Double substituted variant of Bacillus amyloliquefaciens esterase with enhanced enantioselectivity and high activity towards 1-(3′,4′-methylenedioxyphenyl)ethyl acetate

Verfasser / Beitragende:
[Jia-Yan Liu, Han-Ping Bian, Yun Tang, Yun-Peng Bai, Jian-He Xu]
Ort, Verlag, Jahr:
2015
Enthalten in:
Applied Microbiology and Biotechnology, 99/4(2015-02-01), 1701-1708
Format:
Artikel (online)
ID: 605503850
LEADER caa a22 4500
001 605503850
003 CHVBK
005 20210128100613.0
007 cr unu---uuuuu
008 210128e20150201xx s 000 0 eng
024 7 0 |a 10.1007/s00253-014-5992-0  |2 doi 
035 |a (NATIONALLICENCE)springer-10.1007/s00253-014-5992-0 
245 0 0 |a Double substituted variant of Bacillus amyloliquefaciens esterase with enhanced enantioselectivity and high activity towards 1-(3′,4′-methylenedioxyphenyl)ethyl acetate  |h [Elektronische Daten]  |c [Jia-Yan Liu, Han-Ping Bian, Yun Tang, Yun-Peng Bai, Jian-He Xu] 
520 3 |a Bacillus amyloliquefaciens esterase (BAE) was applied to produce (R)-1-(3′,4′-methylenedioxyphenyl)ethanol, a chiral drug intermediate. In this study, we improved the enantioselectivity of BAE by protein engineering instead of process engineering as used in our previous work. Saturation mutagenesis was carried out on eight positions of BAE based on structure modeling and substrate docking. A double substituted variant V10 (K358D/A396C) showed an excellent enantioselectivity without decreasing the activity. The functions of these two mutations (K358D and A396C) were investigated, revealing a synergic effect on the BAE enantioselectivity. Using the variant V10, enantiopure (R)-1-(3′,4′-methylenedioxyphenyl)ethanol could be readily prepared in >97% ee, affording a high space-time yield (123gL−1 day−1) and a high ratio of substrate/catalyst (40gg−1) in 1-L reaction. 
540 |a Springer-Verlag Berlin Heidelberg, 2014 
690 7 |a Bacillus amyloliquefaciens  |2 nationallicence 
690 7 |a Esterase  |2 nationallicence 
690 7 |a Enantioselectivity  |2 nationallicence 
690 7 |a Iterative saturation mutagenesis  |2 nationallicence 
690 7 |a 1-(3′,4′-Methylenedioxyphenyl)ethanol  |2 nationallicence 
700 1 |a Liu  |D Jia-Yan  |u State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
700 1 |a Bian  |D Han-Ping  |u Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
700 1 |a Tang  |D Yun  |u Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
700 1 |a Bai  |D Yun-Peng  |u State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
700 1 |a Xu  |D Jian-He  |u State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
773 0 |t Applied Microbiology and Biotechnology  |d Springer Berlin Heidelberg  |g 99/4(2015-02-01), 1701-1708  |x 0175-7598  |q 99:4<1701  |1 2015  |2 99  |o 253 
856 4 0 |u https://doi.org/10.1007/s00253-014-5992-0  |q text/html  |z Onlinezugriff via DOI 
898 |a BK010053  |b XK010053  |c XK010000 
900 7 |a Metadata rights reserved  |b Springer special CC-BY-NC licence  |2 nationallicence 
908 |D 1  |a research-article  |2 jats 
949 |B NATIONALLICENCE  |F NATIONALLICENCE  |b NL-springer 
950 |B NATIONALLICENCE  |P 856  |E 40  |u https://doi.org/10.1007/s00253-014-5992-0  |q text/html  |z Onlinezugriff via DOI 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Liu  |D Jia-Yan  |u State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Bian  |D Han-Ping  |u Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Tang  |D Yun  |u Shanghai Key Laboratory of New Drug Design, School of Pharmacy, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Bai  |D Yun-Peng  |u State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
950 |B NATIONALLICENCE  |P 700  |E 1-  |a Xu  |D Jian-He  |u State Key Laboratory of Bioreactor Engineering, East China University of Science and Technology, 130 Meilong Road, 200237, Shanghai, China  |4 aut 
950 |B NATIONALLICENCE  |P 773  |E 0-  |t Applied Microbiology and Biotechnology  |d Springer Berlin Heidelberg  |g 99/4(2015-02-01), 1701-1708  |x 0175-7598  |q 99:4<1701  |1 2015  |2 99  |o 253