title: Eight-membered ring-containing jadomycins: implications for non-enzymatic natural products biosynthesis.
abstract: Jadomycin Oct (1) was isolated from Streptomyces venezuelae ISP5230 and characterized as a structurally unique eight-membered l-ornithine ring-containing jadomycin. The structure was elucidated through the semisynthetic derivatization of starting material via chemoselective acylation of the l-ornithine α-amino group using activated succinimidyl esters. Incorporation of 5-aminovaleric acid led to jadomycin AVA, a second eight-membered ring-containing jadomycin. These natural products illustrate the structural diversity permissible from a non-enzymatic step within a biosynthetic pathway and exemplifies the potential for discovery of novel scaffolds.
authors.affiliation: Department of Chemistry and ⊥College of Pharmacy, Dalhousie University , Halifax, Nova Scotia B3H 4R2, Canada.
authors.forename: Andrew W
authors.initials: AW
authors.lastname: Robertson
authors.forename: Camilo F
authors.initials: CF
authors.lastname: Martinez-Farina
authors.forename: Deborah A
authors.initials: DA
authors.lastname: Smithen
authors.forename: Huimin
authors.initials: H
authors.lastname: Yin
authors.forename: Susan
authors.initials: S
authors.lastname: Monro
authors.forename: Alison
authors.initials: A
authors.lastname: Thompson
authors.forename: Sherri A
authors.initials: SA
authors.lastname: McFarland
authors.forename: Raymond T
authors.initials: RT
authors.lastname: Syvitski
authors.forename: David L
authors.initials: DL
authors.lastname: Jakeman
mesh_terms: D000215:Acylation; D021542:Amino Acids, Neutral / Q000737:chemistry; D000970:Antineoplastic Agents / Q000737:chemistry / Q000494:pharmacology*; D001688:Biological Products / Q000138:chemical synthesis / Q000737:chemistry*; D045744:Cell Line, Tumor / Q000187:drug effects; D004354:Drug Screening Assays, Antitumor; D005285:Fermentation; D006576:Heterocyclic Compounds, 4 or More Rings / Q000737:chemistry* / Q000302:isolation & purification / Q000378:metabolism; D006801:Humans; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009952:Ornithine / Q000737:chemistry; D013302:Streptomyces / Q000254:growth & development / Q000378:metabolism*; D013329:Structure-Activity Relationship; D053719:Tandem Mass Spectrometry
chemical_list: D021542:Amino Acids, Neutral; D000970:Antineoplastic Agents; D001688:Biological Products; D006576:Heterocyclic Compounds, 4 or More Rings; C013809:5-aminovaleric acid; D009952:Ornithine