Synthesis of deuterated gamma-lactones for use in stable isotope dilution assays |
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| Authors: | Hislop Jo-Anna Hunt Martin B Fielder Simon Rowan Daryl D |
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| Institution: | The Horticulture and Food Research Institute of New Zealand Ltd., Private Bag 11030, Palmerston North, New Zealand. |
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| Abstract: | Two syntheses of deuterated gamma-lactones for use as internal standards in stable isotope dilution assays (SIDA) were developed. 2,2,3,3-2H4]-gamma-Octa-, -gamma-deca-, and -gamma-dodecalactones with >89% deuterium incorporation were prepared in 27, 17, and 19% overall yields, respectively, by the reduction of a doubly protected hydroxypropiolic acid with deuterium gas. 3,3,4-2H3]-gamma-Octa- and -gamma-dodecalactones were prepared in 6 and 23% yields with >92% deuterium incorporation by the free radical addition of 2-iodoacetamide to 1,1,2-2H3]-1-hexene and 1,1,2-2H3]-1-decene, respectively. Reaction yields were highly dependent upon the purity of the 1-alkene starting material. The deuterated gamma-lactones were evaluated as internal standards for SIDA. |
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