5455-97-0Relevant articles and documents
Enzyme Cascade Reactions for the Biosynthesis of Long Chain Aliphatic Amines from Renewable Fatty Acids
Lee, Da-Som,Song, Ji-Won,Vo?, Moritz,Schuiten, Eva,Akula, Ravi Kumar,Kwon, Yong-Uk,Bornscheuer, Uwe,Park, Jin-Byung
, (2019)
Enzyme cascade reactions for the synthesis of long chain aliphatic amines such as (Z)-12-aminooctadec-9-enoic acid, 10- or 12-aminooctadecanoic acid, and 10-amino-12-hydroxyoctadecanoic acid from renewable fatty acids were investigated. (Z)-12-aminooctadec-9-enoic acid was produced from ricinoleic acid ((Z)-12-hydroxyoctadec-9-enoic acid) via (Z)-12-ketooctadec-9-enoic acid with a conversion of 71% by a two-step in vivo biotransformation involving a long chain secondary alcohol dehydrogenase (SADH) from Micrococcus luteus and a variant of the amine transaminase (ATA) from Vibrio fluvialis. 10-Aminooctadecanoic acid was prepared from oleic acid ((Z)-octadec-9-enoic acid) via 10-hydroxyoctadecanoic acid and 10-ketooctadecanoic acid by an in vivo three-step biocatalysis reaction involving not only the SADH and ATA variants, but also a fatty acid double bond hydratase (OhyA) from Stenotrophomonas maltophilia. 10-Aminooctadecanoic acid was produced at a total rate of 4.4 U/g dry cells with a conversion of 87% by recombinant Escherichia coli expressing the SADH and ATA variants, and OhyA simultaneously. In addition, bulky aliphatic amines could also be produced by the isolated enzymes (i. e., the SADH, the ATA variants, and a nicotinamide adenine dinucleotide (NADH) oxidase from Lactobacillus brevis) with methylbenzylamine or benzylamine as amino donor. This study thus contributes to the biosynthesis of long chain aliphatic amines having two large substituents next to the amine functionality. (Figure presented.).
Characterization of hydroxy fatty acid dehydrogenase involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a
Takeuchi, Michiki,Kishino, Shigenobu,Park, Si-Bum,Kitamura, Nahoko,Ogawa, Jun
, p. 7 - 12 (2015/05/13)
Hydroxy fatty acid dehydrogenase, which is involved in polyunsaturated fatty acid saturation metabolism in Lactobacillus plantarum AKU 1009a, was cloned, expressed, purified, and characterized. The enzyme preferentially catalyzed NADH-dependent hydrogenation of oxo fatty acids over NAD+-dependent dehydrogenation of hydroxy fatty acids. In the dehydrogenation reaction, fatty acids with an internal hydroxy group such as 10-hydroxy-cis-12-octadecenoic acid, 12-hydroxy-cis-9-octadecenoic acid, and 13-hydroxy-cis-9-octadecenoic acid served as better substrates than those with α- or β-hydroxy groups such as 3-hydroxyoctadecanoic acid or 2-hydroxyeicosanoic acid. The apparent Km value for 10-hydroxy-cis-12-octadecenoic acid (HYA) was estimated to be 38 μM with a kcat of 7.6 × 10-3 s-1. The apparent Km value for 10-oxo-cis-12-octadecenoic acid (KetoA) was estimated to be 1.8 μM with a kcat of 5.7 × 10-1 s-1. In the hydrogenation reaction of KetoA, both (R)- and (S)-HYA were generated, indicating that the enzyme has low stereoselectivity. This is the first report of a dehydrogenase with a preference for fatty acids with an internal hydroxy group.
Derivatization of Keto Fatty Acids: Part XI - Reaction of Ethanedithiol with α-Bromo, α,β-Unsaturated and β,γ-Unsaturated Ketones
Khan, Mushfiquddin,Siddiqui, M. S.,Osman, S. M.,Khan, Amjadullah
, p. 32 - 36 (2007/10/02)
Sulphur derivatives containing both the dithiolane and thioether moieties have been prepared by the reaction of ethanedithiol with α-bromoketone and α,β- and β,γ-unsaturated ketones.Reaction of ethanedithiol with 11-bromo-10-oxoundecanoic acid (I) gives the corresponding dithiolane containing thioether moiety at α-position as a major product (IV) alongwith a bromine containing noncyclised compound as a minor product (V).Methyl 4-oxo-trans-2-octadecenoate (II) reacts with the reagent and yields methyl 4-dithiolane-2(3)-thiolethylthiooctadecanoate (VI) alongwith methyl 4-dithiolane-trans-2-octadecenoate (VII) as minor product. 12-Oxo-cis-9-octadecenoic acid (III) is also found to react readily with ethanedithiol and affords 12-dithiolane-9(10)-thioacetoxyethylthiooctadecanoic acid (IX) and 12-dithiolane-9(10)-thiolethylthiooctadecanoic acid (X) as major and minor products, respectively.The spectral (IR, NMR, mass) data of the individual reaction products have been discussed.
