ON THE DNA RECOGNITION ROLE OF THE CARBOHYDRATE SECTOR IN CALICHEAMICIN - A COMPARISON OF DNA-CLEAVING CAPACITY OF ENANTIOMERIC CALICHEAMICINONES

被引:32
作者
AIYAR, J [1 ]
HITCHCOCK, SA [1 ]
DENHART, D [1 ]
LIU, KKC [1 ]
DANISHEFSKY, SJ [1 ]
CROTHERS, DM [1 ]
机构
[1] YALE UNIV,DEPT CHEM,NEW HAVEN,CT 06511
来源
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH | 1994年 / 33卷 / 08期
关键词
D O I
10.1002/anie.199408551
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Surprisingly, the “unnatural” aglycone analogue 1 (R  Ac) of calicheamicin cleaves double‐stranded DNA more effectively than the natural ent‐1. If the efficiency of this cleavage for the enediyne effector is determined essentially by its configuration, the sequence selectivity of calicheamicin is rooted in the saccharide recognition sector. (Figure Presented.) Copyright © 1994 by VCH Verlagsgesellschaft mbH, Germany
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页码:855 / 858
页数:4
相关论文
共 36 条
[1]  
AIYER J, 1992, J AM CHEM SOC, V114, P7552
[2]   ENANTIOMERIC SELECTIVITY IN BINDING TRIS(PHENANTHROLINE)ZINC(II) TO DNA [J].
BARTON, JK ;
DANNENBERG, JJ ;
RAPHAEL, AL .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (18) :4967-4969
[3]   BINDING MODES AND BASE SPECIFICITY OF TRIS(PHENANTHROLINE)RUTHENIUM(II) ENANTIOMERS WITH NUCLEIC-ACIDS - TUNING THE STEREOSELECTIVITY [J].
BARTON, JK ;
GOLDBERG, JM ;
KUMAR, CV ;
TURRO, NJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (08) :2081-2088
[4]   CHIRAL DISCRIMINATION IN THE COVALENT BINDING OF BIS(PHENANTHROLINE)DICHLORORUTHENIUM(II) TO B-DNA [J].
BARTON, JK ;
LOLIS, E .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1985, 107 (03) :708-709
[5]   TOTAL SYNTHESIS AND PRELIMINARY EVALUATION OF (+)-DUOCARMYCIN AND ENT-(-)-DUOCARMYCIN SA [J].
BOGER, DL ;
MACHIYA, K ;
HERTZOG, DL ;
KITOS, PA ;
HOLMES, D .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (20) :9025-9036
[6]  
BOGER DL, 1994, IN PRESS BIOORG MED
[7]  
BOGER DL, 1994, IN PRESS J AM CHEM S, V116
[8]   TOTAL SYNTHESIS OF CALICHEAMICINONE - A SOLUTION TO THE PROBLEM OF THE ELUSIVE URETHANE [J].
CABAL, MP ;
COLEMAN, RS ;
DANISHEFSKY, SJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1990, 112 (08) :3253-3255
[9]  
DEDON PC, 1990, J BIOL CHEM, V265, P14713
[10]   THE CARBOHYDRATE DOMAIN OF CALICHEAMICIN GAMMA-1(I) DETERMINES ITS SEQUENCE SPECIFICITY FOR DNA CLEAVAGE [J].
DRAK, J ;
IWASAWA, N ;
DANISHEFSKY, S ;
CROTHERS, DM .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1991, 88 (17) :7464-7468