Yeast cystathionine beta-synthase reacts with L-allothreonine, a non-natural substrate, and L-homocysteine to form a new amino acid, 3-methyl-L-cystathionine

Biochemistry. 2002 Feb 12;41(6):1828-35. doi: 10.1021/bi011756t.

Abstract

Our studies of the reaction mechanism of cystathionine beta-synthase from yeast (Saccharomyces cerevisiae) are facilitated by the spectroscopic properties of the pyridoxal phosphate coenzyme. The enzyme catalyzes the reaction of L-serine with L-homocysteine to form L-cystathionine through a series of pyridoxal phosphate intermediates. In this work, we explore the substrate specificity of the enzyme by use of substrate analogues combined with kinetic measurements under pre-steady-state conditions and with circular dichroism and fluorescence spectroscopy under steady-state conditions. Our results show that L-allothreonine, but not L-threonine, serves as an effective substrate. L-Allothreonine reacts with the pyridoxal phosphate cofactor to form a stable 3-methyl aminoacrylate intermediate that absorbs maximally at 446 nm. The rapid-scanning stopped-flow results show that the binding of L-allothreonine as the external aldimine is faster than formation of the 3-methyl aminoacrylate intermediate. The 3-methyl aminoacrylate intermediate reacts with L-homocysteine to form a new amino acid, 3-methyl-L-cystathionine, which was characterized by nuclear magnetic resonance spectroscopy. This new amino acid may be a useful analogue of L-cystathionine.

Publication types

  • Comparative Study
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Circular Dichroism
  • Cystathionine / analogs & derivatives
  • Cystathionine / biosynthesis*
  • Cystathionine / chemistry
  • Cystathionine beta-Synthase / metabolism*
  • Homocysteine / chemistry
  • Homocysteine / metabolism
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Pyridoxal Phosphate / metabolism
  • Saccharomyces cerevisiae / enzymology*
  • Serine / metabolism
  • Spectrophotometry
  • Substrate Specificity
  • Threonine / analogs & derivatives
  • Threonine / chemistry
  • Threonine / metabolism

Substances

  • 3-methylcystathionine
  • Homocysteine
  • Threonine
  • Cystathionine
  • Serine
  • Pyridoxal Phosphate
  • Cystathionine beta-Synthase