK, K [1 ]
PAULSEN, H [1 ]
机构
[1] CARLSBERG LAB,DEPT CHEM,DK-2500 COPENHAGEN,DENMARK
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 09期
关键词
D O I
10.1039/p19920001163
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The preparation of the two new building blocks N(alpha)-Fmoc-Ser(Ac3-alpha-D-GalpNAc)-OPfp 6 and N(alpha)-Fmoc-Thr(Ac3-alpha-D-GalpNAc)-OPfp 7 and their application in a simultaneous multiple-column solid-phase synthesis of 40 different O-glycopeptides from human intestinal mucin and porcine submaxillary gland mucin are described. All glycopeptides were obtained in excellent purity and were characterised by 1D- and 2D-H-1 NMR spectroscopy and amino acid analyses.
引用
收藏
页码:1163 / 1171
页数:9
相关论文
共 45 条
[1]   PREPARATION AND APPLICATION OF THE 5-(4-(9-FLUORENYLMETHYLOXYCARBONYL)AMINOMETHYL-3,5-DIMETHOXYPHENOXY)VALERIC ACID (PAL) HANDLE FOR THE SOLID-PHASE SYNTHESIS OF C-TERMINAL PEPTIDE AMIDES UNDER MILD CONDITIONS [J].
ALBERICIO, F ;
KNEIBCORDONIER, N ;
BIANCALANA, S ;
GERA, L ;
MASADA, RI ;
HUDSON, D ;
BARANY, G .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) :3730-3743
[2]   PEPTIDE-SYNTHESIS .10. USE OF PENTAFLUOROPHENYL ESTERS OF FLUORENYL METHOXYCARBONYLAMINO ACIDS IN SOLID-PHASE PEPTIDE-SYNTHESIS [J].
ATHERTON, E ;
CAMERON, LR ;
SHEPPARD, RC .
TETRAHEDRON, 1988, 44 (03) :843-857
[3]   PEPTIDE-SYNTHESIS .12. 3,4-DIHYDRO-4-OXO-1,2,3-BENZOTRIAZIN-3-YL ESTERS OF FLUORENYLMETHOXYCARBONYL AMINO-ACIDS AS SELF-INDICATING REAGENTS FOR SOLID-PHASE PEPTIDE-SYNTHESIS [J].
ATHERTON, E ;
HOLDER, JL ;
MELDAL, M ;
SHEPPARD, RC ;
VALERIO, RM .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1988, (10) :2887-2894
[4]  
ATHERTON E, 1980, J CHEM SOC P1, P538
[5]   SOLID-PHASE SYNTHESIS OF GLYCOPEPTIDE AMIDES UNDER MILD CONDITIONS - MORPHICEPTIN ANALOGS [J].
BARDAJI, E ;
TORRES, JL ;
CLAPES, P ;
ALBERICIO, F ;
BARANY, G ;
VALENCIA, G .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (03) :291-292
[6]   SYNTHESIS AND BIOLOGICAL-ACTIVITY OF O-GLYCOSYLATED MORPHICEPTIN ANALOGS [J].
BARDAJI, E ;
TORRES, JL ;
CLAPES, P ;
ALBERICIO, F ;
BARANY, G ;
RODRIGUEZ, RE ;
SACRISTAN, MP ;
VALENCIA, G .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1991, (07) :1755-1759
[7]  
Bardaji E, 1990, ANGEW CHEM, V102, P311
[8]   TOWARDS THE CHEMICAL SYNTHESIS OF PROTEINS [J].
BAYER, E .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1991, 30 (02) :113-129
[9]  
Bayer E, 1991, ANGEW CHEM, V103, P117
[10]   A COMPARISON OF ACID LABILE LINKAGE AGENTS FOR THE SYNTHESIS OF PEPTIDE C-TERMINAL AMIDES [J].
BERNATOWICZ, MS ;
DANIELS, SB ;
KOSTER, H .
TETRAHEDRON LETTERS, 1989, 30 (35) :4645-4648