|
NISCAIR ONLINE PERIODICALS REPOSITORY (NOPR) >
NISCAIR PUBLICATIONS >
Research Journals >
Indian Journal of Chemistry -Section B (IJC-B) >
IJC-B Vol.48B [2009] >
IJC-B Vol.48B(12) December 2009] >
| 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) |
| Source: | IJC-B Vol.48B(12) December 2009]
|
|
