title: Isolation and Synthetic Diversification of Jadomycin 4-Amino-l-phenylalanine.
abstract: Streptomyces venezuelae ISP5230 was grown in the presence of phenylalanine analogues to observe whether they could be incorporated into novel jadomycin structures. It was found that the bacteria successfully produced jadomycins incorporating 4-aminophenylalanine enantiomers. Upon isolation and characterization of jadomycin 4-amino-l-phenylalanine (1), it was synthetically derivatized, using activated succinimidyl esters, to yield a small jadomycin amide library. These are the first examples of oxazolone-ring-containing jadomycins that have incorporated an amino functionality subsequently used for derivatization.
authors.forename: Camilo F
authors.initials: CF
authors.lastname: Martinez-Farina
authors.forename: Andrew W
authors.initials: AW
authors.lastname: Robertson
authors.affiliation: ‡Department of Chemistry, Acadia University, Wolfville, Nova Scotia, Canada.
authors.forename: Huimin
authors.initials: H
authors.lastname: Yin
authors.affiliation: ‡Department of Chemistry, Acadia University, Wolfville, Nova Scotia, Canada.
authors.forename: Susan
authors.initials: S
authors.lastname: Monro
authors.affiliation: ‡Department of Chemistry, Acadia University, Wolfville, Nova Scotia, Canada.
authors.forename: Sherri A
authors.initials: SA
authors.lastname: McFarland
authors.affiliation: §Institute for Marine Biosciences, National Research Council of Canada, Halifax, Nova Scotia, Canada.
authors.forename: Raymond T
authors.initials: RT
authors.lastname: Syvitski
authors.forename: David L
authors.initials: DL
authors.lastname: Jakeman
mesh_terms: D007546:Isoquinolines / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010081:Oxazolone / Q000737:chemistry; D010649:Phenylalanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013302:Streptomyces / Q000737:chemistry* / Q000254:growth & development
chemical_list: D007546:Isoquinolines; D009285:Naphthoquinones; C506597:jadomycin A; D010081:Oxazolone; C009722:4-aminophenylalanine; D010649:Phenylalanine