2. Academic Validation
  3. Chemoenzymatic convergent synthesis of 2'-O,4'-C-methyleneribonucleosides

Chemoenzymatic convergent synthesis of 2'-O,4'-C-methyleneribonucleosides

  • J Org Chem. 2014 Jul 3;79(13):6336-41. doi: 10.1021/jo5008338.
Vivek K Sharma 1,  Manish Kumar,  Carl E Olsen,  Ashok K Prasad
Affiliations

Affiliation

  • 1 Bioorganic Laboratory, Department of Chemistry, University of Delhi , Delhi 110 007, India.
PMID: 24901539 DOI: 10.1021/jo5008338
Abstract

Novozyme-435-catalyzed efficient regioselective acetylation of one of the two diastereotopic hydroxymethyl functions in 3-O-benzyl-4-C-hydroxymethyl-1,2-O-isopropylidene-α-d-ribofuranose has been achieved. The enzymatic methodology has been successfully utilized for convergent synthesis of bicyclic nucleosides (LNA monomers) T, U, A, and C. Further, it has been demonstrated that Novozyme-435 can be used for 10 cycles of the acylation reaction without losing selectivity and efficiency.

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