N5-phosphonoacetyl-L-ornithine (PALO): a convenient synthesis and investigation of influence on regulation of amino acid biosynthetic genes in Saccharomyces cerevisiae

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2351-3. doi: 10.1016/j.bmcl.2011.02.081. Epub 2011 Feb 26.

Abstract

A scalable four-step synthesis of the ornithine transcarbamylase inhibitor N(5)-phosphonoacetyl-l-ornithine (PALO) is achieved through boroxazolidinone protection of ornithine. Investigations in the model organism Saccharomyces cerevisiae found that, in contrast to a previous report, PALO did not influence growth rate or expression of genes involved in arginine metabolism.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Arginine / metabolism*
  • Gene Expression Regulation
  • Ornithine / analogs & derivatives*
  • Ornithine / chemical synthesis
  • Ornithine / chemistry
  • Ornithine / pharmacology
  • Ornithine Carbamoyltransferase / antagonists & inhibitors
  • Ornithine Carbamoyltransferase / metabolism
  • Saccharomyces cerevisiae / drug effects
  • Saccharomyces cerevisiae / metabolism*
  • Saccharomyces cerevisiae Proteins / genetics
  • Saccharomyces cerevisiae Proteins / metabolism*

Substances

  • Saccharomyces cerevisiae Proteins
  • N(delta)-(phosphonoacetyl)-L-ornithine
  • Arginine
  • Ornithine
  • Ornithine Carbamoyltransferase