Production of enantiomerically enriched chiral carbinols using Weissella paramesenteroides as a novel whole cell biocatalyst

References

• Carlsen PHJ, Katsuki T, Martin VS, Sharpless KB. 1981. A greatly improved procedure for ruthenium tetroxide catalyzed oxidations of organic compounds. J Org Chem. 46:3936–3938.
   Web of Science ®Google Scholar
• Comasseto JV, Andrade LH, Omori AT, Assis LF, Porto ALM. 2004. Deracernization of aryl ethanols and reduction of acetophenones by whole fungal cells of Aspergillus terreus CCT 4083, A. terreus CCT 3320 and Rhizopus oryzae CCT 4964. J Mol Catal B Enzym. 29:55–61.
   Google Scholar
• Contente ML, Serra I, Palazzolo L, Parravicini C, Gianazza E, Eberini I, Pinto A, Guidi B, Molinari F, Romano D. 2016. Enzymatic reduction of acetophenone derivatives with a benzil reductase from Pichia glucozyma (KRED1-Pglu): electronic and steric effects on activity and enantioselectivity. Org Biomol Chem. 14:3404–3408.
   PubMed Web of Science ®Google Scholar
• Corey EJ, Helal CJ. 1996. Catalytic enantioselective synthesis of the second generation histamine antagonist cetirizine hydrochloride. Tetrahedron Lett. 37:4837–4840.
   Web of Science ®Google Scholar
• Cui YH, Wei P, Peng F, Zong MH, Lou WY. 2018. Efficient biocatalytic stereoselective reduction of methyl acetoacetate catalyzed by whole cells of engineered E. coli. RSC Adv. 8:9970–9978.
   Web of Science ®Google Scholar
• Dertli E, Mercan E, Arıcı M, Yılmaz MT, Sağdıç O. 2016. Characterisation of lactic acid bacteria from Turkish sourdough and determination of their exopolysaccharide (EPS) production characteristics. LWT Food Sci Technol. 71:116–124.
   Web of Science ®Google Scholar
• Devalia JL, De Vos C, Hanotte F, Baltes E. 2001. A randomized, double‐blind, crossover comparison among cetirizine, levocetirizine, and ucb 28557 on histamine‐induced cutaneous responses in healthy adult volunteers. Allergy. 56:50–57.
   PubMed Web of Science ®Google Scholar
• Devaux-Basseguy R, Bergel A, Comtat M. 1997. Potential applications of NAD (P)-dependent oxidoreductases in synthesis: a survey. Enzyme Microb Technol. 20:248–258.
   Web of Science ®Google Scholar
• Di Nunno L, Franchini C, Nacci A, Scilimati A, Sinicropi MS. 1999. Baker's yeast-induced asymmetric reduction of a-ketosulfides: synthesis of optically active 1-(benzothiazol-2-ylsulfanyl)-2-alkanols, 2-alkanols, and thiiranes. Tetrahedron: Asymmetry. 10:1913–1926.
   Web of Science ®Google Scholar
• Dudzik A, Snoch W, Borowiecki P, Opalinska-Piskorz J, Witko M, Heider J, Szaleniec M. 2015. Asymmetric reduction of ketones and β-keto esters by (S)-1-phenylethanol dehydrogenase from denitrifying bacterium Aromatoleum aromaticum. Appl Microbiol Biotechnol. 99:5055–5069.
   PubMed Web of Science ®Google Scholar
• Gao K, Song Q, Wei D. 2006. Coupling of enantioselective biooxidation of DL-1,2-propanediol and bioreduction of pinacolone via regeneration cycle of coenzyme. Appl Microbiol Biotechnol. 71:819–823.
   PubMed Web of Science ®Google Scholar
• Garzón-Posse F, Becerra-Figueroa L, Hernández-Arias J, Gamba-Sánchez D. 2018. Whole cells as biocatalysts in organic transformations. Molecules. 23:1265.
   Web of Science ®Google Scholar
• Guo J, Chen J, Lu Z. 2015. Cobalt-catalyzed asymmetric hydroboration of aryl ketones with pinacolborane. Chem Commun (Camb). 51:5725–5727.
   PubMed Web of Science ®Google Scholar
• Hage A, Petra DGI, Field JA, Schipper D, Wijnberg JBPA, Kamer PCJ, Reek JNH, van Leeuwen PWNM, Wever R, Schoemaker HE. 2001. Asymmetric reduction of ketones via whole cell bioconversions and transfer hydrogenation: complementary approaches. Tetrahedron: Asymmetry. 12:1025–1034.
   Web of Science ®Google Scholar
• Houng JY, Liau JS. 2006. Mathematical modeling of asymmetric reduction of ethyl 4-chloro acetoacetate by bakers'yeast. Enzyme Microb Technol. 38:879–886.
   Web of Science ®Google Scholar
• Liang P, Qin B, Mu M, Zhang X, Jia X, You S. 2013. Prelog and anti-Prelog stereoselectivity of two ketoreductases from Candida glabrata. Biotechnol Lett. 35:1469–1473.
   PubMed Web of Science ®Google Scholar
• Lin H, Chen YZ, Xu XY, Xia SW, Wang LX. 2009. Preparation of key intermediates of adrenergic receptor agonists: highly enantioselective production of (R)-α-halohydrins with Saccharomyces cerevisiae CGMCC 2.396. J Mol Catal B Enzym. 57:1–5.
   Google Scholar
• Mandal D, Ahmad A, Khan MI, Kumar RJ. 2004. Enantioselective bioreduction of acetophenone and its analogous by the fungus Trichothecium sp. J Mol Catal B: Enzym. 27:61–63.
   Web of Science ®Google Scholar
• Meguro K, Aizawa M, Sohda T, Kawamatsu Y, Nagaoka A. 1985. New 1, 4-dihydropyridine derivatives with potent and long-lasting hypotensive effect. Chem Pharm Bull. 33:3787–3797.
   PubMed Web of Science ®Google Scholar
• Murzin DY, Maki-Arvela P, Toukoniitty E, Salmi T. 2005. Asymmetric heterogeneous catalysis: science and engineering. Catal Rev. 47:175–256.
   Web of Science ®Google Scholar
• Musa MM, Bsharat O, Karume I, Vieille C, Takahashi M, Hamdan SM. 2018. Expanding the substrate specificity of Thermoanaerobacter pseudoethanolicus secondary alcohol dehydrogenase by a dual site mutation. Eur J Org Chem. 2018:798–805.
   Web of Science ®Google Scholar
• Öksüz S, Şahin E, Dertli E. 2018. Synthesis of enantiomerically enriched drug precursors by Lactobacillus paracasei BD87E6 as a biocatalyst. Chem Biodivers. 15:e1800028.
   PubMed Web of Science ®Google Scholar
• Pereira RS. 1998. The use of baker’s yeast in the generation of asymmetric centers to produce chiral drugs and other compounds. Crit Rev Biotechnol. 18:25–64.
   PubMed Web of Science ®Google Scholar
• Pérez HI, Luna H, Manjarrez N, Solís A. 2001. Microbiological resolution of chiral arylethyl carbinols by Nocardia corallina. Biotechnol Lett. 23:1467–1472.
   Web of Science ®Google Scholar
• Perrone MG, Santandrea E, Bleve L, Vitale P, Colabufo NA, Jockers R, Milazzo FM, Sciarroni AF, Scilimati A. 2008. Stereospecific synthesis and bio-activity of novel beta(3)-adrenoceptor agonists and inverse agonists. Bioorg Med Chem. 16:2473–2488.
   PubMed Web of Science ®Google Scholar
• Perrone MG, Santandrea E, Scilimati A, Syldatk C, Tortorella V. 2005. Screening yeasts for the stereoselective reduction of oxoester clofibrate analogues. Tetrahedron: Asymmetry. 16:1473–1477.
   Web of Science ®Google Scholar
• Pollard DJ, Woodley JM. 2007. Biocatalysis for pharmaceutical intermediates: the future is now. Trends Biotechnol. 25:66–73.
   PubMed Web of Science ®Google Scholar
• Ramacciotti A, Fiaschi R, Napolitano E. 1996. Enantioselective synthesis of natural combretastatin. Tetrahedron: Asymmetry. 7:1101–1104.
   Web of Science ®Google Scholar
• Rodríguez C, Borzęcka W, Sattler JH, Kroutil W, Lavandera I, Gotor V. 2014. Steric vs. electronic effects in the Lactobacillus brevis ADH-catalyzed bioreduction of ketones. Org Biomol Chem. 12:673–681.
   PubMed Web of Science ®Google Scholar
• Şahin E. 2017. Debaryomyces hansenii as a new biocatalyst in the asymmetric reduction of substituted acetophenones. Biocatal Biotransformation. 35:363–371.
   Web of Science ®Google Scholar
• Şahin E. 2018. Production of (R)-1-(1,3-benzodioxol-5-yl)ethanol in high enantiomeric purity by Lactobacillus paracasei BD101. Chirality. 30:189–194.
   PubMed Web of Science ®Google Scholar
• Şahin E, Dertli E. 2017. Highly enantioselective production of chiral secondary alcohols with Candida zeylanoides as a new whole cell biocatalyst. Chem Biodivers. 14:e1700121.
   Web of Science ®Google Scholar
• Salvi NA, Chattopadhyay S. 2016. Laboratory scale-up synthesis of chiral carbinols using Rhizopus arrhizus. Tetrahedron: Asymmetry. 27:188–192.
   Google Scholar
• Schmidt F, Stemmler RT, Rudolph J, Bolm C. 2006. Catalytic asymmetric approaches towards enantiomerically enriched diarylmethanols and diarylmethylamines. Chem Soc Rev. 35:454–470.
   PubMed Web of Science ®Google Scholar
• Siedler S, Lindner SN, Bringer S, Wendisch VF, Bott M. 2013. Reductive whole-cell biotransformation with Corynebacterium glutamicum: improvement of NADPH generation from glucose by a cyclized pentose phosphate pathway using pfkA and gapA deletion mutants. Appl Microbiol Biotechnol. 97:143–152.
   PubMed Web of Science ®Google Scholar
• Timpson LM, Liliensiek A-K, Alsafadi D, Cassidy J, Sharkey MA, Liddell S, Allers T, Paradisi F. 2013. A comparison of two novel alcohol dehydrogenase enzymes (ADH1 and ADH2) from the extreme halophile Haloferax volcanii. Appl Microbiol Biotechnol. 97:195–203.
   PubMed Web of Science ®Google Scholar
• Viatcheslav S, Melvin DJ, Wildeliz C, Lorianne B, Cindybeth V, Irisbel G, Margarita OM. 2009. Chiral spiroaminoborate ester as a highly enantioselective and efficient catalyst for the borane reduction of furyl, thiophene, chroman and thiochroman containing ketones. Tetrahedron: Asymmetry 20:2659–2665.
   PubMed Web of Science ®Google Scholar
• Vitale P, D’Introno C, Perna FM, Perrone MG, Scilimati A. 2013. Kluyveromyces marxianus CBS 6556 growing cells as a new biocatalyst in the asymmetric reduction of substituted acetophenones. Tetrahedron: Asymmetry. 24:389–394.
   Web of Science ®Google Scholar
• Vitale P, Perna FM, Agrimi G, Pisano I, Mirizzi F, Capobianco RV, Capriati V. 2018. Whole-cell biocatalyst for chemoenzymatic total synthesis of rivastigmine. Catalysts. 8:55.
   Web of Science ®Google Scholar
• Vitale P, Perna FM, Perrone MG, Scilimati A. 2011. Screening on the use of Kluyveromyces marxianus CBS 6556 growing cells as enantioselective biocatalysts for ketone reductions. Tetrahedron: Asymmetry. 22:1985–1993.
   Web of Science ®Google Scholar
• Wang P, Liu Y, Zhang YL, Da CS. 2017. The inexpensive additive N-methylmorpholine effectively decreases the equivalents of nucleophiles in the catalytic highly enantioselective arylation of aryl aldehydes. Chirality. 29:443–450.
   PubMed Web of Science ®Google Scholar
• Wang X, Zhang J, Liu Y, Cui Y. 2014. Chiral porous TADDOL-embedded organic polymers for asymmetric diethylzinc addition to aldehydes. BCSJ. 87:435–440.
   Google Scholar
• Wu W, Liu S, Duan M, Tan X, Chen C, Xie Y, Lan Y, Dong X-Q, Zhang X. 2016. Iridium catalysts with f-amphox ligands: asymmetric hydrogenation of simple ketones. Org Lett. 18:2938–2941.
   PubMed Web of Science ®Google Scholar
• Yılmaz D, Şahin E, Dertli E. 2017. Highly enantioselective production of chiral secondary alcohols using Lactobacillus paracasei BD 101 as a new whole cell biocatalyst and evaluation of their antimicrobial effects. Chem Biodivers. 14:e1700269.
   Web of Science ®Google Scholar
• Zhong J, Guo H, Wang M, Yin M, Wang M. 2007. Asymmetric diethylzinc addition and phenyl transfer to aldehydes using chiral cis-cyclopropane-based amino alcohols. Tetrahedron: Asymmetry. 18:734–741.
   Google Scholar
• Zilbeyaz K, Taskın M, Kurbanoglu EB, Kurbanoglu NI, Kilic H. 2010. Production of (R)-1-phenylethanols through bioreduction of acetophenones by a new fungus isolate Trichothecium roseum. Chirality. 22:543–547.
   PubMed Web of Science ®Google Scholar