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RNA nucleosides as chiral sensing agents in NMR spectroscopy

Lokesh, N and Sachin, SL and Narendra, LV and Aruna, K and Suryaprakash, N (2015) RNA nucleosides as chiral sensing agents in NMR spectroscopy. In: ORGANIC & BIOMOLECULAR CHEMISTRY, 13 (26). pp. 7230-7235.

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Official URL: http://dx.doi.org/10.1039/c5ob00513b


The study reports chiral sensing properties of RNA nucleosides. Adenosine, guanosine, uridine and cytidine are used as chiral derivatizing agents to differentiate chiral 1 degrees-amines. A three component protocol has been adopted for complexation of nucleosides and amines. The chiral differentiating ability of nucleosides is examined for different amines based on the H-1 NMR chemical shift differences of diastereomers (Delta delta(R,S)). Enantiomeric differentiation has been observed at multiple chemically distinct proton sites. Adenosine and guanosine exhibit large chiral differentiation (Delta delta(R,S)) due to the presence of a purine ring. The diastereomeric excess (de) measured by using adenosine is in good agreement with the gravimetric values.

Item Type: Journal Article
Additional Information: Copy right for this article belongs to the ROYAL SOC CHEMISTRY, THOMAS GRAHAM HOUSE, SCIENCE PARK, MILTON RD, CAMBRIDGE CB4 0WF, CAMBS, ENGLAND
Department/Centre: Division of Chemical Sciences > NMR Research Centre (Formerly Sophisticated Instruments Facility)
Division of Chemical Sciences > Solid State & Structural Chemistry Unit
Date Deposited: 31 Jul 2015 13:55
Last Modified: 31 Jul 2015 13:55
URI: http://eprints.iisc.ac.in/id/eprint/51969

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