Microbially-aided preparation of (S)-2-Methoxycyclohexanone key intermediate in the synthesis of Sanfetrinem

Quantum mechanical calculations of the cephalosporin nucleus

“…As the number of bacterial strains acquiring resistance to the current antibiotic drugs grows, efforts are devoted to the development and the discovery of new antibiotics capable of overcoming such resistance. Those efforts focus on the quantitative structure activity analysis of these antibiotics [3][4][5][6][7][8][9][10][11][12], their biosynthesis [13] and the mechanism of the alkaline hydrolysis of b-lactam antibiotics [2c,14]. However, for developing and designing a new series of penicillins and cephalosporins, deep knowledge of the b-lactam, the thiazolidine and the dihydrothiazine rings is essential.…”

Yarrowia lipolytica Yeast: A Treasure Trove of Enzymes for Biocatalytic Applications—A Review

“…Furthermore, such a method is particularly advantageous in terms of cost-effectiveness, ease of preparation, and the ability to effectively perform several types of reactions [14]. Table 1 demonstrates the past application of whole cells of Y. lipolytica as a biocatalyst in various reactions, including hydrogenation, reduction, and oxidation [15][16][17][18][19][20][21][22][23][24][25][26][27][28][29].…”

“…The first mention of the use of Y. lipolytica yeast in bioreduction reactions and obtaining optically active alcohols appeared in 1997. Fuganti et al [17] discussed the preparation of (S)-2-methoxycyclohexanone, a crucial intermediate in the synthesis of the antibiotic sanfetrinem. Interestingly, as the authors claimed, the most extraordinary result was achieved when Y. lipolytica was used, which, unlike other yeast species, allowed obtaining R enantiomer of 2-benzylidenecyclohexanol from 2-benzylidenecyclohexanone with a yield of 40% after 24 h and the enantiomeric excess (ee) of 93%.…”

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“…Choice of organism can allow the selective reduction of the C᎐ ᎐ O alone or saturative reduction in certain stereoselective α,β-unsaturated ketone reductions. 330 Similarly, the use of Pichia farinosa-catalyzed reduction followed by PCC oxidation allows the overall preparation of cyclohexanones from α,β-unsaturated counterparts with fair to good stereoselectivity. 331 The apparent baker's yeast-catalyzed stereoselective reduction of the C᎐ ᎐ C double bond of an allylic alcohol probably proceeded via the enal.…”