Abstract
Objectives
To investigate the efficiency of a new cascade biocatalysis system for the conversion of R, S-β-amino alcohols to enantiopure vicinal diol and β-amino alcohol.
Results
An efficient cascade biocatalysis was achieved by combination of a transaminase, a carbonyl reductase and a cofactor regeneration system. An ee value of > 99% for 2-amino-2-phenylethanol and 1-phenyl-1, 2-ethanediol were simultaneously obtained with 50% conversion from R, S-2-amino-2-phenylethanol. The generality of the cascade biocatalysis was further demonstrated with the whole-cell approaches to convert 10–60 mM R, S-β-amino alcohol to (R)- and (S)-diol and (R)- and (S)-β-amino alcohol in 90–99% ee with 50–52% conversion. Preparative biotransformation was demonstrated at a 50 ml scale with mixed recombinant cells to give both (R)- and (S)-2-amino-2-phenylethanol and (R)- and (S)-1-phenyl-1, 2-ethanediol in > 99% ee and 40–42% isolated yield from racemic 2-amino-2-phenylethanol.
Conclusions
This cascade biocatalysis system provides a new practical method for the simultaneous synthesis of optically pure vicinal diol and an β-amino alcohol.
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Acknowledgements
This study was financially supported by the National Natural Science Foundation of China (Grant No. 21772141), the Shanxi Province Science Foundation for Youths (Grant No. 201701D221042) and the Open Funding Project of the State Key Laboratory of Bioreactor Engineering.
Supporting information
Supplementary Table 1—Primers used for TAm cloning
Supplementary Fig. 1—The effect of 2-amino-2-phenylethanol on ωTAm activity
Supplementary Fig. 2—The effect of pyruvate on ωTAm activity
Supplementary Fig. 3—The effect of Ala on ωTAm activity
Supplementary Fig. 4—The effect of 2-hydroxyacetophenone on TAm activity
Supplementary Fig. 5—The effect of 2-amino-2-phenylethanol on ADH activity
Supplementary Fig. 6—Chiral GC analysis of 2-amino-2-phenylethanol (1a) standard
Supplementary Fig. 7—Chiral GC analysis of 2-amino-2-phenylethanol (1a) obtained via cascade biocatalysis with the resting cells of E. coli (TAm) and E. coli (CR–GDH)
Supplementary Fig. 8—Chiral GC analysis of 2-amino-1-butanol (1b)
Supplementary Fig. 9—Chiral GC analysis of 2-amino-1-butanol (1b) obtained via cascade biocatalysis with the resting cells of E. coli (TAm) and E. coli (CR–GDH)
Supplementary Fig. 10—Chiral GC analysis of 1-phenyl-1, 2-ethanediol (3a) standard
Supplementary Fig. 11—Chiral GC analysis of 1-phenyl-1, 2-ethanediol (3a) obtained via cascade biocatalysis with the resting cells of E. coli (TAm) and E. coli (CR–GDH)
Supplementary Fig. 12—Chiral GC analysis of 1, 2-butanediol (3b) standard
Supplementary Fig. 13—Chiral GC analysis of 1, 2-butanediol (3b) obtained via cascade biocatalysis with the resting cells of E. coli (TAm) and E. coli (CR–GDH)
Supplementary Fig. 14—Chiral GC analysis of 3b obtained via 2b asymmetric reduction with the resting cells of E. coli (GoSCR–GDH)
Supplementary Fig. 15—The purity analysis of 1a and 3a
Supplementary Fig. 16—1H NMR spectra analysis of chiral 2-amino-2-phenylethanol
Supplementary Fig. 17—1H NMR spectra analysis of chiral 1-phenyl-1, 2-ethanediol
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Zhao, JW., Wu, HL., Zhang, JD. et al. One pot simultaneous preparation of both enantiomer of β-amino alcohol and vicinal diol via cascade biocatalysis. Biotechnol Lett 40, 349–358 (2018). https://doi.org/10.1007/s10529-017-2471-6
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DOI: https://doi.org/10.1007/s10529-017-2471-6