Biosynthesis and structural revision of neomarinone.
[reaction: see text] The biosynthesis of the meroterpenoid neomarinone from a marine actinomycete was probed through feeding experiments with (13)C-labeled precursors. NMR characterization of [U-(13)C(6)]glucose-enriched neomarinone led to the structural revision of structure 4a to 4b, which was confirmed by extensive 2D NMR spectrometry with unlabeled compound.
College of Pharmacy and the Department of Chemistry, University of Arizona, Tucson, Arizona 85721, USA.
John A
JA
Kalaitzis
Yoshimitsu
Y
Hamano
George
G
Nilsen
Bradley S
BS
Moore
D001203:Ascomycota / Q000378:metabolism; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis* / Q000737:chemistry
D005663:Furans; D009285:Naphthoquinones; C493875:neomarinone