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Chlorimine formation and deamination of the model nucleobase 1‐methylcytosine
Author(s) -
BeyerlePfnür Rut,
Lippert Bernhard,
Schöllhorn Helmut,
Matischok Petra,
Thewalt Ulf
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230239
Subject(s) - chemistry , deamination , nucleobase , hypochlorous acid , uracil , 5 methylcytosine , chlorine , aqueous solution , stereochemistry , medicinal chemistry , organic chemistry , dna , biochemistry , enzyme , gene expression , dna methylation , gene
Treatment of the model nucleobase 1‐methylcytosine with chlorine in aqueous solution gives, depending on the reaction conditions, 5‐chloro‐1‐methylcytosine ( 3 ) or its hemiprotonated form 2 , 5,5‐dichloro‐6‐hyd‐roxy‐5,6‐dihydro‐4‐chlorimino‐1‐methylpyrimidin‐2‐one ( 5 ), and 5,5‐dichloro‐6‐hydroxy‐5,6‐dihydro‐1‐methyl‐uracil ( 4 ). While substitution of H5 of 1‐methylcytosine by chlorine giving 2 and 3 , and subsequent addition of hypochlorous acid to the 5,6‐double bond is not unexpected, chlorination of the exocyclic amino group 5 and deamination to give 4 is novel. The X‐ray structures of 4 and 5 are reported.