Deracemization of (±)-cis-2,3-epoxyheptane via enantioconvergent biocatalytic hydrolysis using Nocardia EH1-epoxide hydrolase

Tetrahedron Letters

Volumn 37, Issue 46, 1996, Pages 8379-8382

  Kroutil, Wolfgang ^a   Mischitz, Martin ^a   Plachota, Peter ^a   Faber, Kurt ^a  

^a GRAZ UNIVERSITY OF TECHNOLOGY   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL ENZYME; EPOXIDE HYDROLASE; RACEMASE;

ARTICLE; HYDROLYSIS; NOCARDIA; RACEMIC MIXTURE;

BACTERIA (MICROORGANISMS); NOCARDIA;

EID: 0030580210     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01935-1     Document Type: Article

References (13)

1. 1. Faber, K.; Mischitz, M and Kroutil, W. Acta Chem. Scand. 1996, 50, 249.
2. 2. Pedragosa-Moreau, S.; Archelas, A. and Furstoss, R. Bull. Soc. Chim. Fr. 1995, 132, 769.
3. 3. Bellucci, G.; Berti, G.; Catelani, G. and Mastroriili, E. J. Org, Chem. 1981, 46, 5148.
4. 4. Bellucci, G.; Chiappe, C. and Cordoni, A. Tetrahedron: Asymmetry 1996, 7, 197.
5. 5. Blée, E. and Schuber, F. Eur. J. Biochem. 1995, 230, 229.
6. 6. Pedragosa-Moreau, S.; Archelas, A. and Furstoss, R. Tetrahedron 1996, 52, 4593.
7. 7. The e.e.-time data of Scheme 1 were obtained from an analytical-scale experiment. No trace of spontaneous hydrolysis was observed in the absence of biocatalyst within 600 h.
8. 20 +20.45°, c=1, EtOH).
9. 9. Obtained by hydrophobic interaction chromatography on Phenyl Sepharose CL-4B. Preliminary data indicate that the epoxide hydrolase from Nocardia EH1 is related to the enzyme from Rhodococcus sp. NCIMB 11216, i. e. a constitutive, soluble enzyme having a MW of ∼35 kDa. See: Mischitz, M.; Faber, K. and Willetts, A. Biotechnol. Lett. 1995, 17, 893. Full details of the purification and characterization of the enzyme will be published in a separate paper.
10. ret: (2S,3S)-diol 3.9min, (2R,3R)-diol 4.13min. Quadrupol-MS: EI 70eV, 130°C, auxiliary temp. 180°C.
11. 11. For experimental details see: Mischitz, M.; Mirtl, C.; Saf, R. and Faber, K. Tetrahedron: Asymmetry 1996, 7, 2041.
12. 12. A full treatment of the mathematical model describing enantioconvergent processes will be published in a full paper.
13. 2O) to furnish (2S,3S)-and (2S,3R)-heptane-2,3-diol.