Polypropionate biosynthesis

Cutignano, A., Cimino, G Villani, G., and Fontana, A. (2009) Origin of the Cj-unit in placidenes further insights into tax divergence of polypropionates biosynthesis in marine molluscs and fungi, Fusaripyrones. Tetrahedron, 65, 8161-8164. 

Manker, D. C., Garson, M. J., and Faulkner, D. J., De novo biosynthesis of polypropionate metabolites in the marine pulmonate Siphonaria denticulata, J. Chem. Soc. Chem. Commun., 1061, 1988. 

Biosynthesis of y-Pyrone-Containing Polypropionate Natural Products... 

Paterson I, Scott JJ. Laboratory emulation of polyketide biosynthesis an iretive, aldod-based, synthetic entry to polyketide libraries using (R)- and (S)-l-benzyloxy)-2-methylpentan-3-one, and conformational aspects of extended polypropionates. Chem. Soc. Perkin Trans. I. 1999 1003-1014. 

Hydroxy-8-lactone such as 209 constitutes the structural motif of natural polypropionates and an intermediate in the step-by-step biosynthesis of these compounds. As shown in Scheme 22.34, 209 is readily obtained by diaster-eoselective reduction of ketone 202, followed by ozonolysis of its enol ester moiety. ... 

Fontana, A., Cutignano, A., Giordano, A., Domtoech Coll, A., and Cimino, G. (2004) Biosynthesis of aglajnes, polypropionate allomones of the opistobranch mollusc Bulla striata. Tetrahedron Lett., 45, 6847-6850. 

The biosynthesis of polypropionates is similar to that of polyketides, acetylcoenzyme A being replaced by propio-nylcoenzyme A, the autocondensation of which produces methylmalonylcoenzyme A this then condenses with a second molecule of propionylcoenzyme A, and so on." The traditional acylpolymalonate pathway turns into an acylpolymethylmalonate pathway, which was confirmed in sacoglossans Cyerce sp.) and pulmonates (Siphonaria sp.) by incorporation of [l- C] and [2- C] propionate (Cimino and Sodano, 1993 Garson, 1989, 1993 Cimino et al., 2004). 

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