These tools will no longer be maintained as of December 31, 2024. Archived website can be found here. PubMed4Hh GitHub repository can be found here. Contact NLM Customer Service if you have questions.


PUBMED FOR HANDHELDS

Search MEDLINE/PubMed


  • Title: Enzymatic regioselective levulinylation of 2'-deoxyribonucleosides and 2'-o-methylribonucleosides.
    Author: Lavandera I, García J, Fernández S, Ferrero M, Gotor V, Sanghvi YS.
    Journal: Curr Protoc Nucleic Acid Chem; 2005 Jul; Chapter 2():Unit 2.11. PubMed ID: 18428939.
    Abstract:
    The levulinyl-protected nucleosides are key building blocks for the solution-phase synthesis of oligonucleotides. Short and efficient syntheses of 3'- and 5'-O-levulinylated 2'-deoxyribonucleosides and 2'-O-methylribonucleosides have been developed from the corresponding nucleosides by enzyme-catalyzed regioselective acylation in organic solvents or from 3',5'-di-O-levulinyl derivatives by regioselective enzymatic hydrolysis. Lipase-mediated levulinylation of various nucleosides has been accomplished with acetonoxime levulinate as an acyl donor. Use of immobilized Pseudomonas cepacia lipase (PSL-C) has furnished 3'-O-levulinylated 2'-deoxyribonucleosides in excellent yields. Similarly, Candida antarctica lipase B (CAL-B) has provided 5'-O-levulinylated nucleosides in high yields. 3'-O-Levulinylated 2'-deoxyribonucleosides and 2'-O-methylribonucleosides were prepared via selective hydrolysis of 3',5'-di-O-levulinate esters using CAL-B.
    [Abstract] [Full Text] [Related] [New Search]