Enantioselective Hydrolysis ofo-Nitrostyrene Oxide by Whole Cells ofAspergillus nigerCGMCC 0496

Enantioselective hydrolysis of various substituted styrene oxides with Aspergillus Niger CGMCC 0496Electronic supplementary information (ESI) available: experimental details. See http://www.rsc.org/suppdata/ob/b3/b312469j/

“…This confirmed our hypothesis. 9 After investigating the substitute site specificities of the strain, a range of substituted styrene oxides were investigated in order to broaden the applicability of this fungus (Scheme 3 and Table 5).…”

“…16 [α] 25 D ϩ32.2 (c 1.19, CHCl 3 ) for 99% ee, (S )}; MS m/z (rel. intensity %): 156, 154(M ϩ , 4, 16), 155, 153(M ϩ Ϫ 1, 10, 23), 134 (9), 124(28), 119(75), 91(33), 89(100), 63 (17); 1 H NMR (300 MHz, CDCl 3 , TMS): δ 2.65 (dd, 1H, J 1 = 5.9 Hz, J 2 = 3.6 Hz), 3.19 (dd, 1H, J 1 = 5.3 Hz, J 2 = 4.2 Hz), 4.21 (dd, 1H, J 1 = J 2 = 3.3 Hz), 7.10-7.50 (m, 4H); IR (film): ν max 3061, 2993, 1699, 1593, 1482, 1442, 1383, 1249, 1121, 1053, 1035, 880, 755 cm Ϫ1 . The enantiomeric excess was measured by capillary GC analysis using Chiraldex G-PN column (Astec).…”

“…Oil; >99% ee; [α] 18 D ϩ68.7 (c 1.1, CHCl 3 ); MS m/z (rel. intensity %): 200, 198(M ϩ , 17, 18), 199, 197(M ϩ Ϫ 1, 16,15), 185(1), 171 (9), 169 (10), 141(1), 120(7), 119(84), 91(63), 90(41), 89(100); 1 H NMR (300 MHz, CD 3 COCD 3 , TMS): δ 2.64 (dd, 1H, J 1 = 5.9 Hz, J 2 = 2.6 Hz), 3.18 (dd, 1H, J 1 = 5.9 Hz, J 2 = 4.1 Hz), 4.15 (dd, 1H, J 1 = 4.1 Hz, J 2 = 2.6 Hz), 7.08-7.38 (m, 3H), 7.54 (dd, 1H, J 1 = 7.9 Hz, J 2 = 1.1 Hz); IR (film): ν max 3055, 2991, 2916, 1569, 1472, 1440, 1381, 1248, 1045, 1026, 879, 753 cm Ϫ1 . The enantiomeric excess was measured by capillary GC analysis using Chiraldex G-PN column (Astec).…”

“…A lot of microbial origin EHs have been identified, 7 and some show extremely good enantioselectivity when hydrolyzing para-substituted styrene oxides. 8 However, there have been few results on the substrates of ortho- 9 and meta-substituted styrene oxides. More recently, we screened EHs among several strains of Aspergillus niger which were isolated from soil.…”

“…Several of them were found to have extremely highly active and enantioselective EHs, 10 especially A. niger CGMCC 0496. 9 In this paper, we investigated the biocatalytic hydrolysis of various substituted styrene oxides using whole cells of A. niger CGMCC 0496.…”