Pentalenolactone biosynthesis

Eleven of the CYPs from S. avermitilis were located in known gene clusters involved in secondary metabolism, including that of geosmin, avermectin, filipin, and pentalenolactone biosynthesis, and again, as in S. coelicolor, others appear to be involved in uncharacterized pathways of secondary metabolism. CYP178A1 is in a cluster with a nomibosomal peptide synthase, CYP107Y1 and CYP 181A1 are associated with a T5q>e n... 

Quaderer R, Omura S, Ikeda H, Cane DE (2006) Pentalenolactone biosynthesis. Molecular cloning and assignment of biochemical function to PtII, a cytochrome P450 of Streptomyces avermitilis. J Am Chem Soc 128 13036-13037... 

The pentalane class of sesquiterpenoids has received substantial attention in the past year from the standpoints of structural elucidation, biosynthesis, and synthesis. Two new metabolites of this class are pentalenic acid (298) and pentalenolactone H (299). Both these compounds have a secondary hydroxyl function adjacent to the gem-dimethyl group and are thus potential precursors of pentalenolactone (300) in which one of these methyl groups has undergone a 1,2-migration. Cane and Rossi " have now identified a further metabolite of a Streptomyces strain which has been named pentalenolactone E (301) and is now... 

Paquette et a/.182 have accomplished a relatively short synthesis of the methyl ester of pentalenolactone E (372) (Scheme 43). Full details of the biosynthesis of pentalenolactone (373) from [t/-13C6] glucose and [6,6-2H2] glucose have been reported.183 These substrates were used in view of the lack of incorporation of the more conventional acetate and mevalonate isoprenoid precursors. The stereochemical picture which has emerged from this study is that the pentalenane... 

Seto, H., T. Sasaki, H. Yonehara, and J. Uzawa Studies on the Biosynthesis of Pentalenolactone. Part I. Apphcation of Longrange Selective Proton Decoupling (LSPD) and Selective C- H NOE in the Structure Elucidation of Pentalenolactone G. Tetrahedron Letters 923 (1978). 

Seto H, Sasaki T, Yonehara H, Uzawa J 1978 Studies on the biosynthesis of pentalenolactone. Part I. Application of long range selective proton decoupling (LSPD) and selective C-[ Hj NOE in the structural elucidation of pentalenolactone G. Tetrahedron Lett 923 - 926... 

This technique was first used to study the sesquiterpene antibiotic pentalenolactone Cane, D E., T. Rossi, and J. P. Pachlatko The Biosynthesis of Pentalenolactone. Tetrahedron Letters, 3639 (1979). 

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