ChemInform Abstract: Bakers′ Yeast‐Mediated Transformations in Organic Chemistry

Abstract

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Yeast cell factories for fine chemical and API production

“…The first comprehensive overview of reduction reactions catalyzed by yeast was published in 1949 [ 33 ]. Since that time, many different substrates containing carbonyl moieties were subjected to yeast bioreduction and the most important achievements were summarized in reviews and book chapters, partly focusing on Saccharomyces cerevisiae [ 30 , 34 , 35 ] but also on biocatalysts in general, including alternative yeasts [ 24 , 25 , 36 - 43 ]. The investigated substrate spectrum is huge, including a variety of functional groups as substituents of the ketone moiety (for example heterocyclic-, hydroxyl-, sulfur-, cyano-, and azido-groups, or different halogenides) and even derivatives such as silyl- or germyl-groups were found to be accepted [ 24 ].…”

“…Generally, Saccharomyces cerevisiae reduces simple aliphatic and aromatic ketones according to Prelog's rule [ 44 ] resulting in the corresponding ( S )-alcohols [ 45 ] (Figure 1 ). However, this should not always be generalized and caution should be exercised in particular, when Prelog's rule is applied to whole cells [ 34 ].…”

“…However, first yeast-catalyzed deacylation reactions were regarded to be undesired side-reactions when Mamoli et al [ 94 ] was studying whole cells of baker's yeast for the stereoselective reduction of estrogen ester. Later, the whole variety of hydrolysis reactions performed by Saccharomyces cerevisiae was investigated and comprehensive reviews on the properties of proteinases [ 95 ], lipases and esterases [ 34 ] were given. What was encountered quite fast was the complex reaction control when whole microbial cells were employed [ 24 ].…”

“…From a synthetic point of view, carbon-carbon bond forming reactions are highly interesting as new asymmetric carbon centers can be formed. However, this type of yeast whole-cell biotransformation was and is limited to only a few examples [ 30 , 34 ]. The most prominent and industrially employed acyloin condensation performed by Saccharomyces cerevisiae yields in the formation of (1 R )-phenylacetyl carbinol, a chiral synthon of D-ephedrine (Table 2 and Additional File 2 ).…”

Conjugated Oligoelectrolytes: Materials for Acceleration of Whole Cell Biocatalysis

“…Figure 3a shows that L-malic acid production with nontreated yeast cells occurs in a manner consistent with literature precedent and that there is an increase in production with DSSN+. 34,35 After 21 h, the concentration of L-malic acid in the reaction treated with 100 μM DSSN+ is 3.6 times larger than that of the control. CTAB also increases L-malic acid production, as established previously.…”