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Title: Synthesis and regioselective deacylation studies on peracylated 2′-azido arabino- and ribo-thymine nucleosides: Towards 5′-O,2′-N-linked oligonucleotides
Authors: Sharma, Deepti
Khandelwal, Anuj
Sharma, Raman K
Bhatia, Sumati
Reddy, L Chandrashekar
Olsen, Carl E
Wengel, Jesper
Parmar, Virinder S
Prasad, Ashok K
Keywords: Nucleosides;Nucleosides;Candida antarctica;lipase-B;L-arabinose
Issue Date: Dec-2009
Publisher: CSIR
Abstract:  Peracylated 1-(2′-azido--L-arabino-/β-D-ribofuranosyl)thymine has been chemoenzymatically synthesized and subjected to deacylation studies in the presence of CAL-B (Candida antarctica lipase-B immobilized on polyacrylate) in acetonitrile. It is observed that CAL-B mediates highly selective deacylation of the ester function involving C-5′ hydroxyl group of the nucleosides leading to the formation of 1-(2′-azido-3′-O-acyl--L-arabino / β-D-ribofuranosyl)thymine in very high yields, which are otherwise very difficult to prepare by classical chemical methods. The 3′-O-acylated azido-nucleosides may be used as key precursors for the preparation of 5′-O-2′-N-linked oligonucleotides of biological importance.
Page(s): 1712-1720
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.48B(12) December 2009]

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