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Title: Enantioselective benzylic hydroxylation of indan and tetralin with Pseudomonas monteilii TA-5
Authors: Lie, F. 
Chen, Y. 
Wang, Z. 
Li, Z. 
Issue Date: 5-Jun-2009
Citation: Lie, F., Chen, Y., Wang, Z., Li, Z. (2009-06-05). Enantioselective benzylic hydroxylation of indan and tetralin with Pseudomonas monteilii TA-5. Tetrahedron Asymmetry 20 (10) : 1206-1211. ScholarBank@NUS Repository.
Abstract: A set of 22 toluene- and ethylbenzene-degrading strains were screened for the enantioselective benzylic hydroxylation of indan and tetralin, and Pseudomonas monteilii TA-5 was discovered as an active and selective biocatalyst for such hydroxylations. Cells of P. monteilii TA-5 can be easily grown to a high density and demonstrated a specific hydroxylation activity of 24 U/g cdw (cell dry weight). Conditions for the hydroxylation of indan 1a and tetralin 1b with resting cells of this strain were optimized, to give the corresponding (R)-1-indanol 2a and (R)-1-tetralol 2b in 99% ee and 62-67% yields, respectively. No significant product inhibition was observed, and biohydroxylation with cell-free extracts suggested that the responsible hydroxylase is a soluble enzyme depending on either NADH or NADPH. Preparative biohydroxylation was demonstrated with resting cells as biocatalysts, affording (R)-2a in 99% ee and 65% yield, and (R)-2b in 99% ee and in 63% yield, respectively. © 2009 Elsevier Ltd. All rights reserved.
Source Title: Tetrahedron Asymmetry
ISSN: 09574166
DOI: 10.1016/j.tetasy.2009.04.006
Appears in Collections:Staff Publications

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