Microbial kinetic resolution of 2-substituted-1-propanol

Biocatalysis and Biotransformation

Volumn 27, Issue 1, 2009, Pages 66-70

  Miyamoto, K ^a   Fujimori, K ^a   Hirano, J I ^a   Ohta, H ^a  

^a KEIO UNIVERSITY   (Japan)

Author keywords

2 substituted 1 propanol; Enzymatic oxidation; Kinetic resolution; Screening

Indexed keywords

ACIDS; ETHANOL; OXIDATION; TERNARY SYSTEMS;

2-SUBSTITUTED-1-PROPANOL; CULTURAL CONDITIONS; ENANTIOSELECTIVELY; ENZYMATIC OXIDATION; KINETIC RESOLUTION; MICRO-ORGANISMS; PROPANOIC ACIDS; REACTION CONDITIONS;

PROPANOL;

HYDRATROPIC ACID; PHENETHYL ALCOHOL; PROPANOL; PROPIONIC ACID DERIVATIVE;

ARTHROBACTER; ARTICLE; BACTERIAL STRAIN; BACTERIUM CULTURE; BREVIBACTERIUM; CONTROLLED STUDY; ENANTIOMER; ENANTIOSELECTIVITY; MICROBIAL KINETICS; NONHUMAN; OXIDATION; PROCESS OPTIMIZATION; SOIL MICROFLORA;

EID: 58049194198     PISSN: 10242422     EISSN: 10292446     Source Type: Journal    
DOI: 10.1080/10242420802393352     Document Type: Article

References (17)

1. Basak, A., Nag, A., Bhattacharya, G., Mandal, S. and Nag, S. (2000) Chemoenzymatic synthesis of anti-inflammatory drugs in enantiomerically pure form. Tetrahed Asymm, 11, pp. 2403-2407.
2. Gandolfi, R., Ferrara, N. and Molinari, F. (2001) An easy and efficient method for the production of carboxylic acids and aldehydes by microbial oxidation of primary alcohols. Tetrahedron Lett, 42, pp. 513-514.
3. Honda, Y., Ori, A. and Tsuchihashi, G. (1987) A general synthetic method of chiral 2-arylalkanoic esters via thermal 1,2-rearrangement. Bull Chem Soc Jpn, 60, pp. 1027-1036.
4. Li, A., Yue, G., Li, Y., Pan, X. and Yang, T. (2003) Total asymmetric synthesis of (7S,9R)-(+)-bisacumol Tetrahed Asymm. 14, pp. 75-78.
5. Menicagli, R., Piccolo, O., Lardicci, L. and Wis, M. L. (1979) Optically active α- and β-naphthalene derivatives-β. Tetrahedron, 35, pp. 1301-1306.
6. Miyamoto, K., Hirano, J. and Ohta, H. (2004) Efficient oxidation of alcohols by a 2-phenylethanol-degrading Brevibacterium sp. Biotechnol Lett, 26, pp. 1386-1388.
7. Miyamoto, K. and Ohta, H. (1990) Enzyme-mediated asymmetric decarboxylation of disubstituted malonic acids. J Am Chem Soc, 112, pp. 4077-4078.
8. Miyamoto, K. and Ohta, H. (1992) Enantioselective oxidation of mandelic acid using a phenylmalonate metabolizing pathway of a soil bacterium Alcaligenes bronchispeticus KU 1201. Biotechnol Lett, 14, pp. 363-366.
9. Miyazawa, T., Kaito, A., Yukawa, T., Murashima, T. and Yamada, T. (2005) Enzymatic resolution of 2-aryloxy-1-propanols via lipase-catalyzed enantioselective acylation using acid anhydrides as acyl donors. J Mol Catal B Enzymatic, 37, pp. 63-67.
10. Morrone, R., Nicolosi, G., Patti, A. and Piattelli, M. (1995) Resolution of racemic flurbiprofen by lipase-mediated esterification in organic solvent. Tetrahed Asymm, 6, pp. 1773-1778.
11. Naemura, K., Murata, M., Tanaka, R., Yano, M., Hirose, K. and Tobe, Y. (1996) Enantioselective acylation of primary and secondary alcohols catalyzed by lipase QL from Alcaligenes sp.: A predictive active site model for lipase QL to identify which enantiomer of an alcohol reacts faster in this acylation. Tetrahed Asymm, 7, pp. 3285-3294.
12. Ohira, S., Kuboki, A., Hasegawa, T., Kikuchi, T., Kutsukake, T. and Nomura, M. (2002) Total synthesis of sporochnols, fish deterrents from a marine alga. Tetrahed Lett, 43, pp. 4641-4644.
13. Ohta, H. and Tetsukawa, H. (1979) Enantiotopically selective oxidation of 1, 3-diols with a microorganism. Chem Lett, 8, pp. 1379-1380.
14. Ohta, H. and Tetsukawa, H. (1981) Enantioselective oxidation of 1,5-diols with Gluconobacters preparation of (S)-mevalonolactone. Agric Biol Chem, 45, pp. 1895-1896.
15. Romano, A., Gandolfi, R., Rollini, M. and Molinari, F. (2002) Acetic acid bacteria as enantioselective biocatalysts. J Mol Catal B Enzymatic, 17, pp. 235-240.
16. Tsuchiya, S., Miyamoto, K. and Ohta, H. (1992) Highly efficient conversion of (+)-mandelic acid to its (R)-enantiomer by combination of enzyme-mediated oxidation and reduction. Biotechnol Lett, 14, pp. 1137-1142.
17. Wipf, P. and Ribe, S. (2000) Water/MAO acceleration of the zirconocene-catalyzed asymmetric methylalumination of α-olefins. Org Lett, 2, pp. 1713-1716.