title: Synthesis of Inducamides A and B.
abstract: The inducamides are a family of chlorinated alkaloids featuring an amide arising from union of an l-tryptophan to a rare chlorosalicylic acid unit, the production of which is linked to a chemically induced mutation in the RNA polymerase of Streptomyces sp. (SNC-109-M3). The synthesis of inducamides A and B has been accomplished by the coupling of 6-hydroxy-3-chloro-2-methylbenzoic acid with l-6-chlorotryptophan and l-tryptophan, respectively, followed by ester hydrolysis. The spectroscopic data and optical rotation for each synthetic sample confirm the structures of these silent secondary metabolites and their biosynthesis from l-tryptophan.
authors.affiliation: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors.forename: Lydia M
authors.initials: LM
authors.lastname: Scott
authors.affiliation: School of Chemical Sciences, University of Auckland , 23 Symonds Street, Auckland, New Zealand.
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sperry
mesh_terms: D001565:Benzoates / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D013237:Stereoisomerism; D013302:Streptomyces / Q000235:genetics; D014364:Tryptophan / Q000378:metabolism
chemical_list: D001565:Benzoates; D026121:Indole Alkaloids; C000594876:inducamide A; C000594877:inducamide B; C000610092:methyl 3-chloro-6-methoxy-2-methylbenzoate; D014364:Tryptophan