title: Combined synthetic/CD strategy for the stereochemical assignment of the tricarballylic acid side chains of fumonisin B(1).
abstract: The circular dichroism (CD) exciton chirality method was employed for the stereochemical assignment of the tricarballylic acid (TCA) side chains of fumonisin B(1) 1a (FB(1)). Using 2-naphthoate for chromophoric derivatization of the reduced TCA moieties, the absolute configuration was shown to be R. For additional confirmation, an optically active dihydroxy-tert-butanoate 2 related to the TCA group of fumonisin B(1) was synthesized to serve as a model compound.
authors.affiliation: Lehrstuhl für Lebensmittelchemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany.
authors.forename: M
authors.initials: M
authors.lastname: Hartl
authors.forename: H U
authors.initials: HU
authors.lastname: Humpf
mesh_terms: D002264:Carboxylic Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002942:Circular Dichroism; D037341:Fumonisins; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008968:Molecular Conformation; D009183:Mycotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D013056:Spectrophotometry, Ultraviolet; D013237:Stereoisomerism; D014233:Tricarboxylic Acids / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D037341:Fumonisins; D007202:Indicators and Reagents; D009183:Mycotoxins; D014233:Tricarboxylic Acids; C056933:fumonisin B1; C028021:tricarballylic acid