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Direct Observation of a Cytosine Analogue that Forms Five Hydrogen Bonds to Guanosine: Guanidino G‐Clamp
Author(s) -
Wilds Christopher J.,
Maier Martin A.,
Tereshko Valentina,
Manoharan Muthiah,
Egli Martin
Publication year - 2002
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/1521-3773(20020104)41:1<115::aid-anie115>3.0.co;2-r
Subject(s) - guanosine , hydrogen bond , chemistry , cytosine , crystallography , stereochemistry , guanine , clamp , crystal structure , dna , base pair , molecule , nucleotide , biochemistry , computer science , organic chemistry , gene , clamping , computer vision
Bound and clamped : A novel heterocyclic base modification, the guanidino G‐clamp, is designed to allow two Hoogsteen‐type hydrogen bonds to form between the amino and imino nitrogen atoms of a tethered guanidinium group to O6 and N7 of guanosine, which results in a total of five hydrogen bonds (broken lines, see picture). Details of a crystal structure at 1.0‐Å resolution of a modified DNA decamer containing this guanidino G‐clamp analogue demonstrate its mechanism of binding.