Bagchi B (2013) The hydrophobic effect. In: Water in biological and chemical processes: from structure and dynamics to function. Cambridge University Press, 215–242

Bsharat O, Musa MM, Vieille C, Oladepo SA, Takahashi M, Hamdan SM (2017) Asymmetric reduction of substituted 2-tetralones by Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase. ChemCatChem 9:1487–1493. https://doi.org/10.1002/cctc.201601618

Article  CAS  Google Scholar 

Chen Q, Guo M, Bi Y, Qu G, Sun Z, Wang Y, Luo G (2021) Whole-cell biocatalytic synthesis of S -(4-chlorophenyl)-(pyridin-2-yl) methanol in a liquid–liquid biphasic microreaction system. Bioresour Technol 330:125022. https://doi.org/10.1016/j.biortech.2021.125022

Article  CAS  PubMed  Google Scholar 

Ensari Y, Dhoke GV, Davari MD, Ruff AJ, Schwaneberg U (2018) A comparative reengineering study of cpADH5 through iterative and simultaneous multisite saturation mutagenesis. ChemBioChem 19:1563–1569. https://doi.org/10.1002/cbic.201800159

Article  CAS  PubMed  Google Scholar 

Hall M (2021) Enzymatic strategies for asymmetric synthesis. RSC Chem Biol 2:958–989. https://doi.org/10.1039/d1cb00080b

Article  CAS  PubMed  PubMed Central  Google Scholar 

Hoshino T, Yamabe E, Hawari MA, Tamura M, Kanamaru S, Yoshida K, Koesoema AA, Matsuda T (2020) Oxidation of aromatic and aliphatic aldehydes to carboxylic acids by Geotrichum candidum aldehyde dehydrogenase. Tetrahedron 76:131387. https://doi.org/10.1016/j.tet.2020.131387

Article  CAS  Google Scholar 

Hou J, Xu G, Ni Y (2020) Stereochemistry in asymmetric reduction of bulky-bulky ketones by alcohol dehydrogenases. ACS Catal 10:10954–10966. https://doi.org/10.1021/acscatal.0c02646

Article  CAS  Google Scholar 

Jiang Y, Li X, Liu B, Tong F, Qu G, Sun Z (2022) Engineering the hydrogen transfer pathway of an alcohol dehydrogenase to increase activity by rational enzyme design. Mol Catal 530:112603. https://doi.org/10.1016/j.mcat.2022.112603

Article  CAS  Google Scholar 

Koesoema AA, Sugiyama Y, T.sriwong K, Xu Z, Verina S, Standley DM, Senda M, Senda T, Matsuda T (2019) Reversible control of enantioselectivity by the length of ketone substituent in biocatalytic reduction. Appl Microbiol Biotechnol 103:9529–9541. https://doi.org/10.1007/S00253-019-10206-5

Article  CAS  PubMed  Google Scholar 

Koesoema AA, Sugiyama Y, Xu Z, Standley DM, Senda M, Senda T, Matsuda T (2019) Structural basis for a highly (S)-enantioselective reductase towards aliphatic ketones with only one carbon difference between side chain. Appl Microbiol Biotechnol 103:9543–9553. https://doi.org/10.1007/s00253-019-10093-w

Article  CAS  PubMed  Google Scholar 

Koesoema AA, Standley DM, Ohshima S, Tamura M, Matsuda T (2020) Control of enantioselectivity in the enzymatic reduction of halogenated acetophenone analogs by substituent positions and sizes. Tetrahedron Lett 61:151820. https://doi.org/10.1016/j.tetlet.2020.151820

Article  CAS  Google Scholar 

Koesoema AA, Standley DM, Senda T, Matsuda T (2020) Impact and relevance of alcohol dehydrogenase enantioselectivities on biotechnological applications. Appl Microbiol Biotechnol 104:2897–2909. https://doi.org/10.1007/s00253-020-10440-2

Article  CAS  PubMed  Google Scholar 

Koesoema AA, Standley DM, T.sriwong K, Tamura M, Matsuda T (2020) Access to both enantiomers of substituted 2-tetralol analogs by a highly enantioselective reductase. Tetrahedron Lett 61:151682. https://doi.org/10.1016/j.tetlet.2020.151682

Article  CAS  Google Scholar 

Li D, Lou Y, Xu J, Chen X, Lin X, Wu Q (2021) Electronic effect-guided rational design of Candida antarctica lipase B for kinetic resolution towards diarylmethanols. Adv Synth Catal 363:1867–1872. https://doi.org/10.1002/adsc.202001367

Article  CAS  Google Scholar 

Liu X, Bastian S, Snow CD, Brustad EM, Saleski TE, Xu J, Meinhold P, Arnold FH (2012) Structure-guided engineering of Lactococcus lactis alcohol dehydrogenase LlAdhA for improved conversion of isobutyraldehyde to isobutanol. J Biotechnol 164:188–195. https://doi.org/10.1016/j.jbiotec.2012.08.008

Article  CAS  PubMed  PubMed Central  Google Scholar 

Liu B, Qu G, Li J, Fan W, Ma J, Xu Y, Nie Y, Sun Z (2019) Conformational dynamics-guided loop engineering of an alcohol dehydrogenase: capture, turnover and enantioselective transformation of difficult-to-reduce ketones. Adv Synth Catal 361:3182–3190. https://doi.org/10.1002/adsc.201900249

Article  CAS  Google Scholar 

Liu J, Li W, Li Y, Liu Y, Ke Z (2021) Selective C-alkylationbetween alcohols catalyzed by N-heterocyclic carbene molybdenum. Chem - An Asian J 16:3124–3128. https://doi.org/10.1002/asia.202100959

Article  CAS  Google Scholar 

Maurer D, Enugala TR, Hamnevik E, Bauer P, Lüking M, Petrović D, Hillier H, Kamerlin SCL, Dobritzsch D, Widersten M (2018) Stereo- and regioselectivity in catalyzed transformation of a 1,2-disubstituted vicinal diol and the corresponding diketone by wild type and laboratory evolved alcohol dehydrogenases. ACS Catal 8:7526–7538. https://doi.org/10.1021/acscatal.8b01762

Article  CAS  Google Scholar 

Mozhaev VV, Berezin IV, Martinek K (1988) Structure-stability relationship in proteins: fundamental tasks and strategy for the development of stabilized enzyme catalysts for biotechnology. Crit Rev Biochem Mol Biol 23:235–281. https://doi.org/10.3109/10409238809088225

Article  CAS  Google Scholar 

Musa MM, Ziegelmann-Fjeld KI, Vieille C, Zeikus JG, Phillips RS (2007) Asymmetric reduction and oxidation of aromatic ketones and alcohols using W110A secondary alcohol dehydrogenase from Thermoanaerobacter ethanolicus. J Org Chem 72:30–34. https://doi.org/10.1021/jo0616097

Article  CAS  PubMed  Google Scholar 

Nakamura K, Inoue Y, Matsuda T, Misawa I (1999) Stereoselective oxidation and reduction by immobilized Geotrichum candidum in an organic solvent. J Chem Soc - Perkin Trans 1:2397–2402. https://doi.org/10.1039/a900936a

Article  Google Scholar 

Nakata Y, Fukae T, Kanamori R, Kanamaru S, Matsuda T (2010) Purification and characterization of acetophenone reductase with excellent enantioselectivity from Geotrichum candidum NBRC 4597. Appl Microbiol Biotechnol 86:625–631. https://doi.org/10.1007/S00253-009-2329-5

Article  CAS  PubMed  Google Scholar 

Nian S, Ling F, Chen J, Wang Z, Shen H, Yi X, Yang Y, She Y, Zhong W (2019) Highly enantioselective hydrogenation of non-ortho-substituted 2-pyridyl aryl ketones via iridium-f-diaphos catalysis. Org Lett 21:5392–5396. https://doi.org/10.1021/acs.orglett.9b01415

Article  CAS  PubMed  Google Scholar 

Otsu M, Suzuki Y, Koesoema AA, Hoang HN, Tamura M, Matsuda T (2020) CO2-expanded liquids as solvents to enhance activity of Pseudozyma antarctica lipase B towards ortho-substituted 1-phenylethanols. Tetrahedron Lett 61:152424. https://doi.org/10.1016/j.tetlet.2020.152424

Article  CAS  Google Scholar 

Özdemir A, Şahin E (2024) A multi-response nonlinear programming model with an inscribed design to optimize bioreduction conditions of (S)-phenyl(pyridin-2-yl)methanol by Leuconostoc pseudomesenteroides N13. Arab J Sci Eng 49:8225–8235. https://doi.org/10.1007/s13369-024-08773-5

Article  CAS  Google Scholar 

Prelog V (1964) Specification of the stereospecificity of some oxido-reductases by diamond lattice sections. Pure Appl Chem 9:119–130. https://doi.org/10.1351/pac196409010119

Article  CAS  Google Scholar 

Qin F, Qin B, Zhang W, Liu Y, Su X, Zhu T, Ouyang J, Guo J, Li Y, Zhang F, Tang J, Jia X, You S (2018) Discovery of a switch between Prelog and anti-Prelog reduction toward halogen-substituted acetophenones in short-chain dehydrogenase/reductases. ACS Catal 8:6012–6020. https://doi.org/10.1021/acscatal.8b00807

Article  CAS  Google Scholar 

Qu G, Bi Y, Liu B, Li J, Han X, Liu W, Jiang Y, Qin Z, Sun Z (2022) Unlocking the stereoselectivity and substrate acceptance of enzymes: proline-induced loop engineering test. Angew Chemie - Int Ed 61:e202110793. https://doi.org/10.1002/anie.202110793

Article  CAS  Google Scholar 

Qu G, Liu B, Jiang Y, Nie Y, Yu H, Sun Z (2019) Laboratory evolution of an alcohol dehydrogenase towards enantioselective reduction of difficult-to-reduce ketones. Bioresour Bioprocess 6:18. https://doi.org/10.1186/s40643-019-0253-9

Article  Google Scholar 

Sardauna AE, Abdulrasheed M, Nzila A, Musa MM (2023) Biocatalytic asymmetric reduction of prochiral bulky-bulky ketones. Mol Catal 541:113099. https://doi.org/10.1016/j.mcat.2023.113099

Article  CAS  Google Scholar 

Shanbhag AP (2023) Stairway to stereoisomers: engineering short- and medium-chain ketoreductases to produce chiral alcohols. ChemBioChem 24:e202200687. https://doi.org/10.1002/cbic.202200687