Expanding cyclitol structural diversity by biocatalysis and metalocatalysis. A click chemistry approach

Mol Divers. 2011 Feb;15(1):163-72. doi: 10.1007/s11030-010-9237-6. Epub 2010 Mar 3.

Abstract

The palladium catalyzed cross-coupling reaction of phenyltrifluoroborate with a chemoenzymatically derived bromoazidoconduritol, combined with 1,3-dipolar cycloaddition, with a variety of alkynes is described. Fourteen new compounds were synthesized in moderate to good yields. The click chemistry reaction can be effected by using sodium ascorbate and CuSO(4) · 5H(2)O as catalyst in toluene-H(2)O at room temperature.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biocatalysis*
  • Click Chemistry / methods*
  • Cyclitols / chemical synthesis
  • Cyclitols / chemistry*
  • Dioxygenases / metabolism
  • Palladium / chemistry*
  • Pseudomonas putida / enzymology

Substances

  • Cyclitols
  • Palladium
  • Dioxygenases