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Stereoselectivity, Sequence Specificity and Mechanism of Action of the Azinomycin Epoxide
Author(s) -
DavidCordonnier MarieHélène,
CaselyHayford Maxwell,
Kouach Mostafa,
Briand Gilbert,
Patterson Laurence H.,
Bailly Christian,
Searcey Mark
Publication year - 2006
Publication title -
chembiochem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.05
H-Index - 126
eISSN - 1439-7633
pISSN - 1439-4227
DOI - 10.1002/cbic.200600244
Subject(s) - depurination , epoxide , diastereomer , chemistry , stereoselectivity , stereochemistry , guanine , alkylation , sequence (biology) , natural product , biochemistry , dna , nucleotide , catalysis , gene
Not like the rest . In this study we show that the four diastereomers of the azinomycin epoxide ( 1 ) have different sequence selectivities, while the natural product appears to exert its effects through reversible N 7 alkylation of guanine followed by irreversible depurination (see scheme).