Formyl migration product of chanoclavine-I aldehyde in the presence of the old yellow enzyme FgaOx3 from Aspergillus fumigatus: a NMR structure elucidation

✍ Scribed by Xiulan Xie; Christiane Wallwey; Marco Matuschek; Klaus Steinbach; Shu-Ming Li

• Book ID: 102526038
• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 184 KB
• Volume: 49
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.2796

✦ Synopsis

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. Copyright © 2011 John Wiley & Sons, Ltd.