Characterization of primary fatty amides produced by lipase-catalyzed amidation of hydroxylated fatty acids |
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Authors: | William?E?Levinson Email author" target="_blank">Tsung?Min KuoEmail author David?Weisleder |
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Affiliation: | (1) New Crops and Processing Technology Research Units, NCAUR, ARS, USDA, 61604 Peoria, Illinois;(2) Microbial Genomics and Bioprocessing Research Unit, USDA-ARS-NCAUR, 1815 N. University St., 61604 Peoria, IL |
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Abstract: | A novel hydroxylated primary fatty amide was produced from lesquerolic acid by direct amidation with ammonia catalyzed by
immobilized Pseudozyma (Candida) antarctica lipase B (Novozym 435) in organic solvent. The amides of ricinoleic acid and oleic acid were also produced for comparison.
The hydroxy FA were transformed at comparable rates to that of oleic acid. The rate of amide formation was greater for the
longerchain lesquerolic acid than for ricinoleic acid. All products exhibited characteristic primary-amide mass spectrum peaks
with a base peak at m/z 59 and a strong ion fragment at m/z 72. Other peaks present are consistent with cleavage on either side of the hydroxyl position. The mass spectra, together
with 1H and 13C NMR data, suggest that the products of lipase-catalyzed direct amidation of ricinoleic acid and lesquerolic acid are 12-hydroxy-9(Z)-octadecenamide and 14-hydroxy-11(Z)-eicosenamide, respectively. |
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Keywords: | Hydroxy fatty acids hydroxy fatty amides lipase-catalyzed amidation structural analysis transformation |
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