SYNTHESIS OF NOVEL THIAZOLE-CONTAINING DNA MINOR GROOVE BINDING OLIGOPEPTIDES RELATED TO THE ANTIBIOTIC DISTAMYCIN

被引:56
作者
RAO, KE [1 ]
BATHINI, Y [1 ]
LOWN, JW [1 ]
机构
[1] UNIV ALBERTA,DEPT CHEM,EDMONTON T6G 2G2,ALBERTA,CANADA
关键词
D O I
10.1021/jo00289a057
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The synthesis of novel thiazole-bearing oligopeptides related to the antibiotic distamycin is described. These lexitropsins, or information reading agents, are designed to test the principle of DNA base site exclusion or avoidance as well as base pair acceptance in molecular recognition of oligopeptides for DNA. The first group of compounds, therefore, has the sulfur atom aligned inward to the DNA minor groove, whereas the second group of agents has the sulfur atom directed away from the DNA minor groove. All six compounds synthesized bind to double helical DNA, and their binding constants to calf thymus DNA and relative to distamycin and netropsin are reported. © 1990, American Chemical Society. All rights reserved.
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页码:728 / 737
页数:10
相关论文
共 45 条
[41]   ANTIVIRAL EFFECT OF AN OLIGO(NUCLEOSIDE METHYLPHOSPHONATE) COMPLEMENTARY TO THE SPLICE JUNCTION OF HERPES-SIMPLEX VIRUS TYPE-1 IMMEDIATE EARLY PRE-MESSENGER RNA-4 AND PRE-MESSENGER RNA-5 [J].
SMITH, CC ;
AURELIAN, L ;
REDDY, MP ;
MILLER, PS ;
TSO, POP .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (09) :2787-2791
[42]   CARBOXY DERIVATIVES OF SULFONAMIDOTHIAZOLES [J].
SPRAGUE, JM ;
LINCOLN, RM ;
ZIEGLER, C .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1946, 68 (02) :266-269
[43]   INHIBITION OF ROUS-SARCOMA VIRAL-RNA TRANSLATION BY A SPECIFIC OLIGODEOXYRIBONUCLEOTIDE [J].
STEPHENSON, ML ;
ZAMECNIK, PC .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1978, 75 (01) :285-288
[44]  
TAKEDA Y, 1983, SCIENCE, V221, P1020, DOI 10.1126/science.6308768
[45]   SPECIFIC-INHIBITION OF MESSENGER-RNA TRANSLATION BY COMPLEMENTARY OLIGONUCLEOTIDES COVALENTLY LINKED TO INTERCALATING AGENTS [J].
TOULEM, JJ ;
KRISCH, HM ;
LOREAU, N ;
THUONG, NT ;
HELENE, C .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1986, 83 (05) :1227-1231