Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii

doi:10.1016/j.cjche.2019.12.015

Chinese Journal of Chemical Engineering ›› 2020, Vol. 28 ›› Issue (8): 2160-2166.DOI: 10.1016/j.cjche.2019.12.015

• Biotechnology and Bioengineering • Previous Articles Next Articles

Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii

Han Zu¹, Hui Zhang¹, Anwen Fan¹, Jie Gu¹, Yao Nie¹, Pengjie Luo³, Yan Xu^1,2

1 School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education, Jiangnan University, Wuxi 214122, China;
2 State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China;
3 China National Center for Food Safety Risk Assessment, NHC Key Laboratory of Food Safety Risk Assessment, Beijing 100022, China

Received:2019-09-05 Revised:2019-11-12 Online:2020-09-19 Published:2020-08-28
Contact: Yao Nie, Pengjie Luo
Supported by:
Financial supports from the National Key R&D Program of China (2018YFC1604100), the National Natural Science Foundation of China (NSFC)[21676120, 31872891], the 111 Project[111-2-06], the Highend Foreign Experts Recruitment Program[G20190010083], the Program for Advanced Talents within Six Industries of Jiangsu Province[2015-NY-007], the National Program for Support of Top-notch Young Professionals, the Fundamental Research Funds for the Central Universities[JUSRP51504], the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, Top-notch Academic Programs Project of Jiangsu Higher Education Institutions, the Jiangsu Province "Collaborative Innovation Center for Advanced Industrial Fermentation" Industry Development Program, and the National First-Class Discipline Program of Light Industry Technology and Engineering[LITE2018-09] are greatly appreciated. We would like to thank Editage (www.editage.cn) for English language editing.

Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii

Han Zu¹, Hui Zhang¹, Anwen Fan¹, Jie Gu¹, Yao Nie¹, Pengjie Luo³, Yan Xu^1,2

1 School of Biotechnology and Key Laboratory of Industrial Biotechnology of Ministry of Education, Jiangnan University, Wuxi 214122, China;
2 State Key Laboratory of Food Science and Technology, Jiangnan University, Wuxi 214122, China;
3 China National Center for Food Safety Risk Assessment, NHC Key Laboratory of Food Safety Risk Assessment, Beijing 100022, China

通讯作者: Yao Nie, Pengjie Luo
基金资助:
Financial supports from the National Key R&D Program of China (2018YFC1604100), the National Natural Science Foundation of China (NSFC)[21676120, 31872891], the 111 Project[111-2-06], the Highend Foreign Experts Recruitment Program[G20190010083], the Program for Advanced Talents within Six Industries of Jiangsu Province[2015-NY-007], the National Program for Support of Top-notch Young Professionals, the Fundamental Research Funds for the Central Universities[JUSRP51504], the Project Funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions, Top-notch Academic Programs Project of Jiangsu Higher Education Institutions, the Jiangsu Province "Collaborative Innovation Center for Advanced Industrial Fermentation" Industry Development Program, and the National First-Class Discipline Program of Light Industry Technology and Engineering[LITE2018-09] are greatly appreciated. We would like to thank Editage (www.editage.cn) for English language editing.

Abstract

Abstract: (R)-1,3-butanediol is an important pharmaceutical intermediate, and the synthesis of (R)-1,3-butanediol using green biological methods has recently been of interest for industrial application. Here, a novel strain QC-1 that efficiently transforms 4-hydroxy-2-butanone to (R)-1,3-butanediol was isolated from soil samples. Based on morphological, physiological, and biochemical tests and 5.8S-internal transcribed spacer sequencing, the strain was identified as Pichia kudriavzevii QC-1. The reaction conditions were optimized to 35 ℃, pH 8.0, rotation speed 200 rpm, and 6:5 mass ratio of glucose to 4-hydroxy-2-butanone. Evaluation of the effects of 4-hydroxy- 2-butanone concentrations on yield and cell survival rate showed that 85.60 g·L^-1 product accumulated, with an enantiomeric excess of more than 99%, when 30 g·L^-1 4-hydroxy-2-butanone was added at 0, 10, and 30 h in a 3-L bioreactor. Thus, strain QC-1 showed excellent catalytic activity and stereoselectivity for the synthesis of (R)-1,3-butanediol from 4-hydroxy-2-butanone.

Key words: Asymmetric reduction, Stereoselectivity, (R)-1,3-butanediol, 4-Hydroxy-2-butanone, Whole-cell catalysis

摘要： (R)-1,3-butanediol is an important pharmaceutical intermediate, and the synthesis of (R)-1,3-butanediol using green biological methods has recently been of interest for industrial application. Here, a novel strain QC-1 that efficiently transforms 4-hydroxy-2-butanone to (R)-1,3-butanediol was isolated from soil samples. Based on morphological, physiological, and biochemical tests and 5.8S-internal transcribed spacer sequencing, the strain was identified as Pichia kudriavzevii QC-1. The reaction conditions were optimized to 35 ℃, pH 8.0, rotation speed 200 rpm, and 6:5 mass ratio of glucose to 4-hydroxy-2-butanone. Evaluation of the effects of 4-hydroxy- 2-butanone concentrations on yield and cell survival rate showed that 85.60 g·L^-1 product accumulated, with an enantiomeric excess of more than 99%, when 30 g·L^-1 4-hydroxy-2-butanone was added at 0, 10, and 30 h in a 3-L bioreactor. Thus, strain QC-1 showed excellent catalytic activity and stereoselectivity for the synthesis of (R)-1,3-butanediol from 4-hydroxy-2-butanone.

关键词: Asymmetric reduction, Stereoselectivity, (R)-1,3-butanediol, 4-Hydroxy-2-butanone, Whole-cell catalysis

Han Zu, Hui Zhang, Anwen Fan, Jie Gu, Yao Nie, Pengjie Luo, Yan Xu. Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii[J]. Chinese Journal of Chemical Engineering, 2020, 28(8): 2160-2166.

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Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii

Highly efficient synthesis of (R)-1,3-butanediol via anti-Prelog reduction of 4-hydroxy-2-butanone with absolute stereoselectivity by a newly isolated Pichia kudriavzevii

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