SYNTHESIS, STEREOCHEMISTRY, AND BIOLOGICAL PROPERTIES OF THE DEPIGMENTING AGENTS, MELANOSTATIN, FELDAMYCIN AND ANALOGS

被引:17
作者
IMAE, K
KAMACHI, H
YAMASHITA, H
OKITA, T
OKUYAMA, S
TSUNO, T
YAMASAKI, T
SAWADA, Y
OHBAYASHI, M
NAITO, T
OKI, T
机构
[1] Bristol-Myers Squibb Research Institute, Meguro-ku, Tokyo 153
关键词
ACID; DERIVATIVES; FR900490; FUNGUS;
D O I
10.7164/antibiotics.44.76
中图分类号
Q81 [生物工程学(生物技术)]; Q93 [微生物学];
学科分类号
071005 ; 0836 ; 090102 ; 100705 ;
摘要
Syntheses of melanostatin and feldamycin have been completed from L-serine and L-theronine, respectively, and the configuration of unknown asymmetric carbons determined. Feldamycin analogs have also been prepared and the L-tryptophyl analog was the most potent in the depigmentation of Streptomyces bikiniensis and B16 melanoma cells.
引用
收藏
页码:76 / 85
页数:10
相关论文
共 12 条
[1]   STRUCTURE OF FELDAMYCIN [J].
ARGOUDELIS, AD ;
MIZSAK, SA ;
BACZYNSKYJ, L ;
WNUK, RJ .
JOURNAL OF ANTIBIOTICS, 1976, 29 (10) :1117-1119
[2]   ANTIBIOTICS PRODUCED BY STREPTOMYCES-FICELLUS .2. FELDAMYCIN AND NOJIRIMYCIN [J].
ARGOUDELIS, AD ;
REUSSER, F ;
MIZSAK, SA ;
BACZYNSKYJ, L .
JOURNAL OF ANTIBIOTICS, 1976, 29 (10) :1007-1014
[3]   MELANOSTATIN, A NEW MELANIN SYNTHESIS INHIBITOR - PRODUCTION, ISOLATION, CHEMICAL-PROPERTIES, STRUCTURE AND BIOLOGICAL-ACTIVITY [J].
ISHIHARA, Y ;
OKA, M ;
TSUNAKAWA, M ;
TOMITA, K ;
HATORI, M ;
YAMAMOTO, H ;
KAMEI, H ;
MIYAKI, T ;
KONISHI, M ;
OKI, T .
JOURNAL OF ANTIBIOTICS, 1991, 44 (01) :25-32
[4]   STUDIES ON HYDROXY AMINO-ACIDS .4. SYNTHESES OF SEVERAL PEPTIDES CONTAINING AZIRIDINECARBOXYLIC ACID DERIVED FROM CORRESPONDING HYDROXY AMINO-ACID DERIVATIVES [J].
NAKAGAWA, Y ;
NAKAJIMA, K ;
OKAWA, K ;
TSUNO, T ;
IWAI, M ;
KAWAI, H .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1972, 45 (04) :1162-+
[5]   STUDIES ON AZIRIDINE-2-CARBOXYLIC ACID .1. SYNTHESIS OF OPTICALLY-ACTIVE L-AZIRIDINE-2-CARBOXYLIC ACID AND ITS DERIVATIVES [J].
NAKAJIMA, K ;
TAKAI, F ;
TANAKA, T ;
OKAWA, K .
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1978, 51 (05) :1577-1578
[6]   SYNTHESIS OF ALPHA-N-METHYLATED HISTIDINES [J].
REINHOLD, VN ;
ISHIKAWA, Y ;
MELVILLE, DB .
JOURNAL OF MEDICINAL CHEMISTRY, 1968, 11 (02) :258-&
[7]  
SETOI H, 1989, CHEM PHARM BULL, V37, P1126
[8]   A NEW IMMUNOMODULATOR, FR-900490 [J].
SHIBATA, T ;
NAKAYAMA, O ;
OKUHARA, M ;
TSURUMI, Y ;
TERANO, H ;
KOHSAKA, M .
JOURNAL OF ANTIBIOTICS, 1988, 41 (09) :1163-1169
[9]   STRUCTURE AND SYNTHESIS OF FR900490, A NEW IMMUNOMODULATING PEPTIDE ISOLATED FROM A FUNGUS [J].
SHIGEMATSU, N ;
SETOI, H ;
UCHIDA, I ;
SHIBATA, T ;
TERANO, H ;
HASHIMOTO, M .
TETRAHEDRON LETTERS, 1988, 29 (40) :5147-5150
[10]  
SMRT J, 1960, Patent No. 2958691