A CONVENIENT PROCEDURE FOR THE PREPARATION OF FULLY-PROTECTED C-TERMINAL GLYCOPEPTIDES

被引:7
作者
BAUMAN, AC [1 ]
BRODERICK, JS [1 ]
DACUS, RM [1 ]
GROVER, DA [1 ]
TRZUPEK, LS [1 ]
机构
[1] FURMAN UNIV,DEPT CHEM,GREENVILLE,SC 29613
关键词
D O I
10.1016/S0040-4039(00)61586-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The acetic acid catalyzed reaction of the free amine form of a glycosylated serine ester with amino acids or peptides built-up on a Kaiser-DeGrado polystyrene benzophenone oxime resin affords C-terminal glycopeptides in a fully-protected form suitable for further chemical manipulation.
引用
收藏
页码:7019 / 7022
页数:4
相关论文
共 14 条
[1]   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
[2]  
BIEFELDT T, 1992, ANGEW CHEM, V104, P881
[3]   SOLID-PHASE SYNTHESIS OF PROTECTED PEPTIDES ON A POLYMER-BOUND OXIME - PREPARATION OF SEGMENTS COMPRISING THE SEQUENCE OF A CYTO-TOXIC 26-PEPTIDE ANALOG [J].
DEGRADO, WF ;
KAISER, ET .
JOURNAL OF ORGANIC CHEMISTRY, 1982, 47 (17) :3258-3261
[4]   POLYMER-BOUND OXIME ESTERS AS SUPPORTS FOR SOLID-PHASE PEPTIDE-SYNTHESIS - PREPARATION OF PROTECTED PEPTIDE-FRAGMENTS [J].
DEGRADO, WF ;
KAISER, ET .
JOURNAL OF ORGANIC CHEMISTRY, 1980, 45 (07) :1295-1300
[5]   IMPROVED METHOD FOR THE SYNTHESIS OF O-GLYCOSYLATED FLUOREN-9-YLMETHOXYCARBONYL AMINO-ACIDS TO BE USED IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS [J].
DELATORRE, BG ;
TORRES, JL ;
BARDAJI, E ;
CLAPES, P ;
XAUS, N ;
JORBA, X ;
CALVET, S ;
ALBERICIO, F ;
VALENCIA, G .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) :965-967
[6]   SOLID-PHASE SYNTHESIS AND CHARACTERIZATION OF O-DIMANNOSYLATED HEPTADECAPEPTIDE ANALOGS OF HUMAN INSULIN-LIKE GROWTH FACTOR-1 (IGF-1) [J].
JANSSON, AM ;
MELDAL, M ;
BOCK, K .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (13) :1699-1707
[7]   RATE CONSTANTS FOR PEPTIDE PARA-NITROPHENYL ESTER COUPLING REACTIONS IN DIMETHYLFORMAMIDE - MODEL FOR STERIC INTERACTIONS IN PEPTIDE-BOND FORMING TRANSITION-STATE [J].
KEMP, DS ;
CHOONG, SLH ;
PEKAAR, J .
JOURNAL OF ORGANIC CHEMISTRY, 1974, 39 (26) :3841-3847
[8]   SOLID-PHASE SYNTHESIS OF PEPTIDES AND GLYCOPEPTIDES ON POLYMERIC SUPPORTS WITH ALLYLIC ANCHOR GROUPS [J].
KUNZ, H ;
DOMBO, B .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (05) :711-713
[9]  
Kunz H., 1992, TRENDS GLYCOSCI GLYC, V4, P71
[10]  
LUENIG B, 1991, GLYCONJUGATE J, V8, P450