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Biotechnology Letters

, Volume 34, Issue 9, pp 1741–1744 | Cite as

Regioselective synthesis of 1,3,5-adamantanetriol from 1,3-adamantanediol using Kitasatospora cells

  • Koichi Mitsukura
  • Naoki Yamanaka
  • Toyokazu Yoshida
  • Toru Nagasawa
Original Research Paper

Abstract

Washed cells (62 mg) of Kitasatospora sp. GF12 in 4 ml buffer (pH 7) catalyzed the regioselective hydroxylation of 60 mM 1,3-adamantanediol [1,3-ad(OH)2] to 30.9 mM 1,3,5-adamantanetriol [1,3,5-ad(OH)3] over 120 h at 24 °C. Glycerol at 400 mM was added to the reaction mixture to recycle the intracellular NADH/NADPH. Whole cells of GF12, also catalyzed the hydroxylation of 10 mM 1-adamantanol (1-adOH), to 3.6 mM 1,3,5-ad(OH)3.

Keywords

1,3-Adamantanediol 1,3,5-Adamantanetriol Hydroxylation Kitasatospora sp. Regioselectivity 

Notes

Acknowledgments

This study was supported in part by the project for Development of Basic Technologies for Advanced Production Methods using Microorganism Functions in the New Energy and Industrial Technology Development Organization (NEDO) of Japan. We are grateful to the Life Science Research Center of Gifu University for NMR and mass spectroscopy.

Supplementary material

10529_2012_960_MOESM1_ESM.doc (3.6 mb)
Supplementary material 1 (DOC 3683 kb)

References

  1. Ahrén B, Landin-Olsson M, Ridyard CH, Jansson PA, Svensson M, Holmes D, Schweizer A (2004) Inhibition of dipeptidyl peptidase-4 reduces glycemia, sustains insulin levels, and reduces glucagons levels in type 2 diabetes. J Clin Endocrinol Metab 89:2078–2084PubMedCrossRefGoogle Scholar
  2. Bailey PD, Higgins SD, Ridyard CH, Roberts SM, Rosair GM, Whittaker RA, Willetts AJ (1996) Selective hydroxylation of 1-substituted adamantanes using Absidia cylindrospora (I.M.I 342950). Chem. Commun 1833–1834Google Scholar
  3. Mitsukura K, Kondo Y, Yoshida T, Nagasawa T (2006) Regioselective hydroxylation of adamantane by Streptomyces griseoplanus cells. Appl Microbiol Biotechnol 71:502–504PubMedCrossRefGoogle Scholar
  4. Mitsukura K, Sakamoto H, Kubo H, Yoshida T, Nagasawa T (2010) Bioconversion of 1-adamantanol to 1,3-adamantanediol using Streptomyces sp. SA8 oxidation system. J Biosci Bioeng 109:550–553PubMedCrossRefGoogle Scholar
  5. Sanders DP (2010) Advances in patterning materials for 193 nm immersion lithography. Chem Rev 110:321–360PubMedCrossRefGoogle Scholar
  6. Shirling EB, Gottlieb D (1966) Method for classification of Streptomyces species. Int J Syst Bacteriol 16:313–340CrossRefGoogle Scholar
  7. Urlacher VD, Girhard M (2011) Cytochrome P450 monooxygenases: an update on perspectives for synthetic application. Trends Biotechnol 30:26–36PubMedCrossRefGoogle Scholar
  8. White RE, McCarthy M-B, Egeberg KD, Sligar SG (1984) Regioselectivity in the cytochromes P-450: control by protein constraints and by chemical reactivities. Arch Biochem Biophys 228:493–502PubMedCrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media B.V. 2012

Authors and Affiliations

  • Koichi Mitsukura
    • 1
  • Naoki Yamanaka
    • 1
  • Toyokazu Yoshida
    • 1
  • Toru Nagasawa
    • 1
  1. 1.Department of Biomolecular ScienceGifu UniversityGifuJapan

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