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Highly Precise Shape Mimicry by a Difluorotoluene Deoxynucleoside, a Replication‐Competent Substitute for Thymidine
Author(s) -
Guckian Kevin M.,
Kool Eric T.
Publication year - 1997
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199728251
Subject(s) - thymidine , glycosidic bond , replication (statistics) , dna replication , dna , chemistry , hydrogen bond , stereochemistry , biology , biochemistry , molecule , organic chemistry , enzyme , virology
Large differences in the electrostatic properties of nucleosides can have surprisingly small effects on DNA replication. Size and shape appear to be more important, as structural studies of difluorotoluene deoxynucleoside 1 , an isostere of thymidine ( 2 ), prove. The two nucleosides have virtually the same aromatic ring, almost identical sugar puckers, and very similar glycosidic angles (see the structural formulas). Hydrogen‐bonding capacity is apparently not crucial for templating in DNA replication.