Biotechnology Letters

, Volume 40, Issue 2, pp 349–358 | Cite as

One pot simultaneous preparation of both enantiomer of β-amino alcohol and vicinal diol via cascade biocatalysis

  • Jian-Wei Zhao
  • Hua-Lei Wu
  • Jian-Dong Zhang
  • Wen-Chao Gao
  • Xiao-Jun Fan
  • Hong-Hong Chang
  • Wen-Long Wei
  • Jian-He Xu
Original Research Paper
  • 90 Downloads

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.

Keywords

β-Amino alcohol Carbonyl reductase Cascade biocatalysis Transaminase Vicinal diol 

Notes

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

Supplementary material

10529_2017_2471_MOESM1_ESM.doc (4.5 mb)
Supplementary material 1 (DOC 4606 kb)

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Copyright information

© Springer Science+Business Media B.V., part of Springer Nature 2017

Authors and Affiliations

  • Jian-Wei Zhao
    • 1
  • Hua-Lei Wu
    • 1
  • Jian-Dong Zhang
    • 1
  • Wen-Chao Gao
    • 1
  • Xiao-Jun Fan
    • 1
  • Hong-Hong Chang
    • 1
  • Wen-Long Wei
    • 1
  • Jian-He Xu
    • 2
  1. 1.Department of Biological and Pharmaceutical Engineering, College of Chemistry and Chemical EngineeringTaiyuan University of TechnologyTaiyuanPeople’s Republic of China
  2. 2.Laboratory of Biocatalysis and Bioprocessing, State Key Laboratory of Bioreactor EngineeringEast China University of Science and TechnologyShanghaiPeople’s Republic of China

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