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Enzyme-Catalyzed Asymmetric Domino Thia-Michael/Aldol Condensation Using Pepsin

Yang Xiang, Jian Song, Yong Zhang, Da-Cheng Yang, Zhi Guan, Yan-Hong He

J Org Chem. 2016 Jul 15;81(14):6042-8.

PMID: 27348476

Abstract:

The novel catalytic promiscuity of pepsin from porcine gastric mucosa for the asymmetric catalysis of the domino thia-Michael/aldol condensation reaction in MeCN and buffer was discovered for the first time. Broad substrate specificity was tested, and a series of corresponding products were obtained with enantioselectivities of up to 84% ee. This specific catalysis was demonstrated by using recombinant pepsin and control experiments with denatured and inhibited pepsin. The reaction was also shown to occur in the active site by site-directed mutagenesis (the Asp32Ala mutant of pepsin), and a possible mechanism was proposed.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP9001756 Pepsin from porcine gastric mucosa Pepsin from porcine gastric mucosa 9001-75-6 Price
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