SOLID-PHASE N-GLYCOPEPTIDE SYNTHESIS USING ALLYL SIDE-CHAIN PROTECTED FMOC-AMINO ACIDS

被引:31
作者
KATES, SA
DELATORRE, BG
ERITJA, R
ALBERICIO, F
机构
[1] MILLIPORE CORP,BEDFORD,MA 01730
[2] CSIC,CID,E-08034 BARCELONA,SPAIN
关键词
GLYCOPEPTIDES; ALLYL ESTERS; ORTHOGONAL PROTECTION; SOLID-PHASE SYNTHESIS;
D O I
10.1016/S0040-4039(00)79958-8
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A method for the preparation of glycopeptides using a three-dimensional orthogonal solid-phase strategy (Fmoc/tBu/allyl) with selective allyl removal and direct coupling of glycosylamines to the carboxyl function while the peptide is attached to the resin is described.
引用
收藏
页码:1033 / 1034
页数:2
相关论文
共 16 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
    ALBERICIO, F
    KNEIBCORDONIER, N
    BIANCALANA, S
    GERA, L
    MASADA, RI
    HUDSON, D
    BARANY, G
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (12) : 3730 - 3743
  • [2] A CONVERGENT APPROACH TO THE CHEMICAL SYNTHESIS OF ASPARAGINE-LINKED GLYCOPEPTIDES
    ANISFELD, ST
    LANSBURY, PT
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (21) : 5560 - 5562
  • [3] BARANY G, 1993, 22ND P EUR PEPT S, P267
  • [4] SOLID-PHASE SYNTHESIS OF GLYCOPEPTIDE AMIDES UNDER MILD CONDITIONS - MORPHICEPTIN ANALOGS
    BARDAJI, E
    TORRES, JL
    CLAPES, P
    ALBERICIO, F
    BARANY, G
    VALENCIA, G
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1990, 29 (03): : 291 - 292
  • [5] BECKER G, 1988, PEPTIDES 1988, P157
  • [6] HANDA BK, 1992, INT J PEPT PROT RES, V40, P66
  • [7] SOLID-PHASE SYNTHESIS OF GLYCOPEPTIDES - GLYCOSYLATION OF RESIN-BOUND SERINE-PEPTIDES BY 3,4,6-TRI-O-ACETYL-D-GLUCOSE-OXAZOLINE
    HOLLOSI, M
    KOLLAT, E
    LACZKO, I
    MEDZIHRADSZKY, KF
    THURIN, J
    OTVOS, L
    [J]. TETRAHEDRON LETTERS, 1991, 32 (12) : 1531 - 1534
  • [8] AUTOMATED ALLYL CLEAVAGE FOR CONTINUOUS-FLOW SYNTHESIS OF CYCLIC AND BRANCHED PEPTIDES
    KATES, SA
    DANIELS, SB
    ALBERICIO, F
    [J]. ANALYTICAL BIOCHEMISTRY, 1993, 212 (02) : 303 - 310
  • [9] A NOVEL, CONVENIENT, 3-DIMENSIONAL ORTHOGONAL STRATEGY FOR SOLID-PHASE SYNTHESIS OF CYCLIC-PEPTIDES
    KATES, SA
    SOLE, NA
    JOHNSON, CR
    HUDSON, D
    BARANY, G
    ALBERICIO, F
    [J]. TETRAHEDRON LETTERS, 1993, 34 (10) : 1549 - 1552
  • [10] GLYCOPEPTIDES OF BIOLOGICAL INTEREST - A CHALLENGE FOR CHEMICAL SYNTHESIS
    KUNZ, H
    [J]. PURE AND APPLIED CHEMISTRY, 1993, 65 (06) : 1223 - 1232