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Metal-modified nucleobase pairs and triplets as cytosine receptors


Lüth, M S; Freisinger, Eva; Lippert, Bernhard (2001). Metal-modified nucleobase pairs and triplets as cytosine receptors. Chemistry - A European Journal, 7(10):2104-2113.

Abstract

A preorganized cationic receptor 2 for cytosine (C) is described which is composed of trans-a2PtII (a=NH3 or CH3NH2) 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 1H 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-[a2PtAG]2+. The potential of modular, cationic receptors is illustrated.

Abstract

A preorganized cationic receptor 2 for cytosine (C) is described which is composed of trans-a2PtII (a=NH3 or CH3NH2) 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 1H 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-[a2PtAG]2+. The potential of modular, cationic receptors is illustrated.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Language:English
Date:2001
Deposited On:18 Apr 2013 08:55
Last Modified:05 Apr 2016 16:40
Publisher:Wiley-VCH Verlag Berlin
ISSN:0947-6539
Publisher DOI:https://doi.org/10.1002/1521-3765(20010518)7:10<2104::AID-CHEM2104>3.0.CO;2-F

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