title: Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation.
abstract: A previous study showed that together with the festuclavine synthase FgaFS, the old yellow enzyme FgaOx3 from Aspergillus fumigatus catalyzed the conversion of chanoclavine-I aldehyde to festuclavine in the biosynthesis of ergot alkaloids. In the absence of FgaFS, a mixture containing two compounds with a ratio of 7:3 was detected in the enzyme assay of FgaOx3. NMR experiments including (DQF)-COSY, HSQC, HMBC and NOESY identified their structures as E/Z isomers of N-methyl-N-[(5R,10R)-10-(2-oxo-propyl)-2,4,5,10-tetrahydrobenzo[cd]indol-5-yl]formamide and proved the migration of the formyl group at C-8 in chanoclavine I-aldehyde to N-6 in the identified products.
authors: Xiulan
authors: X
authors: Xie
authors: Christiane
authors: C
authors: Wallwey
authors: Marco
authors: M
authors: Matuschek
authors: Klaus
authors: K
authors: Steinbach
authors: Shu-Ming
authors: SM
authors: Li
mesh_terms: D000447:Aldehydes / Q000737:chemistry / Q000378:metabolism*; D001232:Aspergillus fumigatus / Q000201:enzymology*; D055162:Biocatalysis; D004873:Ergolines / Q000737:chemistry / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy / Q000592:standards; D015394:Molecular Structure; D009252:NADPH Dehydrogenase / Q000378:metabolism*; D012015:Reference Standards; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D004873:Ergolines; C006959:chanoclavine; D009252:NADPH Dehydrogenase