Chem. J. Chinese Universities ›› 2020, Vol. 41 ›› Issue (5): 1018.doi: 10.7503/cjcu20190621
• Organic Chemistry • Previous Articles Next Articles
WU Tao1,2,MU Xiaoqing1,2,*(),NIE Yao1,XU Yan1
Received:
2019-12-02
Online:
2020-05-10
Published:
2020-02-07
Contact:
Xiaoqing MU
E-mail:xqmu@jiangnan.edu.cn
Supported by:
CLC Number:
TrendMD:
WU Tao,MU Xiaoqing,NIE Yao,XU Yan. Improving Catalytic Efficiency of Bacillus Cereus Amine Dehydrogenase for Acetophenone Reduction by Iterative Saturation Mutagenesis [J]. Chem. J. Chinese Universities, 2020, 41(5): 1018.
Mutant | Acetophenone | NADH | ||||
---|---|---|---|---|---|---|
Km/ (mmol·L-1) | kcat/ min-1 | (kcat/Km)/ (L·min-1·mmol-1) | Km/ (mmol·L-1) | kcat/ min-1 | (kcat/Km)/ (L·min-1·mmol-1) | |
BcAmDH | 31.11±1.74 | 9.58±0.51 | 0.31 | 0.026±0.0025 | 4.13±0.32 | 158.85 |
V293A | 36.18±1.65 | 26.02±1.48 | 0.72 | 0.031±0.0023 | 8.77±0.76 | 282.90 |
V293A/E116V | 31.52±1.92 | 44.89±3.37 | 1.42 | 0.028±0.0034 | 16.09±0.97 | 574.64 |
V293A/E116V/T136S | 28.87±1.22 | 73.25±6.21 | 2.54 | 0.027±0.0031 | 21.14±1.31 | 782.96 |
Mutant | Acetophenone | NADH | ||||
---|---|---|---|---|---|---|
Km/ (mmol·L-1) | kcat/ min-1 | (kcat/Km)/ (L·min-1·mmol-1) | Km/ (mmol·L-1) | kcat/ min-1 | (kcat/Km)/ (L·min-1·mmol-1) | |
BcAmDH | 31.11±1.74 | 9.58±0.51 | 0.31 | 0.026±0.0025 | 4.13±0.32 | 158.85 |
V293A | 36.18±1.65 | 26.02±1.48 | 0.72 | 0.031±0.0023 | 8.77±0.76 | 282.90 |
V293A/E116V | 31.52±1.92 | 44.89±3.37 | 1.42 | 0.028±0.0034 | 16.09±0.97 | 574.64 |
V293A/E116V/T136S | 28.87±1.22 | 73.25±6.21 | 2.54 | 0.027±0.0031 | 21.14±1.31 | 782.96 |
[1] |
Tseliou V., Knaus T., Masman M. F., Corrado M. L., Mutti F. G., Nat. Commun., 2019,10(1), 1—11
doi: 10.1038/s41467-018-07882-8 URL pmid: 30602773 |
[2] |
Jann M. W., Pharmacotherapy, 2000,20(1), 1—12
doi: 10.1592/phco.20.1.1.34664 URL pmid: 10641971 |
[3] | Zhang H ., The Preparation and Analysis of α-Phenylethylamine, Sichuan University, Chengdu, 2004 |
( 张华 . 手性物α-苯乙胺的制备和分析研究, 成都: 四川大学, 2004) | |
[4] |
Tan X., Gao S., Zeng W., Xin S., Yin Q., Zhang X ., J. Am. Chem. Soc., 2018,140(6), 2024—2027
doi: 10.1021/jacs.7b12898 URL pmid: 29377687 |
[5] | Hoben C. E., Tetrahedron Lett., 2008,49(6), 977—979 |
[6] |
Parvulescu A. N., Jacobs P. A., Vos D. E., Chem. Eur. J., 2010,13(7), 2034—2043
doi: 10.1002/chem.200600899 URL pmid: 17152100 |
[7] | Allwein S. P., McWilliams J. C., Secord E. A., Mowrey D. R., Nelson T. D., Kress M. H., Tetrahedron Lett., 2006,47(36), 6409—6412 |
[8] | Torres Gavilán A., Escalante J., Regla I., López Munguía A., Castillo E ., Tetrahedron: Asymmetry, 2007,18(22), 2621—2624 |
[9] | Falus P. D., Boros Z., Hornyánszky G., Nagy J., Darvas F., Ürge L., Poppe L., Stud. U. Babes-Bol. Che., 2010,55(4), 289—296 |
[10] | Leisch H., Grosse S., Iwaki H., Hasegawa Y., Lau P. C., Can. J. Chem., 2011,90(1), 39—45 |
[11] | Fesko K., Steiner K., Breinbauer R., Schwab H., Schürmann M., Strohmeier G. A., J. Mol. Catal. B: Enzym., 2013,96, 103—110 |
[12] | Malik M. S., Park E. S., Shin J. S., Green Chem., 2012,14(8), 2137—2140 |
[13] | Ye L. J., Toh H. H., Yang Y., Adams J. P., Snajdrova R., Li Z., ACS Catal., 2015,5(2), 1119—1122 |
[14] | Abrahamson M. J., Wong J. W., Bommarius A. S., Adv. Synth. Catal., 2013,355(9), 1780—1786 |
[15] |
Knaus T., Böhmer W., Mutti F. G., Green Chem., 2017,19(2), 453—463
doi: 10.1039/C6GC01987K URL pmid: 28663713 |
[16] | Au S. K., Bommarius B. R., Bommarius A. S., ACS Catal., 2014,4(11), 4021—4026 |
[17] | Mayol O., David S., Darii E., Debard A., Mariage A., Pellouin V., Petit J. L., Salanoubat M., Berardinis V., Zaparucha A., Catal. Sci. Technol., 2016,6(20), 7421—7428 |
[18] | Itoh N., Yachi C., Kudome T ., J. Mol. Catal. B: Enzym., 2000,10(1—3), 281—290 |
[19] |
Abrahamson M. J., Vázquez F. E., Woodall N. B., Moore J. C., Bommarius A. S., Angew. Chem. Int. Ed., 2012,51(16), 3969—3972
doi: 10.1002/anie.201107813 URL pmid: 22396126 |
[20] | Chen F. F., Liu Y. Y., Zheng G. W., Xu J. H., ChemCatChem, 2015,7(23), 3838—3841 |
[21] |
Löwe J., Ingram A. A., Gröger H., Biorg. Med. Chem., 2018,26(7), 1387—1392
doi: 10.1016/j.bmc.2017.12.005 URL pmid: 29548785 |
[22] |
Bommarius B. R., Schürmann M., Bommarius A. S., Chem. Commun., 2014,50(95), 14953—14955
doi: 10.1039/c4cc06527a URL pmid: 25347124 |
[23] |
Chen F. F., Zheng G. W., Liu L., Li H., Chen Q., Li F. L., Li C. X., Xu J. H., ACS Catal., 2018,8(3), 2622—2628
doi: 10.1021/acscatal.7b04135 URL |
[24] |
Yamaguchi H., Kamegawa A., Nakata K., Kashiwagi T., Mizukoshi T., Fujiyoshi Y., Tani K ., J. Struct. Biol., 2019,205(1), 11—21
doi: 10.1016/j.jsb.2018.12.001 URL pmid: 30543982 |
[25] |
Waterhouse A., Bertoni M., Bienert S., Studer G., Tauriello G., Gumienny R., Heer F. T., Beer T. A. P., Rempfer C., Bordoli L., Nucleic Acids Res., 2018,46(W1), W296—W303
doi: 10.1093/nar/gky427 URL pmid: 29788355 |
[26] |
Lenka S., Jan S., Tomas M., David B., Jiri D., Nucleic Acids Res., 2018,46(W1), W356—W362
doi: 10.1093/nar/gky417 URL pmid: 29796670 |
[27] |
Wei T., Chang C., Xue L., Zhao J., Jie L., Nucleic Acids Res., 2018,46(W1), W363—W367
doi: 10.1093/nar/gky473 URL pmid: 29860391 |
[28] | Yin X., Liu Y., Meng L., Zhou H., Wu J., Yang L., Adv. Synth. Catal, 2019,361(4), 803—812 |
[29] | Rao L., Bi Y. F., Qiu X. G., Zhang F., Wang Y., Cao S. G., Chem. Res. Chinese Universities, 2009,25(3), 353—356 |
[30] | Zhou J., Xu G., Han R., Dong J., Zhang W., Zhang R., Ni Y., Catal. Sci. Technol, 2016,6(16), 6320—6327 |
[31] |
Sun Z. T., Lonsdale R., Kong X. D., Xu J. H., Zhou J. H., Reetz M. T., Angew. Chem. Int. Ed., 2015,54(42), 12410—12415
doi: 10.1002/anie.201501809 URL pmid: 25891639 |
[32] |
Reetz M. T., Kahakeaw D., Sanchis J., Mol. Biosyst., 2009,5(2), 115—122
doi: 10.1039/b814862g URL pmid: 19156255 |
[33] |
Luo X., Wang Y. J., Shen W., Zheng Y. G., J. Biotechnol., 2016,224, 20—26
doi: 10.1016/j.jbiotec.2016.03.008 URL pmid: 26959479 |
[34] | Huang L., Ma H. M., Yu H. L., Xu J. H., Adv. Synth. Catal., 2014,356(9), 1943—1948 |
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