REGIOSPECIFIC OXYGEN REARRANGEMENT IN REACTIONS OF THYMINE BROMOHYDRINS WITH NUCLEOPHILES USING BASES - FORMATION OF THYMINE EPOXIDE INTERMEDIATES

被引：20

作者：

RYANG, HS ^{[1
]}

WANG, SY ^{[1
]}

机构：

[1] JOHNS HOPKINS UNIV,SCH HYG & PUBL HLTH,DEPT ENVIRONM HLTH SCI,PROGRAM ENVIRONM CHEM,BALTIMORE,MD 21205

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1979年 / 44卷 / 07期

关键词：

D O I：

10.1021/jo01321a047

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

Studies of the reactions of trans-5-bromo-6-hydroxy-5, 6-dihydrothymines with nucleophiles in the presence of bases provide more definitive evidence for the formation of pyrimidine epoxide intermediates, which react readily with nucleophiles such as water, methanol, and N-acetyltyrosine ethyl ester to yield thymine glycol derivatives via regiospecific oxygen rearrangement, and suggest that such epoxides might cause an alternative type of nucleic acid-protein cross-linkage in biological systems. © 1979, American Chemical Society. All rights reserved.

引用

页码：1191 / 1192

页数：2

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