First biosynthetic evidence on the phenyl-containing polyketides of the marine mollusc Scaphander lignarius.
The biosynthesis of lignarenones 1 and 2, the major polyketides of the Mediterranean mollusc Scaphander lignarius is described. The process is primed by benzoic acid and requires acetate and propionate as extender units. The labeling pattern suggests PKS-like synthesis of an unusual E,Z,E-triene chain and origin of the benzoate unit from phenylalanine. 13C-13C NMR COSY has been used to establish the labeling positions due to incorporation of 13C2-acetate.
Instituto di Chimica Biomolecolare, CNR, Pozzuoli, Naples, italy.
Adele
A
Cutignano
Conxita
C
Avila
Anna
A
Domenech-Coll
Giuliana
G
d'Ippolito
Guido
G
Cimino
Angelo
A
Fontana
D000818:Animals; D008386:Marine Biology; D008974:Mollusca / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D048630:Polyketide Synthases / Q000378:metabolism; D013237:Stereoisomerism
D011090:Polyenes; C530920:lignarenone A; C079197:lignarenone B; D048630:Polyketide Synthases