Enzymatic removal of carboxyl protecting groups. 1. Cleavage of the tert-butyl moiety

J Org Chem. 2005 Apr 29;70(9):3737-40. doi: 10.1021/jo050114z.

Abstract

[reaction: see text] A recent discovery that a certain amino acid motif (GGG(A)X-motif) in lipases and esterases determines their activity toward tertiary alcohols prompted us to investigate the use of these biocatalysts in the mild and selective removal of tert-butyl protecting groups in amino acid derivatives and related compounds. An esterase from Bacillus subtilis (BsubpNBE) and lipase A from Candida antarctica (CAL-A) were identified as the most active enzymes, which hydrolyzed a range of tert-butyl esters of protected amino acids (e.g., Boc-Tyr-O(t)Bu, Z-GABA-O(t)Bu, Fmoc-GABA-O(t)Bu) in good to high yields and left Boc, Z, and Fmoc-protecting groups intact.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acid Sequence
  • Amino Acids
  • Bacillus subtilis / enzymology*
  • Benzene Derivatives / metabolism*
  • Butanes / chemical synthesis
  • Butanes / metabolism
  • Candida albicans / enzymology*
  • Carboxylic Acids / metabolism
  • Catalysis
  • Esterases / metabolism*
  • Hydrocarbons, Halogenated / metabolism*
  • Indicators and Reagents
  • Lipase / metabolism*

Substances

  • Amino Acids
  • Benzene Derivatives
  • Butanes
  • Carboxylic Acids
  • Hydrocarbons, Halogenated
  • Indicators and Reagents
  • Esterases
  • Lipase