Premium
Metal‐Modified Nucleobase Pairs and Triplets as Cytosine Receptors
Author(s) -
Lüth Marc Sven,
Freisinger Eva,
Lippert Bernhard
Publication year - 2001
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/1521-3765(20010518)7:10<2104::aid-chem2104>3.0.co;2-f
Subject(s) - thymine , cytosine , nucleobase , guanine , uracil , chemistry , stereochemistry , hydrogen bond , adduct , crystallography , cationic polymerization , dna , receptor , molecule , ligand (biochemistry) , molecular structure of nucleic acids: a structure for deoxyribose nucleic acid , base pair , nucleotide , biochemistry , organic chemistry , gene
A preorganized cationic receptor 2 for cytosine (C) is described which is composed of trans ‐a 2 Pt II (a=NH 3 or CH 3 NH 2 ) cross‐linked modules with adenine (A), guanine (G), and uracil (U) or thymine (T) model nucleobases. The functions of these three modules are as follows: i) Adenine orientates the two other bases at right angles, thus producing the L‐shape of the receptor. ii) Guanine is the primary receptor. iii) Uracil or thymine act as coreceptors. Compared with the normal Watson–Crick pair between G and C, the association constant between 2 and C increases by a factor of 3 (in DMSO). As deduced from 1 H NMR spectroscopy and confirmed by the X‐ray crystal structure of the C adduct 4 b , cytosine is fixed through five hydrogen bonds to the receptor, one of which involves the aromatic H(5) of C. A comparison of C binding is made with a structurally related linkage isomer receptor as well as the precursor molecule trans ‐[a 2 PtAG] 2+ . The potential of modular, cationic receptors is illustrated.