Enzymatic enantioselective aldol reactions of isatin derivatives with cyclic ketones under solvent-free conditions.
Nuclease p1 from Penicillium citrinum was observed to directly catalyze the asymmetric aldol reactions between isatin derivatives and cyclic ketones with high isolated yields (up to 95%) and moderate to good stereoselectivity (dr up to >99/1, ee up to 82%). A series of reaction conditions were investigated in detail, and the addition of deionized water had a big influence upon the enzyme activity. This case of biocatalytic promiscuity not only widens the applicability of nuclease p1 to new chemical transformation in organic synthesis, but also provides a potentially valuable method to construct pharmaceutically active compounds in medicinal chemistry.
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
Zhi-Qiang
ZQ
Liu
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
Zi-Wei
ZW
Xiang
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China.
Zhou
Z
Shen
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China. Electronic address: llc123@zju.edu.cn.
Qi
Q
Wu
Department of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China. Electronic address: llc123@zju.edu.cn.
Xian-Fu
XF
Lin
D000447:Aldehydes / Q000737:chemistry; D055162:Biocatalysis; D005656:Fungal Proteins / Q000737:chemistry*; D055772:Green Chemistry Technology; D007510:Isatin / Q000031:analogs & derivatives* / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D007700:Kinetics; D015719:Single-Strand Specific DNA and RNA Endonucleases / Q000737:chemistry*; D012997:Solvents / Q000737:chemistry; D013237:Stereoisomerism; D014867:Water / Q000737:chemistry
D000447:Aldehydes; D005656:Fungal Proteins; D007659:Ketones; D012997:Solvents; D014867:Water; D007510:Isatin; C526100:Nuclease P1, Penicillium citrinum; D015719:Single-Strand Specific DNA and RNA Endonucleases
3-Substituted-3-hydroxyindolin-2-ones; Asymmetric aldol reaction; Biocatalysis; Promiscuity; Solvent free