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
Biocatalytic study of novel oleate hydratases
Schmid, Jens,Steiner, Lisa,Fademrecht, Silvia,Pleiss, Jürgen,Otte, Konrad B.,Hauer, Bernhard
, p. S243 - S249 (2019/04/02)
The direct hydration of C[dbnd]C bonds to yield alcohols or the reverse dehydration is chemically challenging but highly sought after. Recently, oleate hydratases (OAHs) gained attention as biocatalytic alternatives capable of hydrating isolated, non-activated C[dbnd]C bonds. Their natural reaction is the conversion of oleic acid to (R)-10-hydroxystearic acid. In this work, we report the first comparative study of several OAHs. Therefore we established the Hydratase Engineering Database (HyED) comprising 2046 putative OAHs from eleven homologous families and selected nine homologs for cloning in E. coli. The heterologously expressed enzymes were evaluated concerning activity and substrate specificity. The enzymes have a broad substrate scope ranging from oleic acid (C18) to the novel synthetic substrate (Z)-undec-9-enoic acid (C11). The OAHs from Elizabethkingia meningoseptica and Chryseobacterium gleum showed the best expression, highest stability and broadest substrate scope, making them interesting candidates for directed evolution to engineer them for the application as general hydratase catalysts.