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1

Sehl, Torsten, Saskia Bock, Lisa Marx, Zaira Maugeri, Lydia Walter, Robert Westphal, Constantin Vogel et al. "Asymmetric synthesis of (S)-phenylacetylcarbinol – closing a gap in C–C bond formation". Green Chemistry 19, n. 2 (2017): 380–84. http://dx.doi.org/10.1039/c6gc01803c.

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Abstract (sommario):
By the combination of biocatalyst design and reaction engineering, the so far not stereoselectively accessible (S)-phenylacetylcarbinol could be enzymatically synthesized with product concentrations >48 g L−1 and an enantiomeric excess up to 97%.
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2

Tripathi, Chandrakant M., Suresh C. Agarwal e Samar K. Basu. "Production of l-phenylacetylcarbinol by fermentation". Journal of Fermentation and Bioengineering 84, n. 6 (gennaio 1997): 487–92. http://dx.doi.org/10.1016/s0922-338x(97)81900-9.

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3

B., Rosche, Leksawasdi N., Sandford V., Breuer M., Hauer B. e Rogers P. "Enzymatic ( R )-phenylacetylcarbinol production in benzaldehyde emulsions". Applied Microbiology and Biotechnology 60, n. 1-2 (1 ottobre 2002): 94–100. http://dx.doi.org/10.1007/s00253-002-1084-7.

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4

Doostmohammadi, Mohsen, Mohammad Ali Asadollahi, Iraj Nahvi, Davoud Biria, Gholam Reza Ghezelbash e Maryam Kheyrandish. "L-phenylacetylcarbinol production by yeast petite mutants". Annals of Microbiology 66, n. 3 (20 gennaio 2016): 1049–55. http://dx.doi.org/10.1007/s13213-015-1190-2.

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5

Harini, Madakashira, Jhumpa Adhikari e K. Yamuna Rani. "Prediction of vapour–liquid coexistence data of Phenylacetylcarbinol". Fluid Phase Equilibria 364 (febbraio 2014): 6–14. http://dx.doi.org/10.1016/j.fluid.2013.11.044.

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6

Liew, Michelle K. H., Anthony G. Fane e Peter L. Rogers. "Applicability of continuous membrane bioreactor in production of phenylacetylcarbinol". Journal of Chemical Technology AND Biotechnology 64, n. 2 (ottobre 1995): 200–206. http://dx.doi.org/10.1002/jctb.280640214.

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7

Rosche, Bettina, Vanessa Sandford, Michael Breuer, Bernhard Hauer e Peter L. Rogers. "Enhanced production of R-phenylacetylcarbinol (R-PAC) through enzymatic biotransformation". Journal of Molecular Catalysis B: Enzymatic 19-20 (dicembre 2002): 109–15. http://dx.doi.org/10.1016/s1381-1177(02)00157-1.

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8

Engel, Stanislav, Maria Vyazmensky, Shimona Geresh, Ze'ev Barak e David M. Chipman. "Acetohydroxyacid synthase: A new enzyme for chiral synthesis ofR-phenylacetylcarbinol". Biotechnology and Bioengineering 83, n. 7 (24 luglio 2003): 833–40. http://dx.doi.org/10.1002/bit.10728.

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9

Park, Joong Kon, e Kwang Deok Lee. "Production of L-phenylacetylcarbinol (L-PAC) by encapsulatedSaccharomyces cerevisiae cells". Korean Journal of Chemical Engineering 18, n. 3 (maggio 2001): 363–70. http://dx.doi.org/10.1007/bf02699179.

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10

Breuer, Michael, Martina Pohl, Bernhard Hauer e Bettina Lingen. "High-throughput assay of ( R )-phenylacetylcarbinol synthesized by pyruvate decarboxylase". Analytical and Bioanalytical Chemistry 374, n. 6 (1 novembre 2002): 1069–73. http://dx.doi.org/10.1007/s00216-002-1579-1.

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11

Gunawan, Cindy, Gernalia Satianegara, Allen K. Chen, Michael Breuer, Bernhard Hauer, Peter L. Rogers e Bettina Rosche. "Yeast pyruvate decarboxylases: variation in biocatalytic characteristics for (R)-phenylacetylcarbinol production". FEMS Yeast Research 7, n. 1 (gennaio 2007): 33–39. http://dx.doi.org/10.1111/j.1567-1364.2006.00138.x.

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12

Leksawasdi, Noppol, Yvonne Y. S. Chow, Michael Breuer, Bernhard Hauer, Bettina Rosche e Peter L. Rogers. "Kinetic analysis and modelling of enzymatic (R)-phenylacetylcarbinol batch biotransformation process". Journal of Biotechnology 111, n. 2 (luglio 2004): 179–89. http://dx.doi.org/10.1016/j.jbiotec.2004.04.001.

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13

Yun, Hyungdon, e Byung-Gee Kim. "Enzymatic production of (R)-phenylacetylcarbinol by pyruvate decarboxylase from Zymomonas mobilis". Biotechnology and Bioprocess Engineering 13, n. 3 (giugno 2008): 372–76. http://dx.doi.org/10.1007/s12257-008-0030-7.

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14

Maroney, Kerrie Anne N., Peter N. Culshaw, Urs D. Wermuth e Sarah L. Cresswell. "Investigation of the l-phenylacetylcarbinol process to substituted benzaldehydes of interest". Forensic Science International 235 (febbraio 2014): 52–61. http://dx.doi.org/10.1016/j.forsciint.2013.11.017.

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15

K, Suresh, Harisaranraj R, Saravanababu S e Vaira achudhan V. "Byconversion Of Benzaldehyde Into (R)-Phenylacetylcarbinol By Hansenulla Polymorpha And Brettanomyces Lambicus". International Journal on Applied Bio-Engineering 4, n. 1 (2010): 40–45. http://dx.doi.org/10.18000/ijabeg.10058.

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16

Oliver, A. L., F. A. Roddick e B. N. Anderson. "Cleaner production of phenylacetylcarbinol by yeast through productivity improvements and waste minimiaation". Pure and Applied Chemistry 69, n. 11 (1 gennaio 1997): 2371–86. http://dx.doi.org/10.1351/pac199769112371.

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17

B., Rosche, Sandford V., Breuer M., Hauer B. e Rogers P. "Biotransformation of benzaldehyde into ( R )-phenylacetylcarbinol by filamentous fungi or their extracts". Applied Microbiology and Biotechnology 57, n. 3 (1 ottobre 2001): 309–15. http://dx.doi.org/10.1007/s002530100781.

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18

Seifi, Mohammad Mahdi, Elham Iranmanesh, Mohammad Ali Asadollahi e Ayyoob Arpanaei. "Biotransformation of benzaldehyde into l-phenylacetylcarbinol using magnetic nanoparticles-coated yeast cells". Biotechnology Letters 42, n. 4 (16 gennaio 2020): 597–603. http://dx.doi.org/10.1007/s10529-020-02798-0.

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19

Iwan, Peter, Günter Goetz, Susanne Schmitz, Bernhard Hauer, Michael Breuer e Martina Pohl. "Studies on the continuous production of (R)-(−)-phenylacetylcarbinol in an enzyme-membrane reactor". Journal of Molecular Catalysis B: Enzymatic 11, n. 4-6 (gennaio 2001): 387–96. http://dx.doi.org/10.1016/s1381-1177(00)00029-1.

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20

Satianegara, Gernalia, Michael Breuer, Bernhard Hauer, Peter L. Rogers e Bettina Rosche. "Enzymatic (R)-phenylacetylcarbinol production in a benzaldehyde emulsion system with Candida utilis cells". Applied Microbiology and Biotechnology 70, n. 2 (marzo 2006): 170–75. http://dx.doi.org/10.1007/s00253-005-0063-1.

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21

Iranmanesh, Elham, Mohammad Ali Asadollahi e Davoud Biria. "Improving l-phenylacetylcarbinol production in Saccharomyces cerevisiae by in silico aided metabolic engineering". Journal of Biotechnology 308 (gennaio 2020): 27–34. http://dx.doi.org/10.1016/j.jbiotec.2019.11.008.

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22

Andreu, Cecilia, e Marcel ·lí del Olmo. "Biotransformation using halotolerant yeast in seawater: a sustainable strategy to produce R-(−)-phenylacetylcarbinol". Applied Microbiology and Biotechnology 102, n. 11 (7 aprile 2018): 4717–27. http://dx.doi.org/10.1007/s00253-018-8945-1.

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23

Shin, Hyoun S., e Peter L. Rogers. "Production of L-phenylacetylcarbinol (L-PAC) from benzaldehyde using partially purified pyruvate decarboxylase (PDC)". Biotechnology and Bioengineering 49, n. 1 (26 marzo 2000): 52–62. http://dx.doi.org/10.1002/(sici)1097-0290(19960105)49:1<52::aid-bit7>3.0.co;2-s.

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24

Zhang, Wenzhi, Zhilong Wang, Wei Li, Baohua Zhuang e Hanshi Qi. "Production of l-phenylacetylcarbinol by microbial transformation in polyethylene glycol-induced cloud point system". Applied Microbiology and Biotechnology 78, n. 2 (febbraio 2008): 233–39. http://dx.doi.org/10.1007/s00253-007-1304-2.

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25

Leksawasdi, Noppol, Bettina Rosche e Peter L. Rogers. "Mathematical model for kinetics of enzymatic conversion of benzaldehyde and pyruvate to (R)-phenylacetylcarbinol". Biochemical Engineering Journal 23, n. 3 (maggio 2005): 211–20. http://dx.doi.org/10.1016/j.bej.2004.11.001.

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26

Bruder, Stefan, e Eckhard Boles. "Improvement of the yeast based (R)-phenylacetylcarbinol production process via reduction of by-product formation". Biochemical Engineering Journal 120 (aprile 2017): 103–12. http://dx.doi.org/10.1016/j.bej.2016.09.021.

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27

Shin, Hyoun S., e Peter L. Rogers. "Kinetic evaluation of biotransformation of benzaldehyde to L-phenylacetylcarbinol by immobilized pyruvate decarboxylase from Candida utilis". Biotechnology and Bioengineering 49, n. 4 (26 marzo 2000): 429–36. http://dx.doi.org/10.1002/(sici)1097-0290(19960220)49:4<429::aid-bit10>3.0.co;2-5.

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28

Khan, Tanya R., e Andrew J. Daugulis. "Application of solid-liquid TPPBs to the production of L-phenylacetylcarbinol from benzaldehyde using Candida utilis". Biotechnology and Bioengineering 107, n. 4 (15 giugno 2010): 633–41. http://dx.doi.org/10.1002/bit.22839.

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29

Sandford, Vanessa, Michael Breuer, Bernhard Hauer, Peter Rogers e Bettina Rosche. "(R)-phenylacetylcarbinol production in aqueous/organic two-phase systems using partially purified pyruvate decarboxylase fromCandida utilis". Biotechnology and Bioengineering 91, n. 2 (2005): 190–98. http://dx.doi.org/10.1002/bit.20513.

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30

Shin, H. S., e P. L. Rogers. "Biotransformation of benzeldehyde to L -phenylacetylcarbinol, an intermediate in L -ephedrine production, by immobilized Candida utilis". Applied Microbiology and Biotechnology 44, n. 1-2 (11 dicembre 1995): 7–14. http://dx.doi.org/10.1007/s002530050512.

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31

Mahendran, Prabhu, A. Jeya Rajendran, C. Balachandran, A. Stalin, Saravanan Rangan, Loganathan Kothandapani, Kella Chennakesava Rao, Suresh Awale e B. N. Hiteshkumar. "Synthesis of novel β-amino alcohols from phenylacetylcarbinol: cytotoxicity activity against A549 cells and molecular docking". Research on Chemical Intermediates 44, n. 1 (4 settembre 2017): 535–52. http://dx.doi.org/10.1007/s11164-017-3118-x.

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32

Shin, H. S., e P. L. Rogers. "Biotransformation of benzeldehyde to l-phenylacetylcarbinol, an intermediate in l-ephedrine production, by immobilized Candida utilis". Applied Microbiology and Biotechnology 44, n. 1-2 (dicembre 1995): 7–14. http://dx.doi.org/10.1007/bf00164473.

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33

Shukla, Vilas B., Virendra R. Madyar, Bhushan M. Khadilkar e Pushpa R. Kulkarni. "Biotransformation of benzaldehyde toL-phenylacetylcarbinol (L-PAC) byTorulaspora delbrueckii and conversion to ephedrine by microwave radiation". Journal of Chemical Technology & Biotechnology 77, n. 2 (2002): 137–40. http://dx.doi.org/10.1002/jctb.534.

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34

Sahm, Hermann. "Acetoin and Phenylacetylcarbinol Formation by the Pyruvate Decarboxylases of Zymomonas Mobilis and Saccharomyces Carlsbergensis Stephanie Bringer-Meyer". Biocatalysis 1, n. 4 (gennaio 1988): 321–31. http://dx.doi.org/10.3109/10242428808998172.

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35

Leksawasdi, Noppol, Peter L. Rogers e Bettina Rosche. "Improved enzymatic two-phase biotransformation for (R)-phenylacetylcarbinol: Effect of dipropylene glycol and modes of pH control". Biocatalysis and Biotransformation 23, n. 6 (gennaio 2005): 445–51. http://dx.doi.org/10.1080/10242420500444135.

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36

Rosche, Bettina, Michael Breuer, Bernhard Hauer e Peter L. Rogers. "Cells of Candida utilis for in vitro (R)-phenylacetylcarbinol production in an aqueous/octanol two-phase reactor". Biotechnology Letters 27, n. 8 (aprile 2005): 575–81. http://dx.doi.org/10.1007/s10529-005-3252-1.

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37

Gunawan, Cindy, Michael Breuer, Bernhard Hauer, Peter L. Rogers e Bettina Rosche. "Improved (R)-phenylacetylcarbinol production with Candida utilis pyruvate decarboxylase at decreased organic to aqueous phase volume ratios". Biotechnology Letters 30, n. 2 (18 settembre 2007): 281–86. http://dx.doi.org/10.1007/s10529-007-9525-0.

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38

Shukla, Vilas B., e Pushpa R. Kulkarni. "Biotransformation of Benzaldehyde to L-Phenylacetylcarbinol (L-PAC) by Free Cells of Torulaspora delbrueckii in presence of Beta-Cyclodextrin". Brazilian Archives of Biology and Technology 45, n. 3 (settembre 2002): 265–68. http://dx.doi.org/10.1590/s1516-89132002000300003.

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39

Satianegara, Gernalia, Peter L. Rogers e Bettina Rosche. "Comparative studies on enzyme preparations and role of cell components for (R)-phenylacetylcarbinol production in a two-phase biotransformation". Biotechnology and Bioengineering 94, n. 6 (2006): 1189–95. http://dx.doi.org/10.1002/bit.20959.

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40

Goetz, G�nter, Peter Iwan, Bernhard Hauer, Michael Breuer e Martina Pohl. "Continuous production of (R)-phenylacetylcarbinol in an enzyme-membrane reactor using a potent mutant of pyruvate decarboxylase fromZymomonas mobilis". Biotechnology and Bioengineering 74, n. 4 (2001): 317–25. http://dx.doi.org/10.1002/bit.1122.

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41

Alvarado, Omar, Rafael García-Meseguer, Jose Javier Ruiz-Pernía, Iñaki Tuñon e Eduardo J. Delgado. "Mechanistic study of the biosynthesis of R-phenylacetylcarbinol by acetohydroxyacid synthase enzyme using hybrid quantum mechanics/molecular mechanics simulations". Archives of Biochemistry and Biophysics 707 (agosto 2021): 108849. http://dx.doi.org/10.1016/j.abb.2021.108849.

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42

Shukla, Vilas B., e Pushpa R. Kulkarni. "Comparative studies on bioconversion of benzaldehyde toL-phenylacetylcarbinol (L-PAC) using calcium alginate- and barium alginate-immobilized cells ofTorulaspora delbrueckii". Journal of Chemical Technology & Biotechnology 78, n. 9 (2003): 949–51. http://dx.doi.org/10.1002/jctb.863.

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43

Nunta, Rojarej, Charin Techapun, Ampin Kuntiya, Prasert Hanmuangjai, Churairat Moukamnerd, Julaluk Khemacheewakul, Sumeth Sommanee, Alissara Reungsang, Mallika Boonmee Kongkeitkajorn e Noppol Leksawasdi. "Ethanol and phenylacetylcarbinol production processes of Candida tropicalis TISTR 5306 and Saccharomyces cerevisiae TISTR 5606 in fresh juices from longan fruit of various sizes". Journal of Food Processing and Preservation 42, n. 11 (21 ottobre 2018): e13815. http://dx.doi.org/10.1111/jfpp.13815.

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44

Khan, Tanya R., e Andrew J. Daugulis. "The effects of polymer phase ratio and feeding strategy on solid–liquid TPPBs for the production of l-phenylacetylcarbinol from benzaldehyde using Candida utilis". Biotechnology Letters 33, n. 1 (29 settembre 2010): 63–70. http://dx.doi.org/10.1007/s10529-010-0408-4.

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45

Wang, Zhilong, Rui Liang, Jian-He Xu, Yubo Liu e Hanshi Qi. "A Closed Concept of Extractive Whole Cell Microbial Transformation of Benzaldehyde into l-Phenylacetylcarbinol by Saccharomyces cerevisiae in Novel Polyethylene-Glycol-Induced Cloud-Point System". Applied Biochemistry and Biotechnology 160, n. 6 (27 giugno 2009): 1865–77. http://dx.doi.org/10.1007/s12010-009-8695-8.

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46

Alvarado, Omar, Rafael García-Meseguer, Jose Javier Ruiz-Pernía, Iñaki Tuñon e Eduardo J. Delgado. "Corrigendum to “Mechanistic study of the biosynthesis of R-phenylacetylcarbinol by acetohydroxyacid synthase enzyme using hybrid quantum mechanics/molecular mechanics simulations” [Arch. Biochem. Biophys. 701 (2021) 108807]". Archives of Biochemistry and Biophysics 707 (agosto 2021): 108848. http://dx.doi.org/10.1016/j.abb.2021.108848.

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47

Andreu, Cecilia, e Marcel·lí del Olmo. "Potential of some yeast strains in the stereoselective synthesis of (R)-(−)-phenylacetylcarbinol and (S)-(+)-phenylacetylcarbinol and their reduced 1,2-dialcohol derivatives". Applied Microbiology and Biotechnology, 27 marzo 2014. http://dx.doi.org/10.1007/s00253-014-5635-5.

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48

Liang, Yan-Fei, Le-Tian Yan, Qiao Yue, Ji-Kui Zhao, Cai-Yun Luo, Feng Gao, Heng Li e Wen-Yun Gao. "Preparation of a whole cell catalyst overexpressing acetohydroxyacid synthase of Thermotoga maritima and its application in the syntheses of α-hydroxyketones". Scientific Reports 10, n. 1 (21 settembre 2020). http://dx.doi.org/10.1038/s41598-020-72416-6.

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Abstract The large catalytic subunit of acetohydroxyacid synthase (AHAS, EC 2.2.1.6) of Thermotoga maritima (TmcAHAS) was prepared in this study. It possesses high specific activity and excellent stability. The protein and a whole cell catalyst overexpressing the protein were applied to the preparation of α-hydroxyketones including acetoin (AC), 3-hydroxy-2-pentanone (HP), and (R)-phenylacetylcarbinol (R-PAC). The results show that AC and HP could be produced in high yields (84% and 62%, respectively), while R-PAC could be synthesized in a high yield (about 78%) with an R/S ratio of 9:1. Therefore, TmcAHAS and the whole cell catalyst overexpressing the protein could be practically useful bio-catalysts in the preparation of α-hydroxyketones including AC, HP, and R-PAC. To the best of our knowledge, this is the first time that bacterial AHAS was used as a catalyst to prepare HP with a good yield, and also the first time that TmcAHAS was employed to synthesize AC and R-PAC.
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49

Khemacheewakul, Julaluk, Siraphat Taesuwan, Rojarej Nunta, Charin Techapun, Yuthana Phimolsiripol, Pornchai Rachtanapun, Kittisak Jantanasakulwong et al. "Validation of mathematical model with phosphate activation effect by batch (R)-phenylacetylcarbinol biotransformation process utilizing Candida tropicalis pyruvate decarboxylase in phosphate buffer". Scientific Reports 11, n. 1 (3 giugno 2021). http://dx.doi.org/10.1038/s41598-021-91294-0.

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AbstractThe (R)-phenylacetylcarbinol (PAC) batch biotransformation kinetics for partially purified Candida tropicalis TISTR 5350 pyruvate decarboxylase (PDC) were determined to validate a comprehensive mathematical model in 250 mL scale with 250 mM phosphate buffer/pH 7.0. PDC could convert initial 100/120 mM benzaldehyde/pyruvate substrates to the statistical significantly highest (p ≤ 0.05) maximum PAC concentration (95.8 ± 0.1 mM) and production rate (0.639 ± 0.001 mM min−1). A parameter search strategy aimed at minimizing overall residual sum of square (RSST) based on a system of six ordinary differential equations was applied to PAC biotransformation profiles with initial benzaldehyde/pyruvate concentration of 100/120 and 30/36 mM. Ten important biotransformation kinetic parameters were then elucidated including the zeroth order activation rate constant due to phosphate buffer species (ka) of (9.38 ± < 0.01) × 10–6% relative PDC activity min−1 mM−1. The validation of this model to independent biotransformation kinetics with initial benzaldehyde/pyruvate concentration of 50/60 mM resulted in relatively good fitting with RSST, mean sum of square error (MSE), and coefficient of determination (R2) values of 662, 17.4, and 0.9863, respectively.
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