Asymmetric Morita–Baylis–Hillman reaction catalyzed by pepsin

Pepsin from porcine gastric mucous shown catalytic promiscuity was first used to catalyze Morita–Baylis–Hillman reaction in combination with 1,4-diazabicyclo[2.2.2]octane (DABCO). [Display omitted] •Pepsin-catalyzed Morita–Baylis–Hillman (MBH) reaction was described.•15 examples of MBH products were...

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Bibliographic Details
Published in:Journal of molecular catalysis. B, Enzymatic Enzymatic, 2016-02, Vol.124, p.62-69
Main Authors: Xue, Jing-Wen, Song, Jian, Manion, Ian C.K., He, Yan-Hong, Guan, Zhi
Format: Article
Language:English
Subjects:
Asymmetric MBH reaction
Biocatalyst
Enzyme catalytic promiscuity
Porcine pepsin
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Summary:Pepsin from porcine gastric mucous shown catalytic promiscuity was first used to catalyze Morita–Baylis–Hillman reaction in combination with 1,4-diazabicyclo[2.2.2]octane (DABCO). [Display omitted] •Pepsin-catalyzed Morita–Baylis–Hillman (MBH) reaction was described.•15 examples of MBH products were obtained by this reaction.•The novel reaction also expands the field of organic synthesis.•This work promotes the development of enzyme catalytic promiscuity. Pepsin from porcine gastric mucous shown catalytic promiscuity was first discovered to catalyze the Morita–Baylis–Hillman (MBH) reaction between aromatic aldehydes with 2-cyclohexen-1-one or 2-cyclopenten-1-one in a two-phase medium of phosphate buffer/cyclohexane in the presence of 1,4-diazabicyclo[2.2.2]octane (DABCO). The best results of the corresponding MBH products up to 77% yield and 38% ee were achieved.
ISSN:1381-1177
1873-3158
DOI:10.1016/j.molcatb.2015.12.002