Generation of new landomycins by combinatorial biosynthetic manipulation of the LndGT4 gene of the landomycin E cluster in S. globisporus

Chem Biol. 2004 Apr;11(4):547-55. doi: 10.1016/j.chembiol.2004.03.011.

Abstract

A 3 kb DNA fragment from the Streptomyces globisporus 1912 landomycin E (LaE) biosynthetic gene cluster (lnd) was completely sequenced. Three open reading frames were identified, lndGT4, lndZ4, and lndZ5, whose probable translation products resemble a glycosyltransferase, a reductase, and a hydroxylase, respectively. Studies of generated mutants from disruption and complementation experiments involving the lndGT4 gene allowed us to determine that LndGT4 controls the terminal L-rhodinose sugar attachment during LaE biosynthesis and that LndZ4/LndZ5 are responsible for the unique C11-hydroxylation of the landomycins. Generation of the novel landomycins F, G, and H in the course of these studies provided evidence for the flexibility of lnd glycosyltransferases toward their acceptor substrates and a basis for initial structure-activity relationships within the landomycin family of antibiotics.

Publication types

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

MeSH terms

  • Aminoglycosides / biosynthesis*
  • Aminoglycosides / chemistry*
  • Aminoglycosides / pharmacology
  • Antineoplastic Agents / chemistry
  • Antineoplastic Agents / pharmacology
  • Cell Division / drug effects
  • Cell Line, Tumor
  • Glycosyltransferases / analysis
  • Glycosyltransferases / genetics*
  • Glycosyltransferases / metabolism
  • Humans
  • Mixed Function Oxygenases / analysis
  • Mixed Function Oxygenases / genetics
  • Mixed Function Oxygenases / metabolism
  • Molecular Sequence Data
  • Multigene Family
  • Mutation
  • Oxidoreductases / analysis
  • Oxidoreductases / genetics
  • Oxidoreductases / metabolism
  • Streptomyces / enzymology
  • Streptomyces / genetics*
  • Streptomyces / metabolism
  • Structure-Activity Relationship

Substances

  • Aminoglycosides
  • Antineoplastic Agents
  • landomycin D
  • landomycin E
  • landomycin F
  • landomycin G
  • landomycin H
  • Mixed Function Oxygenases
  • Oxidoreductases
  • Glycosyltransferases

Associated data

  • GENBANK/AY443343
  • GENBANK/AY443344
  • GENBANK/AY443345
  • GENBANK/AY523868
  • GENBANK/AY528820