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Current Organocatalysis

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ISSN (Print): 2213-3372
ISSN (Online): 2213-3380

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Review Article

Baker’s Yeast-Based Organocatalysis: Applications in Organic Synthesis

Author(s): Biswa Mohan Sahoo* and Bimal Krishna Banik

Volume 6, Issue 2, 2019

Page: [158 - 164] Pages: 7

DOI: 10.2174/2213337206666181211105304

Abstract

Background: Catalyst speeds up any chemical reaction without changing the point of the equilibrium. Catalysis process plays a key role in organic synthesis to produce new organic compounds. Similarly, organocatalysis is a type of chemical catalysis in which the rate of a reaction is accelerated by organic catalysts.

Methods: Organocatalysts have gained significant utility in organic reactions due to their less of sensitivity towards moisture, readily available, economic, large chiral pool and low toxicity as compared to metal catalysts. Organocatalysts work via both formations of covalent bonds such as enamine and iminium catalysis as well as through non-covalent interactions such as in hydrogen bonding. For example, Bakers’ yeast based organocatalysis is widely used in various organic transformations.

Results: Baker’s yeast is a fermentation product and used mainly in the preparation of bread dough. It is produced by aerobic fermentation of yeast strain Saccharomyces cerevisiae. Baker's yeast consists of enzymes which can reduce a carbonyl group into a hydroxyl group with high yield and thereby making it suitable for biotransformations in organic synthesis.

Conclusion: Baker's yeast is widely used as a biocatalyst in various organic reactions such as oxidation, reduction, condensation, hydrolysis, cyclization, etc. because it is readily available, inexpensive and easy to handle.

Keywords: Baker's yeast, biotransformations, fermentation, hydrolysis, organocatalysis, synthesis.

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[1]
Cornils, B.; Herrmann, W.A. Applied homogeneous catalysis with organometallic compounds; Wiley-VCH: Weinheim, 2002.
[2]
Medson, C.; Smallridge, A.J.; Trewhella, M.A. Baker’s yeast activity in an organic solvent system. J. Mol. Catal., B Enzym., 2001, 11, 897-903.
[3]
Servi, S. Baker’s yeast as a reagent in organic synthesis. Synthesis, 1990, 1, 1-25.
[4]
Goswami, A.; Stewart, J. Organic synthesis using biocatalysis; Elsevier, 2015, pp. 1st ed. 345-438.
[5]
Saranraj, P.; Sivasakthivelan, P.; Suganthi, K. Baker’s Yeast: Historical development, genetic characteristics, biochemistry, fermentation and downstream processing. J. Acad. Ind. Res., 2017, 6(7), 111-119.
[6]
Csuk, R.; Glaenzer, B.I. Baker’s yeast mediated transformations in organic chemistry. Chem. Rev., 1991, 91, 49-97.
[7]
Saha, M.; Pal, A.K. Fermented baker’s yeast: An efficient catalyst for the synthesis of Pyran derivatives in water at room temperature. Synth. Commun., 2013, 43, 1708-1713.
[8]
Wolfson, A.; Haddad, N.; Dlugy, C.; Tavor, D. Baker’s yeast catalyzed asymmetric reduction of methyl acetoacetate in glycerol containing systems. Org. Commun, 2008, 1(2), 9-16.
[9]
Wolfson, A.; Dlugy, C.; Tavor, D. Baker’s yeast catalyzed asymmetric reduction of prochiral ketones in different reaction mediums. Org. Commun, 2013, 6(1), 1-11.
[10]
Rotthaus, O.; Krüger, D.; Demuth, M.; Schaffner, K. Reductions of keto esters with baker’s yeast in organic solvents: A comparison with the results in water. Tetrahedron, 1997, 53, 935-938.
[11]
Fronza, G.; Fuganti, C.; Grasselli, P.; Mele, A. On the mode of Baker’s yeast transformation of 3-chloropropiophenone and related ketones. Synthesis of (2S)-[2-2H] propiophenone, (R)-fluoxetine, and (R)- and (S)- fenfluramine. J. Org. Chem., 1991, 56, 6019-6023.
[12]
Florjańczyk, E.B.; Kapturowska, A.U. Genetically modified baker’s yeast saccharomyces cerevisiae in chemical synthesis and biotransformations; Chem. Bio, 2012, pp. 211-234.
[13]
Singh, N.G.; Nongrum, R.; Jims, C.K. Bakers’ yeast: an environment benign catalyst for the one-pot synthesis of indolyl chromenes and bisindolyl alkanes. Green Chem. Lett. Rev., 2014, 7(2), 137-144.
[14]
Silva, V.D.; Carletto, J.S.; Nascimento, M.D. Asymmetric reduction of (4S)-(+)-carvone catalyzed by baker’s yeast: A green method for monitoring the conversion based on liquid-liquid-liquid microextraction with polypropylene hollow fiber membranes. Process Biochem., 2013, 48(8), 1159-1165.
[15]
Bujons, J.; Guajardo, R.; and Kyler, K.S. Enantioselective enzymatic sterol synthesis by ultrasonically stimulated Baker’s yeast. J. Am. Chem. Soc., 1988, 110, 604-606.
[16]
Pereira, R.S. The use of Baker’s Yeast in the generation of asymmetric centers to produce chiral drugs and other compounds. Crit. Rev. Biotechnol., 1998, 18(1), 25-64.
[17]
Brown, R.F.; Jackson, W.R.; McCarthy, T.D. A synthesis of (-)-Denopamine. Tetrahedron Asym, 1993, 4, 2149-2150.

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