A novel Fe(II)/α-ketoglutarate-dependent dioxygenase from Burkholderia ambifaria has β-hydroxylating activity of N-succinyl l-leucine

Lett Appl Microbiol. 2012 Dec;55(6):414-9. doi: 10.1111/j.1472-765X.2012.03308.x. Epub 2012 Oct 8.

Abstract

An Fe(II)/α-ketoglutarate-dependent dioxygenase, SadA, was obtained from Burkholderia ambifaria AMMD and heterologously expressed in Escherichia coli. Purified recombinant SadA had catalytic activity towards several N-substituted l-amino acids, which was especially strong with N-succinyl l-leucine. With the NMR and LC-MS analysis, SadA converted N-succinyl l-leucine into N-succinyl l-threo-β-hydroxyleucine with >99% diastereoselectivity. SadA is the first enzyme catalysing β-hydroxylation of aliphatic amino acid-related substances and a potent biocatalyst for the preparation of optically active β-hydroxy amino acids.

Keywords: Burkholderia ambifaria; Fe(II)/α‐ketoglutarate‐dependent dioxygenase; N‐substituted l‐amino acid β‐hydroxylase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Burkholderia / enzymology*
  • Burkholderia / genetics
  • Dioxygenases / genetics
  • Dioxygenases / metabolism*
  • Escherichia coli / genetics
  • Escherichia coli / metabolism*
  • Hydroxylation / genetics
  • Ketoglutaric Acids / chemistry
  • Ketoglutaric Acids / metabolism
  • Leucine / analogs & derivatives*
  • Leucine / biosynthesis*
  • Leucine / chemistry
  • Leucine / metabolism
  • Oxidation-Reduction
  • Succinates / chemistry
  • Succinates / metabolism*

Substances

  • Ketoglutaric Acids
  • Succinates
  • Dioxygenases
  • Leucine