Applied Microbiology and Biotechnology

, Volume 76, Issue 1, pp 61–65 | Cite as

Microbial asymmetric oxidation of 2-butyl-1,3-propanediol

  • K. Mitsukura
  • T. Uno
  • T. Yoshida
  • T. Nagasawa
Biotechnological Products and Process Engineering


Microbial asymmetric oxidation of 2-butyl-1,3-propanediol was investigated for an efficient synthesis of S- and R-enantiomers of 2-hydroxymethylhexanoic acid (2-HMHA). From an intensive survey of the stocked bacterial strains, Acetobacter pasteurianus IAM 12073 and Pseudomonas putida IFO 3738 were found to show the highest S- and R-2-HMHA-producing activity, respectively. Under optimized conditions, A. pasteurianus (351 mg dry cell weight) and P. putida (642 mg dry cell weight) cells produced 12.0 g l−1 S-2-HMHA with 89% enantiomeric excess (e.e.) at 24 h of incubation and 5.1 g l−1 R-2-HMHA with 94% e.e. at 35 h of incubation from 2-butyl-1,3-propanediol.


Acetobacter pasteurianus Asymmetric oxidation 2-Butyl-1,3-propanediol 2-Hydroxymethylhexanoic acid Pseudomonas putida 


  1. Fujita M, Sakamoto M, Horiuchi N, Yamamoto T, Tomita K, Mizuno K, Niga T, Ito H, Kashimoto S (2004) Preparation of proline derivatives as antibacterial agents. PCT Int Appl WO-A1-2004018453Google Scholar
  2. Goodhue CT, Schaeffer JR (1971) Preparation of L(+)-β-hydroxyisobutyric acid by bacterial oxidation of isobutyric acid. Biotechnol Bioeng 13:203–214CrossRefGoogle Scholar
  3. Hasegawa J, Hamaguchi S, Ogura M, Watanabe K (1981a) Studies on β-hydroxylation acids II. Production of β-hydroxyisobutyric acids from aliphatic carboxylic acids by microorganisms. J Ferment Technol 59:257–262Google Scholar
  4. Hasegawa J, Ogura M, Hamaguchi S, Shimazaki M, Kawaharada H, Watanabe K (1981b) Studies on β-hydroxylation acids I. Stereoselective conversion of isobutyric acid to β-hydroxyisobutyric acid by microorganisms. J Ferment Technol 59:203–208Google Scholar
  5. Kapa PK, Jiang XL, Loeser EM, Slade J, Prashad M, Lee GT-S (2004) Process for preparing benzyloxyaminoacylpyrrolidinecarboxamides. PCT Int Appl WO-A1-2004026824Google Scholar
  6. Kawabata J, Ueda M (2005) Preparation of optically active carboxylic acid by stereoselective reduction. Jpn Kokai Tokyo Koho JP 2005318858Google Scholar
  7. León R, Prazeres DMF, Fernandes P, Molinari F, Cabral JMS (2001) A multiphasic hollow fiber reactor for the whole-cell bioconversion of 2-methyl-1,3-propanediol to (R)-β-hydroxyisobutyric acid. Biotechnol Prog 17:468–473CrossRefGoogle Scholar
  8. Miwa H, Hiyama C, Yamamoto M (1985) High-performance liquid chromatography of short-and long-chain fatty acids as 2-nitrophenylhydrazides. J Chromatogr A 321:165–174CrossRefGoogle Scholar
  9. Molinari F, Gondolfi R, Villa R, Urban E, Kiener A (2003) Enantioselective oxidation of prochiral 2-methyl-1,3-propanediol by Acetobacter pasteurianus. Tetrahedron: Asymmetry 14:2041–2043CrossRefGoogle Scholar
  10. Ohta H, Tetsukawa H, Noto N (1982) Enantiotopically selective oxidation of α,ω-diols with the enzyme systems of microorganisms. J Org Chem 47:2400–2404CrossRefGoogle Scholar
  11. Pfeffer PE, Kinsel E, Silbert LS (1972) α-Anions of carboxylic acids. V. Simple high yield preparation of α-alkylhydracrylic acid and α-alkylacrylic acids. J Org Chem 37:1256–1258CrossRefGoogle Scholar
  12. Taschner MJ, Black DJ, Chen Q-Z (1993) The enzymic Baeyer–Villiger oxidation: a study of 4-substituted cyclohexanones. Tetrahedron: Asymmetry 4:1387–1390CrossRefGoogle Scholar
  13. Tombo GMR, Schaer HP, Busquets XF, Ghisalba O (1986) Synthesis of both enantiomeric forms of 2-substituted 1,3-propanediol monoacetates starting from a common prochiral precursor, using enzymic transformations in aqueous and in organic media. Tetrahedron Lett 27:5707–5710CrossRefGoogle Scholar
  14. Toyama H, Fujii A, Matsushita K, Shinagawa, E, Ameyama M, Adachi O (1995) Three distinct quinoprotein alcohol dehydrogenases are expressed when Pseudomonas putida is grown on different alcohols. J Bacteriol 177:2442–2450Google Scholar

Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  1. 1.Department of Biomolecular Science, Faculty of EngineeringGifu UniversityGifuJapan

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