STUDIES ON 6-METHYL-5-DEAZATETRAHYDROPTERIN AND ITS 4A ADDUCTS

被引：45

作者：

MOAD, G ^{[1
]}

LUTHY, CL ^{[1
]}

BENKOVIC, PA ^{[1
]}

BENKOVIC, SJ ^{[1
]}

机构：

[1] PENN STATE UNIV,DEPT CHEM,UNIVERSITY PK,PA 16802

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1979年 / 101卷 / 20期

关键词：

D O I：

10.1021/ja00514a033

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The oxidation properties of 6-methyl-5-deazatetrahydropterin (2) have been examined. The compound (2) reacts with a variety of electrophilic reagents (including A’-halosuccinimide, bromine, peroxy acid, and singlet oxygen) to generate the corresponding 4a adduct. These adducts (3-6) are characterized by their spectral properties (1H and 13C NMR, UV) and analytical data. The aqueous-solution chemistry of the adducts is a function of the nature of the 4a substituent. The bromo and chloro adducts are readily reduced (and the former compound is an active brominating agent), while the hydroxy adduct undergoes a facile decomposition with rupture of the pyrimidine ring. The compound 2 is a competitive inhibitor of both phenylalanine and tyrosine hydroxylases, whereas the 4a adducts (3-6) show no apparent interaction with the enzyme. © 1979, American Chemical Society. All rights reserved.

引用

页码：6068 / 6076

页数：9

共 44 条

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