Metal-Modified Nucleobase Pairs and Triplets as Cytosine Receptors
✍ Scribed by Marc Sven Lüth; Eva Freisinger; Bernhard Lippert
- Publisher
- John Wiley and Sons
- Year
- 2001
- Tongue
- English
- Weight
- 222 KB
- Volume
- 7
- Category
- Article
- ISSN
- 0947-6539
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✦ Synopsis
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 4b, 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[alpha2PtAG]2+. The potential of modular, cationic receptors is illustrated.
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