NEW EFFICIENT STRATEGY FOR THE INCORPORATION OF (S)-ISOSERINE INTO PEPTIDES

被引：35

作者：

BURGER, K

WINDEISEN, E

PIRES, R

机构：

[1] Department of Organic Chemistry, University Leipzig, D-04103 Leipzig

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1995年 / 60卷 / 23期

关键词：

D O I：

10.1021/jo00128a042

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new efficient synthesis of (S)-isoserine derivatives from (S)-malic acid using hexafluoroacetone as protecting and activating reagent is described. Via this route (S)-isoserine is obtained as mono- and diactivated species suitable for the incorporation of isoserine into the N- and C-terminal positions of peptides.

引用

页码：7641 / 7645

页数：5

共 32 条

[1] BLAGBROUGH IS, 1986, TETRAHEDRON LETT, P1251
[2] BOURZAT JD, 1993, TETRAHEDRON LETT, P6049
[3] CARNITINE - METABOLISM AND FUNCTIONS
BREMER, J
[J]. PHYSIOLOGICAL REVIEWS, 1983, 63 (04) : 1420 - 1480
[4] BURGER K, 1991, LIEBIGS ANN CHEM, P1365
[5] BURGER K, UNPUB
[6] DONDONI A, 1993, SYNTHESIS-STUTTGART, P1162
[7] FLUORO KETONE CONTAINING PEPTIDES AS INHIBITORS OF HUMAN RENIN
FEARON, K
SPALTENSTEIN, A
HOPKINS, PB
GELB, MH
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1987, 30 (09) : 1617 - 1622
[8] Goldschmidt S., 1952, LIEBIGS ANN CHEM, V575, P217
[9] PREPARATION AND BIOLOGICAL-ACTIVITY OF NOVEL AMINO-ACID ANALOGS OF BUTIROSIN
HASKELL, TH
RODEBAUGH, R
PLESSAS, N
WATSON, D
WESTLAND, RD
[J]. CARBOHYDRATE RESEARCH, 1973, 28 (02) : 263 - 280
[10] TATUMINE, A PEPTIDE FROM BACILLUS-BREVIS VM4-572-403
HEANEYKIERAS, J
KURYLOBOROWSKA, Z
[J]. JOURNAL OF ANTIBIOTICS, 1980, 33 (04) : 359 - 363

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