Biosynthetic considerations of triscatechol siderophores framed on serine and threonine macrolactone scaffolds

Metallomics. 2017 Jul 19;9(7):824-839. doi: 10.1039/c7mt00111h.

Abstract

Bacteria often produce siderophores to facilitate iron uptake. One of the most studied siderophores is enterobactin, the macrolactone trimer of 2,3-dihydroxybenzoyl-l-serine, produced by E. coli and many other enteric bacteria. Other siderophores are variants of enterobactin, with structural modifications including expansion of the tri-serine core to a tetra-serine macrolactone, substitution of l-serine with l-threonine, insertion of amino acids (i.e., Gly, l-Ala, d-Lys, d- and l-Arg, l-Orn), catechol glucosylation, and linearization of the tri-serine macrolactone core. In this review we summarize the current understanding of the biosyntheses of these enterobactin variants, placing them in contrast with the well-established biosynthesis of enterobactin.

Publication types

  • Review
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Amino Acid Sequence
  • Catechols / chemistry
  • Catechols / metabolism*
  • Enterobactin / chemistry
  • Enterobactin / metabolism
  • Lactones / metabolism*
  • Serine / metabolism*
  • Siderophores / chemistry
  • Siderophores / metabolism*
  • Threonine / metabolism*

Substances

  • Catechols
  • Lactones
  • Siderophores
  • Enterobactin
  • Threonine
  • Serine
  • catechol