ISSN:
0018-019X
Keywords:
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
On the Biosynthesis of γ-Dodecanolactone in Ripening Fruits: Flavor Constituents from Strawberries (Fragaria ananassa) and Peaches (Prunus persica)Administration of deuterium-labelled 9,10-expoxy[8,8-2H2]heptadecanoic acid 8a/b and 9,10-dihydroxy-[8,8-2H2]methylheptadecanoate 9 as lower analogues of oleic acid 1 to ripening fruits of strawberries (Fragaria ananassa) and peaches (Prunus persica) results in the emission of labelled γ-undecanolactone (5) as the lower analog of γ-dodecanolactone (2). The transformation proceeds with loss of a single D-atom from C(8) of the precursors. Early precursors, like the C17-epoxy-acids 8a/b yield (4R)-γ-undecanolactone (5) of high enantiomeric purity, while later intermediates results in (4R)-γ-undecanolactone (5) of low purity. The data support a biosynthetic sequence involving the consecutive action of an epoxide hydrolase and β-oxidation to generate the correct chain length of the lactone percursor. The final steps proceed via cyclization of the 3,4-dihydroxyundecanoic acid 13 to the 3-hydroxy-γ-undecanolactone 14. Elimination of H2O and reduction of the intermediate γ-undec-2-enolactone 15 terminate the biosynthesis of 5. The sequence is representative for the biosynthesis of naturally occurring γ-dodecanolactone (2).
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/hlca.19950780406
