Skip to main content
Log in

Enzymatic Synthesis of Aliphatic Primary ω-Amino Alcohols from ω-Amino Fatty Acids by Carboxylic Acid Reductase

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

Medium to long chain aliphatic amino alcohols have numerous applications in polymer-based industries. We herein report a biocatalytic reduction of amino fatty acids into corresponding amino alcohols using carboxylic acid reductase and E coli endogenous aldehyde reductases. Interestingly, employing this reaction in tandem with minimizing the hurdle of substrate insolubility, the biocatalysts successfully produced 5.76 mM 12-amino-1-dodecanol from 10 mM of corresponding 12-amino-dodecanoic acid. Finally, up to 9.17 mM of 8-amino-1-octanol was obtained in 24 h on a preparative scale reaction of 50 mM substrate.

Graphic Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Bozell JJ, Petersen GR (2010) Green Chem 12:539

    Article  CAS  Google Scholar 

  2. Reetz MT (2013) J Am Chem Soc 135:12480

    Article  CAS  Google Scholar 

  3. Lee JW, Kim HU, Choi S, Yi J, Lee SY (2011) Curr Opin Biotechnol 22:758

    Article  CAS  Google Scholar 

  4. Biermann U, Bornscheuer U, Meier MA, Metzger JO, Schafer HJ (2011) Angew Chem Int Ed 50:3854

    Article  CAS  Google Scholar 

  5. Patil MD, Grogan G, Bommarius A, Yun H (2018) ACS Catal 8:10985

    Article  CAS  Google Scholar 

  6. Patil MD, Grogan G, Bommarius A, Yun H (2018) Catalysts 8:254

    Article  Google Scholar 

  7. Sattler JH, Fuchs M, Mutti FG, Grischek B, Engel P, Pfeffer J, Woodley JM, Kroutil W (2014) Angew Chem Int Ed 53:14153

    Article  CAS  Google Scholar 

  8. Seo JH, Lee SM, Lee J, Park JB (2015) J Biotechnol 216:158

    Article  CAS  Google Scholar 

  9. Ahsan MM, Sung S, Jeon H, Patil MD, Chung T, Yun H (2018) Catalysts 8:4

    Article  Google Scholar 

  10. Ahsan MM, Jeon H, Nadarajan S, Chung T, Yoo HW, Kim BG, Patil MD, Yun H (2018) Biotechnol J 13:1700562

    Article  Google Scholar 

  11. Jang YS, Kim B, Shin JH, Choi YJ, Choi S, Song CW, Lee J, Park HG, Lee SY (2012) Biotechnol Bioeng 109:2437

    Article  CAS  Google Scholar 

  12. Sung S, Jeon H, Sarak S, Ahsan MM, Patil MD, Kroutil W, Kim BG, Yun H (2018) Green Chem 20:4591

    Article  CAS  Google Scholar 

  13. Akhtar MK, Turner NJ, Jones PR (2013) Proc Natl Acad Sci USA 110:87

    Article  CAS  Google Scholar 

  14. Fedorchuk TP, Khusnutdinova AN, Evdokimova E, Flick R, Di Leo R, Stogios P, Savchenko A, Yakunin AF (2020) J Am Chem Soc 142:1038

    Article  CAS  Google Scholar 

  15. Huang L, Sayoga GV, Hollmann F, Kara S (2018) ACS Catal 8:8680

    Article  CAS  Google Scholar 

  16. Versteegen RM, Sijbesma RP, Meijer EW (1999) Angew Chem Int Ed 38:2917

    Article  CAS  Google Scholar 

  17. Vera M, Almontassir A, Rodriguez-Galan A, Puiggali J (2003) Macromolecules 36:9784

    Article  CAS  Google Scholar 

  18. Fernandez CE, Bermudez M, Versteegen RM, Meijer EW, Vancso GJ, Munoz-Guerra S (2010) Eur Polym J 46:2089

    Article  CAS  Google Scholar 

  19. Khusnutdinova AN, Flick R, Popovic A, Brown G, Tchigvintsev A, Nocek B, Correia K, Joo JC, Mahadevan R, Yakunin AF (2017) Biotechnol J 12:1600751

    Article  Google Scholar 

  20. Chung H, Yang JE, Ha JY, Chae TU, Shin JH, Gustavsson M, Lee SY (2015) Curr Opin Biotechnol 36:73

    Article  CAS  Google Scholar 

  21. Napora-Wijata K, Strohmeier GA, Winkler M (2014) Biotechnol J 9:822

    Article  CAS  Google Scholar 

  22. Sasano Y, Nagasawa S, Yamazaki M, Shibuya M, Park J, Iwabuchi Y (2014) Angew Chem Int Ed 53:3236

    Article  CAS  Google Scholar 

  23. Bornscheuer UT, Huisman GW, Kazlauskas RJ, Lutz S, Moore JC, Robins K (2012) Nature 485:185

    Article  CAS  Google Scholar 

  24. Alonso S, Rendueles M, Diaz M (2015) Crit Rev Biotechnol 35:497

    Article  Google Scholar 

  25. Hollmann F, Arends IW, Holtmann D (2011) Green Chem 13:2285

    Article  CAS  Google Scholar 

  26. Mutti FG, Knaus T, Scrutton NS, Breuer M, Turner NJ (2015) Science 349:1525

    Article  CAS  Google Scholar 

  27. Resch V, Fabian WM, Kroutil W (2010) Adv Synth Catal 352:993

    Article  CAS  Google Scholar 

  28. Song JW, Lee JH, Bornscheuer UT, Park JB (2014) Adv Synth Catal 356:1782

    Article  CAS  Google Scholar 

  29. Voss CV, Gruber CC, Faber K, Knaus T, Macheroux P, Kroutil W (2008) J Am Chem Soc 130:13969

    Article  CAS  Google Scholar 

  30. Schrewe M, Ladkau N, Buhler B, Schmid A (2013) Adv Synth Catal 355:1693

    Article  CAS  Google Scholar 

  31. Qu G, Guo J, Yang D, Sun Z (2018) Green Chem 20:777

    Article  CAS  Google Scholar 

  32. Winkler M (2018) Curr Opin Chem Biol 43:23

    Article  CAS  Google Scholar 

  33. Kim GH, Jeon H, Khobragade TP, Patil MD, Sung S, Yoon S, Won Y, Sarak S, Yun H (2019) ChemCatChem 11:1437

    Article  CAS  Google Scholar 

  34. Yoon S, Patil MD, Sarak S, Jeon H, Kim GH, Khobragade TP, Sung S, Yun H (2019) ChemCatChem 11:1898

    Article  CAS  Google Scholar 

  35. Patil MD, Dev MJ, Shinde AS, Bhilare KD, Patel G, Chisti Y, Banerjee UC (2017) Process Biochem 63:113

    Article  CAS  Google Scholar 

  36. Ahsan MM, Patil MD, Jeon H, Sung S, Chung T, Yun H (2018) Catalysts 8:400

    Article  Google Scholar 

  37. Kim GH, Jeon H, Khobragade TP, Patil MD, Sung S, Yoon S, Won Y, Choi IS, Yun H (2019) Enzyme Microb Technol 120:52

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This work was supported by the Ministry of Trade, Industry and Energy of South Korea (MOTIE, South Korea) under the industrial Technology Innovation Program, No. 10062550 and 10076343.The authors also acknowledge the funding from ‘Konkuk University Researcher Fund’ in 2019.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Hyungdon Yun.

Ethics declarations

Conflict of interest

The authors declare no financial or commercial conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 1329 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sarak, S., Jeon, H., Patil, M.D. et al. Enzymatic Synthesis of Aliphatic Primary ω-Amino Alcohols from ω-Amino Fatty Acids by Carboxylic Acid Reductase. Catal Lett 150, 3079–3085 (2020). https://doi.org/10.1007/s10562-020-03233-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-020-03233-9

Keywords

Navigation