title: Mutasynthesis of glycopeptide antibiotics: variations of vancomycin's AB-ring amino acid 3,5-dihydroxyphenylglycine.
abstract: In the mutasynthetic approach, the DeltadpgA mutant of the vancomycin-type glycopeptide antibiotic producer Amycolatopsis balhimycina, which is deficient in the synthesis of 3,5-dihydroxyphenylglycine (DPg), was supplemented with synthetic DPg analogues to obtain the corresponding modified glycopeptides. Sterically more demanding 3,5-disubstituted methoxy derivatives as well as monosubstituted DPg analogues were accepted as substrates. These facts indicate that steric and electronic requirements suffice in several cases for the oxidative closure of the AB ring, thus leading to the generation of novel antibiotically active glycopeptide derivatives. The results represent a further step in evaluating the potential of mutasynthesis for peptidic secondary metabolites.
authors.affiliation: Institute of Organic Chemistry, Auf der Morgenstelle 18, Germany.
authors.forename: Stefan
authors.initials: S
authors.lastname: Weist
authors.forename: Claudia
authors.initials: C
authors.lastname: Kittel
authors.forename: Daniel
authors.initials: D
authors.lastname: Bischoff
authors.forename: Bojan
authors.initials: B
authors.lastname: Bister
authors.forename: Volker
authors.initials: V
authors.lastname: Pfeifer
authors.forename: Graeme J
authors.initials: GJ
authors.lastname: Nicholson
authors.forename: Wolfgang
authors.initials: W
authors.lastname: Wohlleben
authors.forename: Roderich D
authors.initials: RD
authors.lastname: Süssmuth
mesh_terms: D039903:Actinobacteria / Q000235:genetics* / Q000378:metabolism*; D000900:Anti-Bacterial Agents / Q000096:biosynthesis* / Q000737:chemistry; D003470:Culture Media; D005998:Glycine / Q000031:analogs & derivatives* / Q000737:chemistry*; D006020:Glycopeptides / Q000096:biosynthesis* / Q000737:chemistry; D008968:Molecular Conformation; D009154:Mutation / Q000502:physiology*; D012118:Resorcinols / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization; D014640:Vancomycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000900:Anti-Bacterial Agents; D003470:Culture Media; D006020:Glycopeptides; D012118:Resorcinols; C087127:balhimycin; C079215:3,5-dihydroxyphenylglycine; D014640:Vancomycin; D005998:Glycine