Convenient synthesis of 7′ and 6′-bromo-D-tryptophan and their derivatives by enzymatic optical resolution using D-aminoacylase

被引:49
作者
Konda-Yamada, Y [1 ]
Okada, C [1 ]
Yoshida, K [1 ]
Umeda, Y [1 ]
Arima, S [1 ]
Sato, N [1 ]
Kai, T [1 ]
Takayanagi, H [1 ]
Harigaya, Y [1 ]
机构
[1] Kitasato Univ, Sch Pharmaceut Sci, Minato Ku, Tokyo 1088641, Japan
关键词
7 ' and 6 '-bromo-D-tryptophan; synthesis; D-aminoacylase; optical resolution;
D O I
10.1016/S0040-4020(02)00909-2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Compounds 7' and 61-bromo-D-tryptophan (1 and 2) which are important derivatives for the synthesis of the chloropeptin and kistamycin A, respectively, were conveniently synthesized by optical resolution from N-acetyl-7' and 6-bromo-DL-tryptophan ((RS)-5 and (RS)-14) using D-aminoacylase. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:7851 / 7861
页数:11
相关论文
共 23 条
[1]   SYNTHESIS OF 5-BROMOTRYPTOPHAN AND 7-BROMOTRYPTOPHAN AND OF [5-BROMOTRYPTOPHAN9]-BETA-CORTICOTROPHIN-(1-24)-TETRACOSAPEPTIDE, A HIGHLY POTENT CORTICOTROPIN ANALOG [J].
ALLEN, MC ;
BRUNDISH, DE ;
WADE, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1980, (09) :1928-1932
[2]   THE REACTION OF VINYL GRIGNARD-REAGENTS WITH 2-SUBSTITUTED NITROARENES - A NEW APPROACH TO THE SYNTHESIS OF 7-SUBSTITUTED INDOLES [J].
BARTOLI, G ;
PALMIERI, G ;
BOSCO, M ;
DALPOZZO, R .
TETRAHEDRON LETTERS, 1989, 30 (16) :2129-2132
[3]   Synthetic studies towards western and eastern macropolypeptide subunits of kistamycin [J].
Beugelmans, R ;
Roussi, G ;
Zamora, EG ;
Carbonnelle, AC .
TETRAHEDRON, 1999, 55 (16) :5089-5112
[4]  
BIRNBAUM SM, 1952, J BIOL CHEM, V194, P445
[5]   Total synthesis of HUN-7293 [J].
Boger, DL ;
Keim, H ;
Oberhauser, B ;
Schreiner, EP ;
Foster, CA .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1999, 121 (26) :6197-6205
[6]   FACILE SYNTHESIS OF TERT-BUTYL ESTER OF N-PROTECTED AMINO-ACIDS WITH TERT-BUTYL BROMIDE [J].
CHEVALLET, P ;
GARROUSTE, P ;
MALAWSKA, B ;
MARTINEZ, J .
TETRAHEDRON LETTERS, 1993, 34 (46) :7409-7412
[7]  
FUKAGAWA Y, J ANTIBIOT, V33, P543
[8]   Stereostructure of (-)-chloropeptin I, a novel inhibitor of gp120-CD4 binding, via high-temperature molecular dynamics, Monte Carlo conformational searching, and NMR spectroscopy [J].
Gouda, H ;
Matsuzaki, K ;
Tanaka, H ;
Hirono, S ;
Omura, S ;
McCauley, JA ;
Sprengeler, PA ;
Furst, GT ;
Smith, AB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1996, 118 (51) :13087-13088
[9]  
GREENSTEIN JP, 1984, CHEM AMINO ACIDS, V1, P715
[10]  
HANGARTNER Y, 1979, J ORG CHEM, V44, P3741