3- Oxo-4-phenyl-p-lactam

A recombinant Escherichia coli strain overexpressing yeast reductase Ara Ip was utilized for the reduction of racemic 3-oxo-4-phenyl-P-lactam 16 to cis-(3S,4R)-3-hydroxy-4-phenyl-p-lactam 17 [20]. Detailed studies in this case showed that only under mild optimized fermentation conditions, a DKR occurred in situ and a single enantiopure product was formed, as shown in Scheme 12.8. This reaction could also be carried out in gram scale. When the reaction was carried out in a shaking flask, the DKR was not effective and the yields of alcohols were low because of the starting material decomposition. No DKR was achieved in the case of substrates having 2-thiophenyl or 2-furyl substituents instead of the phenyl group. 

Yang Y, Drolet M, Kayser MM. The dynamic kinetic resolution of 3-oxo-4-phenyl-p-lactam by recombinant E. coli overexpressing yeast reductase Aralp. Tetrahedron Asymmetry 2005 16 2748-2753. 

Fig. 12 (a) Chemical structures of the fluorescent tracers synthesized for P-lactam antibiotic analysis PAAP [25,5/f, 6/ ]-3,3-dimethyl-7-oxo-6-[(pyren-l-ylacetyl) amino -4-thia-l-azabicyclo 3.2.0 heptane-2-carboxylic acid PBAP [2S,5/ ,6/J]-3,3-dimethyl-7-oxo-6-[(4-pyren-lylbutanoyl]amino]-4-thia-l-azabicyclo[3.2.0] heptane-2-carboxylic acid PAAM [2S,5/ ,6/ ]-3,3-dimethyl-7-oxo-6-( (2/f)-2-phenyl-2-[(pyren-l-ylacetyl)amino]ethanoyl amino)-4-thia-l-azabicyclo[3.2.0] heptane-2-carboxylic acid PBAM [2S,5/f,6/f]-3,3-dimethyl-7-oxo-6-( (2/f)-2-phenyl-2-[(pyren-l-ylbutanoyl)amino]ethanoyl ainino) l-thia-l-azabicyclo... 

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