638-26-6Relevant articles and documents
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Pigulewski,Rubaschko
, (1940)
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Rational Engineering of Hydratase from Lactobacillus acidophilus Reveals Critical Residues Directing Substrate Specificity and Regioselectivity
Eser, Bekir Engin,Poborsky, Michal,Dai, Rongrong,Kishino, Shigenobu,Ljubic, Anita,Takeuchi, Michiki,Jacobsen, Charlotte,Ogawa, Jun,Kristensen, Peter,Guo, Zheng
, p. 550 - 563 (2019/11/25)
Enzymatic conversion of fatty acids (FAs) by fatty acid hydratases (FAHs) presents a green and efficient route for high-value hydroxy fatty acid (HFA) production. However, limited diversity was achieved among HFAs, to date, with respect to chain length and hydroxy position. In this study, two highly similar FAHs from Lactobacillus acidophilus were compared: FA-HY2 has a narrow substrate scope and strict regioselectivity, whereas FA-HY1 utilizes longer chain substrates and hydrates various double-bond positions. It is revealed that three active-site residues play a remarkable role in directing substrate specificity and regioselectivity of hydration. If these residues on FA-HY2 are mutated to the corresponding ones in FA-HY1, a significant expansion of substrate scope and a distinct enhancement in hydration of double bonds towards the ω-end of FAs is observed. A three-residue mutant of FA-HY2 (TM-FA-HY2) displayed an impressive reversal of regioselectivity towards linoleic acid, shifting the ratio of the HFA regioisomers (10-OH/13-OH) from 99:1 to 12:88. Notable changes in regioselectivity were also observed for arachidonic acid and for C18 polyunsaturated fatty acid substrates. In addition, TM-FA-HY2 converted eicosapentaenoic acid into its 12-hydroxy product with high conversion at the preparative scale. Furthermore, it is demonstrated that microalgae are a source of diverse FAs for HFA production. This study paves the way for tailor-made FAH design to enable the production of diverse HFAs for various applications from the polymer industry to medical fields.
METHOD FOR PRODUCING OPTICALLY ACTIVE HYDROXY FATTY ACID
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Paragraph 0117; 0126-0127, (2017/07/23)
PROBLEM TO BE SOLVED: To provide a means for producing optically active hydroxy fatty acid applicable to product materials having various structures, also having low production cost and high stereoselectivity. SOLUTION: Provided is a method for producing a compound represented by formula (I-1), including: a carbon chain connection step; the second oxidation step; a stereoselective reduction step; and the third oxidation step. Also provided is a method for producing a compound represented by formula (I-2), including: a carbon chain connection step; a speed theoretical optical resolution step; and the third oxidation step. SELECTED DRAWING: None COPYRIGHT: (C)2017,JPOandINPIT
Configurational Assignment of ‘Cryptochiral’ 10-Hydroxystearic Acid Through an Asymmetric Catalytic Synthesis
Brunner, Andreas,Hintermann, Lukas
, p. 928 - 943 (2016/12/09)
An asymmetric catalytic total synthesis of (S)-10-hydroxystearic acid (1) for comparison of its absolute configuration to that of samples obtained by fermentative hydration of oleic acid is reported. The synthesis involves two catalytic key-steps, namely Ru-catalyzed anti-Markovnikov hydration of 9-decynoic acid (7) to 10-oxodecanoic acid (5), followed by titanium-mediated asymmetric catalytic addition of dioctylzinc (25) to 5 in presence of the chiral ligand N,N’-((1R,2R)-cyclohexane-1,2-diyl)bis(1,1,1-trifluoromethanesulfonamide) (6). The synthesis is short and efficient and avoids use of protecting groups. Ozonolysis of 10-undecynoic acid (9) to 5 provides an alternative entry point into the synthetic route. The double dehydrobromination of (ω,ω-1)-dibromoalkanoic acids to ω-alkynoic acids under a variety of conditions was investigated with 10,11-dibromoundecanoic acid (11) as model substrate and using qNMR to quantify all reaction products. The synthetic approaches presented here have the potential to be generalized to the asymmetric catalytic synthesis of a variety of n-hydroxy-fatty acids.
