On the biosynthetic origin of methoxymalonyl-acyl carrier protein, the substrate for incorporation of "glycolate" units into ansamitocin and soraphen A

J Am Chem Soc. 2006 Nov 8;128(44):14325-36. doi: 10.1021/ja064408t.

Abstract

Feeding experiments with isotope-labeled precursors rule out hydroxypyruvate and TCA cycle intermediates as the metabolic source of methoxymalonyl-ACP, the substrate for incorporation of "glycolate" units into ansamitocin P-3, soraphen A, and other antibiotics. They point to 1,3-bisphosphoglycerate as the source of the methoxymalonyl moiety and show that its C-1 gives rise to the thioester carbonyl group (and hence C-1 of the "glycolate" unit), and its C-3 becomes the free carboxyl group of methoxymalonyl-ACP, which is lost in the subsequent Claisen condensation on the type I modular polyketide synthases (PKS). d-[1,2-(13)C(2)]Glycerate is also incorporated specifically into the "glycolate" units of soraphen A, but not of ansamitocin P-3, suggesting differences in the ability of the producing organisms to activate glycerate. A biosynthetic pathway from 1,3-bisphosphoglycerate to methoxymalonyl-ACP is proposed. Two new syntheses of R- and S-[1,2-(13)C(2)]glycerol were developed as part of this work.

Publication types

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

MeSH terms

  • Acyl Carrier Protein / biosynthesis*
  • Acyl Carrier Protein / chemistry
  • Amino Acid Sequence
  • Carbon Isotopes
  • Citric Acid Cycle / physiology
  • Diphosphoglyceric Acids / chemistry
  • Diphosphoglyceric Acids / metabolism
  • Glycolates / chemistry*
  • Isotope Labeling
  • Macrolides / chemistry
  • Macrolides / metabolism*
  • Malonates / chemistry*
  • Maytansine / analogs & derivatives*
  • Maytansine / chemistry
  • Maytansine / metabolism
  • Models, Chemical
  • Molecular Sequence Data
  • Polyketide Synthases / chemistry
  • Polyketide Synthases / metabolism
  • Pyruvates / metabolism

Substances

  • Acyl Carrier Protein
  • Carbon Isotopes
  • Diphosphoglyceric Acids
  • Glycolates
  • Macrolides
  • Malonates
  • Pyruvates
  • glycolic acid
  • soraphen A
  • Maytansine
  • glycerate 1,3-biphosphate
  • ansamitocins
  • Polyketide Synthases
  • hydroxypyruvic acid
  • malonic acid