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Title: Synthesis and regioselective deacylation studies on peracylated 2′-azido <i style="">arabino</i>- and <i style="">ribo</i>-thymine nucleosides: Towards 5′-<i style="">O</i>,2′-<i style="">N</i>-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
<i>Candida antarctica</i>
Issue Date: Dec-2009
Publisher: CSIR
Abstract: <smarttagtype namespaceuri="urn:schemas-microsoft-com:office:smarttags" name="place"> Peracylated 1-(2′-azido-<img src='/image/spc_char/alpha.gif' border=0>-L-arabino-/β-D-ribofuranosyl)thymine has been chemoenzymatically synthesized and subjected to deacylation studies in the presence of CAL-B (<i>Candida antarctica</i> 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′-<i style="">O</i>-acyl-<img src='/image/spc_char/alpha.gif' border=0>-L<sub></sub><smarttagtype namespaceuri="urn:schemas-microsoft-com:office:smarttags" name="place">-arabino / β-D-ribofuranosyl)thymine in very high yields, which are otherwise very difficult to prepare by classical chemical methods. The 3′-<i style="">O</i>-acylated azido-nucleosides may be used as key precursors for the preparation of 5′-<i style="">O</i>-2′-<i style="">N</i>-linked oligonucleotides of biological importance. </smarttagtype></smarttagtype>
Description: 1712-1720
ISSN: 0975-0983(Online); 0376-4699(Print)
Appears in Collections:IJC-B Vol.48B(12) December 2009]

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