A CONVENIENT DEGRADATION OF POLYOXIN D TO URACIL POLYOXIN-C - ACCESS TO KEY INTERMEDIATES AND SYNTHESIS OF ANTIFUNGAL ALPHA-AMINOACYL DERIVATIVES OF UPOC

被引：19

作者：

COOPER, AB

DESAI, J

LOVEY, RG

SAKSENA, AK

GIRIJAVALLABHAN, VM

GANGULY, AK

LOEBENBERG, D

PARMEGIANI, R

CACCIAPUOTI, A

机构：

[1] Schering-Plough Research Institute, Kenilworth, NJ 07033

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 1993年 / 3卷 / 06期

关键词：

D O I：

10.1016/S0960-894X(00)80291-7

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A convenient degradation of readily available polyoxin D under Edman conditions gave carboxyuracil polyoxin C 3 in high yield. Decarboxylation to uracil polyoxin C 5 (UPOC) and ring contraction to imidazolone compound 8, gave important nikkomycin Z and X intermediates respectively. Syntheses of new polyoxin/nikkomycin analogs 12-27, some with excellent chitin synthetase inhibition and Candida albicans whole cell activity are described. The importance of beta-methyl substituted amino acid side chains for whole cell activity is highlighted.

引用

页码：1079 / 1084

页数：6

共 34 条

[11] STUDIES ON MODE OF ACTION OF POLYOXINS .4. FURTHER STUDY ON RELATION OF POLYOXIN STRUCTURE TO CHITIN SYNTHETASE INHIBITION
HORI, M
KAKIKI, K
MISATO, T
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1974, 38 (04): : 691 - 698
[12] STUDIES ON MODE OF ACTION OF POLYOXINS .5. INTERACTION BETWEEN POLYOXIN AND ACTIVE-CENTER OF CHITIN SYNTHETASE
HORI, M
KAKIKI, K
MISATO, T
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1974, 38 (04): : 699 - 705
[13] STUDIES ON MODE OF ACTION OF POLYOXINS .3. RELATION OF POLYOXIN STRUCTURE TO CHITIN SYNTHETASE INHIBITION
HORI, ML
KAKIKI, K
SUZUKI, S
MISATO, T
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1971, 35 (08): : 1280 - &
[14] FORMATION OF 3-PHENYL-2-THIOHYDANTOINS FROM PHENYLTHIOCARBAMYL AMINO ACIDS
ILSE, D
EDMAN, P
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1963, 16 (03) : 411 - &
[15] POLYOXIN ANALOGS .2. SEMISYNTHETIC POLYOXINS - AMINOACYL DERIVATIVES OF POLYOXIN-C AND THEIR IN-VITRO ACTIVITY
ISONO, K
SUZUKI, S
AZUMA, T
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1971, 35 (12): : 1986 - &
[16] POLYOXINS - PYRIMIDINE NUCLEOSIDE PEPTIDE ANTIBIOTICS INHIBITING FUNGAL CELL-WALL BIOSYNTHESIS
ISONO, K
SUZUKI, S
[J]. HETEROCYCLES, 1979, 13 : 333 - 351
[17] STUDIES ON POLYOXINS, ANTIFUNGAL ANTIBIOTICS .13. STRUCTURE OF POLYOXINS
ISONO, K
ASAHI, K
SUZUKI, S
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (26) : 7490 - +
[18] STUDIES ON POLYOXINS ANTIFUNGAL ANTIBIOTICS .I. ISOLATION AND CHARACTERIZATION OF POLYOXINS A AND B
ISONO, K
NAGATSU, J
KAWASHIMA, Y
SUZUKI, S
[J]. AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1965, 29 (09): : 848 - +
[19] NUCLEOSIDE ANTIBIOTICS - STRUCTURE, BIOLOGICAL-ACTIVITY, AND BIOSYNTHESIS
ISONO, K
[J]. JOURNAL OF ANTIBIOTICS, 1988, 41 (12) : 1711 - 1739
[20] ISONO K, 1976, AGR BIOL CHEM TOKYO, V31, P190

← 1 2 3 4 →