12-Hydroxystearic acid

Yang, W., L. Dostal, and J. P. N. Rosazza, Stereospecificity of microbial hydrations of oleic acid to 10-hydroxystearic acid , Appl. Environ. Microbiol., 59, 281-284 (1993). 

It has been reported that a microbial isolate, Flavobacterium sp. strain DS5, produced 10-ketostearic acid (10-KSA) from oleic acid in 85% yield (Hou, 1994a). The purified product was white, plate-like crystals melting at 79.2°C. A small amount of 10-hydroxystearic acid (10-HSA) was also produced during the bioconversion, suggesting that oleic acid is converted to 10-KSA via 10-HSA, and the enzyme catalyzing the hydration is C-10 positional specific (Hou, 1994b, 1995). The DS5 bioconversion products from oleic, linoleic, a-linolenic, and y-linolenic acid are all 10-hydroxy fatty acids. The optimum time, pH, and temperature for the production of 10-KSA have been reported in flask... 

Since Wallen et al. (1962) reported the first bioconversion of oleic acid to 10-hydroxystearic acid by a Pseudomonad, microbial conversions of unsaturated fatty acids from different substrates by various microbial strains have been widely exploited to produce new, value-added products. Among the unsaturated fatty acids used for microbial production of hydroxy fatty acids, three (oleic, linoleic, and linolenic acids) were well studied as substrates to produce mono-, di-, and trihydroxy fatty acids. Recently, a bacterial strain Pseudomonas aeruginosa NRRL B-18602 (PR3) has been studied to produce hydroxy fatty acids from several fatty acid substrates. In this review, we introduce the production of hydroxy fatty acids from their corresponding fatty acid substrates by P. aeruginosa PR3 and their industrially valuable biological activities. 

Wallen, L. L., Benedict, R. G., and Jackson, R. W. 1962. The microbiological production of 10-hydroxystearic acid from oleic acid. Arch. Biochem. Biophys., 99,249-253. 

Monohydroxy Fatty Acid Production of 10-Hydroxystearic Acid... 

Hydroxystearic acid High melting point, thermostable, gel state at room temperature and non-toxie Lubricant Kim and Oh, 2013... 

Joo, YC Seo, ES Kim, YS Kim, KR Park, JB Oh, DK. Production of 10-hydroxystearic acid from oleic acid by whole eells of recombinant Escherichia coli containing oleatehydratase from Stenotropho-monasmaltophilia. Journal of Biotechnology, 2012, v. 158, 17-23. 

The enzymes involved in this reaction and the structure of the intermediate are not known. Because 9-hydroxystearic acid or 10-hydroxystearic acid can replace oleate for the growth of yeast, it was proposed that hydroxystearic acid is an intermediate in the formation of oleate. It is now clear that this is true. 

Fig. 13 This schematic is a depiction of the two models that are associated with ion permeation through lipid membranes containing some HSA (10-hydroxystearic acid) (smaller headgroup and one hydroxylated acyl chain). The lipids are represented by larger headgroups and two acyl chains, and are shown to form two zones that are rich in lipid, and which differ in density (phase domains). Conductivity through zone A is by electrostatic stabilization of ions occur by hydroxyl moieties that exist in domains that are rich in HSA. Conductivity in zone B also involves stabilization of charge by hydroxyl moieties, but it also shows the steric disorder that can exist between domains. This figure is published with permission (Nikolelis et al. 1991)...

A procedure starting from oleic acid and involving two biocatalysts was reported in the 1990s [136,137]. A gram-positive strain of bacteria catalyzed the enantioselective hydration of oleic acid into (10/ )-hydroxystearic acid, which was subsequently converted by baker s yeast into (4/ )-hydroxydodecanoic acid via three -oxidation cycles. After cyclization, (fJ)-y-dodecalactone was obtained in over 22% yield with respect to the initial substrate (Scheme 9.5). 

Many studies have focused on 10-hydroxystearic acid production from oleic acid, but production via recombinant cells has been attempted only recently [138]. A putative fatty acid hydratase from Stenotrophomonas maltophilia was cloned and expressed in E. coli. The recombinant enzyme showed the highest hydration activity for oleic acid among the fatty acids tested, indicating that the enzyme is an oleate hydratase. The optimal conditions for the production of 10-hydroxystearic acid were pH 6.5, 35 °C, 0.05% w/v Tween 40,10 gl cells, and 50gl oleic acid. Under these conditions, whole recombinant cells produced 49gl 10-hydroxystearic acid for 4h, with a conversion yield of 98%w/w and a volumetric productivity of 12.3 gl h , which were 18% and 2.5-fold higher than those of whole wild-type S. maltophilia cells, respectively. 

The use of the permeabilized Waltomyces lipofer allowed y-dodecalactone to be prepared [139] with the highest concentration, conversion yield, and productivity so far reported. At pH 6.5,35 °C, 200 rpm, 0.7 M Tris, 60 gl of 10-hydroxystearic acid, and 30 gU of cells, the lactone was obtained after 30 h with a conversion yield of 76%w/w and a productivity of 1.5 gl h . These values were 3.7- and 3.8-fold higher than those obtained using non-permeabilized cells. 

Kim BN, Joo YC, Kim YS, Kim KR, Oh DK (2012) Production of 10-hydroxystearic acid fi om oleic acid and olive oil hydrolyzate by an oleate hydratase fi om Lysinibacillus fiisiformis. Appl Microbiol Biotechnol 95(4) 929-937. doi 10.1007/s00253-011-3805-2 Kongo JM (ed) (2013) Lactic acid bacteria—R D for food, health and livestock purposes, InTech, Rijeka, Croatia, doi 10.5772/2825 ISBN 978-953-51-0955-6 Klimin B, Mlinch T (1998) Microbiological process for producing gamma-decalactone. US patent No 5 849551A... 

Kuo TM, Levinson WE (2006) Biocatalytic production of 10-hydroxystearic acid, 10-ketosteaiic acid, and their primary fatty amides. Agriculture 83(8) 671-675 Kuo TM, Lanser AC, Nakamura LK, Hou CT (2000) Production of 10-ketostearic acid and 10-hydroxystearic acid by strains of Sphingobacterium thalpophilum isolated fi om composted manure. Curr Microbiol 40 105-109. doi 10.1007/s002849910020... 

Many biochemical reductions occur at sp -hybridized carbon atoms. These reactions yield a single enantiomer. For example, the hydration of oleic acid yields exclusively (i )-10-hydroxystearic acid. 

Lennarz and Bloch (1960) have prepared 9-hydroxystearic acid-H from naturally occurring J -9-hydroxyoctadecenoic acid by catalytic hydrogenation, and racemic 10-hydroxystearic acid through epoxidation of oleic acid, and tested them as possible precursors to olefinic acids in two ways. Both were as efficient as oleic acid in satisfying the unsaturated fatty acid growth requirement of yeast raised under strictly anaerobic conditions, suggesting that they were desaturated to olefinic acids in vivo. 9-Hydroxystearic acid-H in addition was incubated with yeast homogenate in the presence of TPNH, ATP, and CoA, and yielded a monounsaturated acid with a double bond in the vicinity of C-8 to C-10. 

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