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Chymopapain-Catalyzed Direct Asymmetric Aldol Reaction

Authors

  • Yan-Hong He,

    1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
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    • Yan-Hong He and Hai-Hong Li contributed equally to this work

  • Hai-Hong Li,

    1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
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    • Yan-Hong He and Hai-Hong Li contributed equally to this work

  • Yan-Li Chen,

    1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
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  • Yang Xue,

    1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
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  • Yi Yuan,

    1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
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  • Zhi Guan

    Corresponding author
    1. School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
    • School of Chemistry and Chemical Engineering, Southwest University, Chongqing 400715, People's Republic of China, Fax: (+86)-23-6825-4091
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Abstract

Chymopapain, a cysteine proteinase isolated from the latex of the unripe fruits of Carica papaya, displays a promiscuous activity to catalyze the direct asymmetric aldol reactions of aromatic and heteroaromatic aldehydes with cyclic and acyclic ketones in acetonitrile in the presence of a phosphate buffer. The excellent enantioselectivities of up to 96% ee and high diastereoselectivities of up to >99:1 (anti/syn) were achieved. The novel catalytic promiscuity of chymopapain widens the applicability of this biocatalyst in organic synthesis.

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