Summary
Pseudomonas sp. OS-K-29 assimilated (R)-2,3-dichloro-1-propanol preferentially as the sole source of carbon. Isolation of optically pure (S)-2,3-dichloro-1-propanol with 100% enantiomer excess (e.e.) from the racemate was done based on this bacterial assimilation using immobilized-cells of OS-K-29 with calcium-alginate. The overall examination of the reactor involved 19 batches for 50 days without loss of its activity. Highly pure (R)-epichlorohydrin with 99.5% e.e. was prepared from the (S)-2,3-dichloro-1-propanol with treatment of aqueous NaOH. This new method is simple and useful for manufacturing optically active (S)-2,3-dichloro-1-propanol and (R)-epichlorohydrin.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
McClure, D.E., E.L. Engelhaldt, K. Mensler, S. King, W.S. Saari, J.R. Huff and J.J. Baldwin. 1979. Chiral heteroaryloxymethyloxiranes. J. Org. Chem. 44: 1826–1831.
Cimetiere, B., L. Jacob and M. Julia. 1986. Resolution of oxiranes. Application to the synthesis of the platelet aggregation factor. Tetrahedron Lett. 27: 6329.
Takano, S., M. Yanase, Y. Sekiguchi and K. Ogasawara. 1987. Practical synthesis of (R)-γ-amino-β-hydroxybutanoic acid (GABOB) from (R)-epichlorohydrin. Tetrahedron Lett. 28: 1783–1784.
Koden, M., T. Kuratate, F. Funada, K. Awane, K. Sakaguchi, Y. Shiomi and K. Kitamura. 1989. Ferroelectric liquid crystals incorporating the optically active γ-lactone ring. Jpn. J. Applied Physics. 29: 981–983.
Baldwin, J.J., A.W. Raab, K. Mensler, B.H. Arson and D.E. McClure. 1978. Synthesis of (R)- and (S)-epichlorohydrin. J. Org. Chem. 42: 4876–4878.
Ellis, M.K., B.T. Golding and P. Watson. 1984. Kinetic resolution of 1,2-diol withd-camphorquinone, preparation of (R)-(chloromethyl)oxirane. J. Chem. Soc., Chem. Commun., 1600–1602.
Russel, S.W., H.J.J. Pabon. 1982. Synthesis of (R,S)-(5Z, 8E, 10E)-12-hydroxyheptadeca-5, 8, 10-trienoic acid and (R, S) and (S)-(5Z, 8Z, 10E, 14Z)-12-hydroxyeicosa-5, 8, 10, 14-tetraenoic acid and their racemic 5, 6, 8, 9-tetradeuterio isomers. J. Chem. Soc. Perkin I, 546: 545–552.
Iriuchijima, S., A. Keiyu and N. Kojima. 1982. Asymmetric hydrolysis of (±)-1-acetoxy-2,3-dichloropropane with enzymes and microorganisms. Agric. Biol. Chem. 46: 1593–1597.
Cambou B. and A.M. Klibanov. 1982. Preparative production of optically active esters and alcohols using esterase-catalyzed stereospecific transesterification in organic media. J. Am. Chem. Soc. 106: 2687–2692.
Kasai, N., K. Tsujimura, K. Unoura and T. Suzuki. 1990. Degradation of 2,3-dichloro-1-propanol byPseudomonas sp. Agric. Biol. Chem. 54: 3185–3190.
Dale, J.A., D.L. Dull and H.S. Mosher. 1969. α-Methoxytrifluoromethylphenyl acetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and amines. J. Org. Chem. 34: 2543–2549.
Schurig, V. 1988. Enantiomer analysis by complexation chromatography. J. Chromatography. 441: 135–153.
Maeda, H., S. Yamazaki, K. Oobuchi and S. Kajiwara. 1988. Bioreactor for Assymetric Synthesis, edited by Gakkai Syuppan Center, Tokyo.
Bryan Jones, J., 1986. Enzymes in organic synthesis. Tetrahedron. 42: 3351–3403.
Takano, S., M. Yanase, M. Takahashi and K. Ogasawara. 1987. Enantiodivergent synthesis of both enantiomers of Sulcatol and Matsutake alcohol from (R)-epichlorohydrin. Chem. Lett. 2017–2020.
Imai T. and S. Nishida. 1990. Lewis acid promoted ring-opening allylation of epichlorohydrin with allylic silanes and stannanes to afford 1-chloro-5-alken-2-ols. A short synthesis of (S)-(-)-Ipsenol. J. Org. Chem. 55: 4849–4853.
Kawamura, K., T. Ohta and G. Otani. 1990. An efficient synthesis of the optical isomers of nipradiol. Chem. Pharm. Bull. 38: 2092–2096.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Kasai, N., Tsujimura, K., Unoura, K. et al. Preparation of (S)-2,3-dichloro-1-propanol byPseudomonas sp. and its use in the synthesis of (R)-epichlorohydrin. Journal of Industrial Microbiology 9, 97–101 (1992). https://doi.org/10.1007/BF01569739
Received:
Revised:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/BF01569739