Biocatalysis of nitro substituted styrene oxides by non-conventional yeasts.
Yeast strains (410) from more than 45 different genera were screened for the enantioselective hydrolysis of nitro substituted styrene oxides. These strains included 262 yeasts with known epoxides hydrolase activity for various other epoxides. Epoxide hydrolase activity for p-nitrostyrene oxide (pNSO) (177 strains) and m-nitrostyrene oxide (mNSO) (148 strains) was widespread in the yeasts, while activity for o-nitrostyrene oxide (oNSO) was less ubiquitous (22 strains). The strains that displayed enantioselectivity in the hydrolysis of one or more of the nitro substituted styrene oxides (35 strains) were also screened against styrene oxide (SO). Rhodosporidium toruloides UOFS Y-0471 displayed the highest enantioselectivity for pNSO (ee 55%, yield 35%) while Rhodotorula glutinis UOFS Y-0653 displayed the highest enantioselectivity for mNSO (ee > 98%, yield 29%), oNSO (ee 39%, yield 19%) and SO (ee > 98%, yield 19%). (R)-Styrene oxide was preferentially hydrolysed to the corresponding (R)-diol with retention of configuration at the stereogenic centre. In the case of the nitro substituted styrene oxides the absolute configurations of the remaining epoxides and the formed diols were not established.
Yeates
C A
CA
Department of Pharmaceutical Chemistry, Potchefstroom University for Christian Higher Education, Private Bag X6001, Potchefstroom 2520, South Africa. fchcay@puknet.puk.ac.za
van Dyk
M S
MS
Botes
A L
AL
Breytenbach
J C
JC
Krieg
H M
HM
D002384:Catalysis; D002478:Cells, Cultured; D004851:Epoxide Hydrolases / Q000737:chemistry / Q000145:classification* / Q000378:metabolism*; D004852:Epoxy Compounds / Q000737:chemistry / Q000145:classification / Q000378:metabolism*; D013045:Species Specificity; D013237:Stereoisomerism; D015003:Yeasts / Q000737:chemistry / Q000145:classification* / Q000201:enzymology*
D004852:Epoxy Compounds; C033332:4-nitrostyrene oxide; C013690:styrene oxide; D004851:Epoxide Hydrolases