BUILDING-BLOCKS FOR GLYCOPEPTIDE SYNTHESIS - GLYCOSYLATION OF 3-MERCAPTOPROPIONIC ACID AND FMOC AMINO-ACIDS WITH UNPROTECTED CARBOXYL GROUPS

被引：89

作者：

ELOFSSON, M ^{[1
]}

WALSE, B ^{[1
]}

KIHLBERG, J ^{[1
]}

机构：

[1] LUND INST TECHNOL,CTR CHEM,POB 124,S-22100 LUND,SWEDEN

来源：

TETRAHEDRON LETTERS | 1991年 / 32卷 / 51期

关键词：

GLYCOSYLATED AMINO ACID; LEWIS ACID; MINIMAL PROTECTION; PERACETYLATED GLYCOSYL DONOR; GLYCOPEPTIDE;

D O I：

10.1016/0040-4039(91)80548-K

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

3-Mercaptopropionic acid and Fmoc amino acids, having unprotected carboxyl groups, were glycosylated with sugar 1,2-trans-acetates in 90 and 53-65% yields, respectively, under Lewis acid promotion. The synthesis of a neoglycopeptide illustrates the use of the building blocks in solid phase peptide synthesis.

引用

页码：7613 / 7616

页数：4

共 18 条

[1] IDENTIFICATION OF THE T-CELL AND IA CONTACT RESIDUES OF A T-CELL ANTIGENIC EPITOPE
ALLEN, PM
MATSUEDA, GR
EVANS, RJ
DUNBAR, JB
MARSHALL, GR
UNANUE, ER
[J]. NATURE, 1987, 327 (6124) : 713 - 715
[2] 9-FLUORENYLMETHOXYCARBONYL AMINO-PROTECTING GROUP
CARPINO, LA
HAN, GY
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1972, 37 (22) : 3404 - &
[3] CHACONFUERTES ME, 1975, CARBOHYD RES, V43, P51
[4] CHANG CD, 1980, INT J PEPT PROT RES, V15, P59
[5] IMPROVED METHOD FOR THE SYNTHESIS OF O-GLYCOSYLATED FLUOREN-9-YLMETHOXYCARBONYL AMINO-ACIDS TO BE USED IN SOLID-PHASE GLYCOPEPTIDE SYNTHESIS
DELATORRE, BG
TORRES, JL
BARDAJI, E
CLAPES, P
XAUS, N
JORBA, X
CALVET, S
ALBERICIO, F
VALENCIA, G
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1990, (14) : 965 - 967
[6] FILIRA F, 1990, INT J PEPT PROT RES, V36, P86
[7] JANSSON AM, 1990, TETRAHEDRON LETT, V31, P6991
[8] 2-(TRIMETHYLSILYL)ETHYL GLYCOSIDES .3. SYNTHESIS, ANOMERIC DEBLOCKING, AND TRANSFORMATION INTO 1,2-TRANS 1-O-ACYL SUGARS
JANSSON, K
AHLFORS, S
FREJD, T
KIHLBERG, J
MAGNUSSON, G
DAHMEN, J
NOORI, G
STENVALL, K
[J]. JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (24) : 5629 - 5647
[9] COLOR TEST FOR DETECTION OF FREE TERMINAL AMINO GROUPS IN SOLID-PHASE SYNTHESIS OF PEPTIDES
KAISER, E
COLESCOT.RL
BOSSINGE.CD
COOK, PI
[J]. ANALYTICAL BIOCHEMISTRY, 1970, 34 (02) : 595 - &
[10] SYNTHESIS OF GLYCOPEPTIDES, PARTIAL STRUCTURES OF BIOLOGICAL RECOGNITION COMPONENTS
KUNZ, H
[J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1987, 26 (04): : 294 - 308

← 1 2 →