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Int. J. Mol. Sci. 2012, 13(10), 13542-13553; doi:10.3390/ijms131013542
Article

Production of (R)-3-Quinuclidinol by E. coli Biocatalysts Possessing NADH-Dependent 3-Quinuclidinone Reductase (QNR or bacC) from Microbacterium luteolum and Leifsonia Alcohol Dehydrogenase (LSADH)

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Received: 30 August 2012; in revised form: 27 September 2012 / Accepted: 11 October 2012 / Published: 19 October 2012
(This article belongs to the Special Issue Organic Synthesis Using Biocatalyst)
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Abstract: We found two NADH-dependent reductases (QNR and bacC) in Microbacterium luteolum JCM 9174 (M. luteolum JCM 9174) that can reduce 3-quinuclidinone to optically pure (R)-(−)-3-quinuclidinol. Alcohol dehydrogenase from Leifsonia sp. (LSADH) was combined with these reductases to regenerate NAD+ to NADH in situ in the presence of 2-propanol as a hydrogen donor. The reductase and LSADH genes were efficiently expressed in E. coli cells. A number of constructed E. coli biocatalysts (intact or immobilized) were applied to the resting cell reaction and optimized. Under the optimized conditions, (R)-(−)-3-quinuclidinol was synthesized from 3-quinuclidinone (15% w/v, 939 mM) giving a conversion yield of 100% for immobilized QNR. The optical purity of the (R)-(−)-3-quinuclidinol produced by the enzymatic reactions was >99.9%. Thus, E. coli biocatalysis should be useful for the practical production of the pharmaceutically important intermediate, (R)-(−)-3-quinuclidinol.
Keywords: 3-quinuclidinone reductase (QNR and bacC); Microbacterium luteolum JCM 9174; Leifsonia alcohol dehydrogenase (LSADH); (R)-(−)-3-quinuclidinol; optically pure alcohol; immobilized biocatalyst 3-quinuclidinone reductase (QNR and bacC); Microbacterium luteolum JCM 9174; Leifsonia alcohol dehydrogenase (LSADH); (R)-(−)-3-quinuclidinol; optically pure alcohol; immobilized biocatalyst
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Isotani, K.; Kurokawa, J.; Itoh, N. Production of (R)-3-Quinuclidinol by E. coli Biocatalysts Possessing NADH-Dependent 3-Quinuclidinone Reductase (QNR or bacC) from Microbacterium luteolum and Leifsonia Alcohol Dehydrogenase (LSADH). Int. J. Mol. Sci. 2012, 13, 13542-13553.

AMA Style

Isotani K, Kurokawa J, Itoh N. Production of (R)-3-Quinuclidinol by E. coli Biocatalysts Possessing NADH-Dependent 3-Quinuclidinone Reductase (QNR or bacC) from Microbacterium luteolum and Leifsonia Alcohol Dehydrogenase (LSADH). International Journal of Molecular Sciences. 2012; 13(10):13542-13553.

Chicago/Turabian Style

Isotani, Kentaro; Kurokawa, Junji; Itoh, Nobuya. 2012. "Production of (R)-3-Quinuclidinol by E. coli Biocatalysts Possessing NADH-Dependent 3-Quinuclidinone Reductase (QNR or bacC) from Microbacterium luteolum and Leifsonia Alcohol Dehydrogenase (LSADH)." Int. J. Mol. Sci. 13, no. 10: 13542-13553.



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