SOLID-PHASE SYNTHESIS AND CHARACTERIZATION OF O-DIMANNOSYLATED HEPTADECAPEPTIDE ANALOGS OF HUMAN INSULIN-LIKE GROWTH FACTOR-1 (IGF-1)

被引:32
作者
JANSSON, AM
MELDAL, M
BOCK, K
机构
[1] Department of Chemistry, Carlsberg Laboratory, DK-2500 Valby, Copenhagen
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1992年 / 13期
关键词
D O I
10.1039/p19920001699
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
N(alpha)-Fmoc-3-0-[Ac4-alpha-D-Manp-(1-->2)-Ac3-alpha-D-Manp-l-]-Thr-OPfp, 7, and N(alpha)-Fmoc-3-0-[AC4-alpha-D-Manp-(1-->2)-Ac3-alpha-D-Manp-1 -]-Ser-OPfp, 8, were prepared and used as building blocks in auto-mated continuous-flow solid-phase glycopeptide synthesis of two 0-glycosylated heptadecapeptide analogues of human insulin-like growth factor 1. The corresponding non-glycosylated fragments were also prepared, and comparative NMR studies regarding the influence of the sugar moiety on the peptide backbone showed only limited effects due to glycosylation.
引用
收藏
页码:1699 / 1707
页数:9
相关论文
共 33 条
[21]   SOLID-PHASE SYNTHESIS OF MONO-SACCHARIDE-CONTAINING AND DI-SACCHARIDE-CONTAINING GLYCOPEPTIDES [J].
LUNING, B ;
NORBERG, T ;
TEJBRANT, J .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1989, (17) :1267-1268
[22]   PENTAFLUOROPHENYL ESTERS FOR TEMPORARY CARBOXYL GROUP PROTECTION IN SOLID-PHASE SYNTHESIS OF N-LINKED GLYCOPEPTIDES [J].
MELDAL, M ;
BOCK, K .
TETRAHEDRON LETTERS, 1990, 31 (48) :6987-6990
[23]   PENTAFLUOROPHENYL ESTERS FOR THE TEMPORARY PROTECTION OF THE ALPHA-CARBOXY GROUP IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS [J].
MELDAL, M ;
JENSEN, KJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (06) :483-485
[24]  
Montreuil J, 1980, Adv Carbohydr Chem Biochem, V37, P157
[25]   CALIBRATION OF THE ANGULAR-DEPENDENCE OF THE AMIDE PROTON-C-ALPHA PROTON COUPLING-CONSTANTS, 3JHN-ALPHA, IN A GLOBULAR PROTEIN - USE OF 3JHN-ALPHA FOR IDENTIFICATION OF HELICAL SECONDARY STRUCTURE [J].
PARDI, A ;
BILLETER, M ;
WUTHRICH, K .
JOURNAL OF MOLECULAR BIOLOGY, 1984, 180 (03) :741-751
[26]   SOLID-PHASE SYNTHESIS OF O-GLYCOPEPTIDE SEQUENCES [J].
PAULSEN, H ;
MERZ, G ;
WEICHERT, U .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1988, 27 (10) :1365-1367
[27]  
PAULSEN H, 1990, LIEBIGS ANN CHEM, P1165
[28]   SYNTHESIS OF THE GLYCOPEPTIDE O-BETA-D-GALACTOPYRANOSYL-(1-]3)-O-(2-ACETAMIDO-2-DESOXY-ALPHA-D-GALACTOPYRANOSYL)-(1-]3)-L-SERINE AND L-THREONINE [J].
PAULSEN, H ;
HOLCK, JP .
CARBOHYDRATE RESEARCH, 1982, 109 (NOV) :89-107
[29]   MULTIPLE COLUMN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS [J].
PETERS, S ;
BIELFELDT, T ;
MELDAL, M ;
BOCK, K ;
PAULSEN, H .
TETRAHEDRON LETTERS, 1991, 32 (38) :5067-5070
[30]   NG-2,2,5,7,8-PENTAMETHYLCHROMAN-6-SULFONYL-L-ARGININE - A NEW ACID LABILE DERIVATIVE FOR PEPTIDE-SYNTHESIS [J].
RAMAGE, R ;
GREEN, J .
TETRAHEDRON LETTERS, 1987, 28 (20) :2287-2290