Sporobolomyces salmonicolor

Many aldehyde reductases transform both aldehydes and ketones. For example, phenylacetaldehyde reductase (PAR) from a styrene-assimilating Corynebacterium strain, ST-10, reduces hexyl aldehyde and phenylacetaldehyde [22aj. Other aldehyde reductases such as one from Sporobolomyces salmonicolor also reduce aldehydes as well as ketones [22b]. 

Two interesting yeast carbonyl reductases, one from Candida magnoliae (CMCR) [33,54] and the other from Sporobolomyces salmonicolor (SSCR) [55], were found to catalyze the reduction of ethyl 4-chloro-3-oxobutanoate to give ethyl (5)-4-chloro-3-hydroxybutanoate, a useful chiral building block. In an effort to search for carbonyl reductases with anti-Prelog enantioselectivity, the activity and enantioselectivity of CMCR and SSCR have been evaluated toward the reduction of various ketones, including a- and /3-ketoesters, and their application potential in the synthesis of pharmaceutically important chiral alcohol intermediates have been explored [56-58]. 

Figure 7.18 Reduction of a-ketoesters by a carbonyl reductase from Sporobolomyces salmonicolor (SSCR)...

Kita, K., Nakase, K.-i., Yanase, H. et al. (1999) Purification and characterization of new aldehyde reductases from Sporobolomyces salmonicolor AKU4429. Journal of Molecular Catalysis B-Enzymatic, 6 (3), 305-313. 

Zhu, D., Yang, Y., Buynak, J.D. and Hua, L. (2006) Stereoselective ketone reduction by a carbonyl reductase from Sporobolomyces salmonicolor. Substrate specificity, enantioselectivity and enzyme—substrate docking studies. Organic and Biomolecular Chemistry, 4 (14), 2690-2695. 

The reduction of 4-chloroacetoacetate ethyl ester (CAAE) to 4-chloro-3-hydroxy-butanoate ethyl ester (CHBE) usually proceeds stereospecifically [54, 55]. This activity is widely distributed in yeasts, molds and bacteria, most of which give the (S)-enantiomer. Sporobolomyces salmonicolor was found to produce the (l )-enan-tiomer predominantly (62% e. e.) with high molar conversion [54,55], and several Candida yeasts formed (S)-CHBE of high optical purity (> 90% e. e.) [54,55]. 

Kataoka, M., Sakai, H., Morikawa, T., Katoh, M., Miyoshi, T., Shimizu, S., and Yamada, H. 1992b. Characterization of aldehyde reductase of Sporobolomyces salmonicolor. Biochim. Biophys. Acta, 1122, 57-62. 

Kita, K., Matsuzaki, K., Hashimoto, T., Yanase, H., Kato, N., Chung, M. C.-M., Kataoka, M., and Shimizu, S. 1996. Cloning of the aldehyde reductase gene from a red yeast, Sporobolomyces salmonicolor, and characterization of the gene and its product. Appl. Environ. Microbiol., 62, 2303-2310. 

Synthetic statins are important lipid regulating drugs for the treatment of atherosclerosis and other diseases related to hyperlipidaemia, especially coronary heart disease. As the pharmacophore, all synthetic statins contain a saturated or partially unsaturated syn-3,5-dihydroxy C7-carboxylate. An important building block for the synthesis of the side chain is represented by 4-chloro-3-hydroxybutanoate esters (CHBE). Both enantiomers can be obtained by enzyme-catalyzed reduction of the (1-keto ester. The group of Kataoka and Shimizu found that an aldehyde reductase of Sporobolomyces salmonicolor [161] and a carbonyl reductase of Candida... 

Fig. 42 Stereospecific reduction of 4-chloro-3-oxobutanoate ester (COBE) to (K) and (S)-4-chloro-3-hydroxybutanoate ester (CHBE) by aldehyde reductase from Sporobolomyces salmonicolor and carbonyl reductase from Candida magnoliae, respectively...

Besides these examples, many other important enzymes for biocatalytic reductions, such as the NADPH-dependent carbonyl reductase from Candida magnoliae U2 the ketoreductase from Zygosaccharomyces rowxii11431, and the aldehyde reductase from Sporobolomyces salmonicolor AKU442911441, etc. have also been expressed in E. coli etc. and shown to be active. 

Ethyl (7 )-4-chloro-3-hydroxyb utanoate Aldehyde reductase (from Sporobolomyces salmonicolor, overexpressed in E. Coli) 300 (100)... 

Li, H., Zhu, D., Hua, L., and Biehl, E.R. (2009) Enantioselective reduction of diaryl ketones catalyzed by a carbonyl reductase from Sporobolomyces salmonicolor and its mutant enzymes. Adv. Synth. Catal., 351, 583-588. 

---