[Research progress of Pictet-Spenglerases]

Sheng Wu Gong Cheng Xue Bao. 2020 Oct 25;36(10):2001-2016. doi: 10.13345/j.cjb.200064.
[Article in Chinese]

Abstract

Pictet-Spenglerases (P-Sases) catalyze the Pictet-Spengler (P-S) reactions and exhibit high stereoselectivity and regioselectivity under mild conditions. The typical P-S reaction refers to the condensation and recyclization of β-arylethylamine with aldehyde or ketone under acidic conditions to form tetrahydroisoquinoline and β-carboline alkaloid derivatives. The related enzymatic products of P-Sases are the backbones of various bioactive compounds, including clinical drugs: morphine, noscapine, quinine, berberine, ajmaline, morphine. Furthermore, the activity of P-Sases in stereoselective and regioselective catalysis is also valuable for chemoenzymatic synthesis. Therefore, this review summarizes the research progress in the discovery, functional identification, biological characteristics and catalytic applications of P-Sases, which provide the useful theoretical reference in future P-Sases research and development.

Pictet-Spengler (P-S) 反应通常是指-芳基乙胺在酸性条件下与醛或者酮发生缩合后环化形成四氢异喹啉或β-咔啉类生物碱结构的一类化学反应。而催化这类高度立体选择性和区域选择性反应的酶称为Pictet-Spenglerase (P-S 酶)。P-S 酶是一类重要的活性产物生物合成催化酶,广泛分布于吗啡、那可丁、奎宁、小檗碱、阿吗灵等临床药物以及一些先导化合物的生物合成途径中,应用开发前景广阔。鉴于此,文中对P-S 酶的发现、功能鉴定、生物学特性以及催化应用等方面的研究进展进行了归纳总结,以期为P-S 酶的后续发掘及系统研究提供良好的借鉴和参考。.

Keywords: Pictet-Spengler reaction; Pictet-Spenglerase; alkaloid; biocatalysis; biosynthesis.

Publication types

  • Review

MeSH terms

  • Alkaloids* / chemistry
  • Catalysis
  • Enzymes* / metabolism
  • Research* / trends
  • Tetrahydroisoquinolines* / chemistry

Substances

  • Alkaloids
  • Enzymes
  • Tetrahydroisoquinolines
  • 1,2,3,4-tetrahydroisoquinoline