17459-85-7Relevant articles and documents
Synthesis, Purification, and Selective β2-AR Agonist and Bronchodilatory Effects of Catecholic Tetrahydroisoquinolines from Portulaca oleracea
Yang, Er-Lan,Sun, Bin,Huang, Zi-Yi,Lin, Jian-Guang,Jiao, Bo,Xiang, Lan
, p. 2986 - 2993 (2019/11/03)
A green, biomimetic, phosphate-mediated Pictet-Spengler reaction was used in the synthesis of three catecholic tetrahydroisoquinolines, 1, 2, and 12, present in the medicinal plant Portulaca oleracea, as well as their analogues 3-11, 13, and 14, with dopa
Asymmetric synthesis of tetrahydroisoquinolines by enzymatic Pictet-Spengler reaction
Nishihachijo, Masakatsu,Hirai, Yoshinori,Kawano, Shigeru,Nishiyama, Akira,Minami, Hiromichi,Katayama, Takane,Yasohara, Yoshihiko,Sato, Fumihiko,Kumagai, Hidehiko
, p. 701 - 707 (2015/07/20)
Norcoclaurine synthase (NCS) catalyzes the stereo-selective Pictet-Spengler reaction between dopamine and 4-hydroxyphenylacetaldehyde as the first step of benzylisoquinoline alkaloid synthesis in plants. Recent studies suggested that NCS shows relatively relaxed substrate specificity toward aldehydes, and thus, the enzyme can serve as a tool to synthesize unnatural, optically active tetrahydroisoquinolines. In this study, using an N-terminally truncated NCS from Coptis japonica expressed in Escherichia coli, we examined the aldehyde substrate specificity of the enzyme. Herein, we demonstrate the versatility of the enzyme by synthesizing 6,7-dihydroxy-1-phenethyl-1,2,3,4-tetrahydroisoquinoline and 6,7-dihydroxy-1-propyl-1,2,3,4-tetrahydroisoquinoline in molar yields of 86.0 and 99.6% and in enantiomer excess of 95.3 and 98.0%, respectively. The results revealed the enzyme is a promising catalyst that functions to stereoselectively produce various 1-substituted-1,2,3,4-tetrahydroisoquinolines.
Biocatalytic production of tetrahydroisoquinolines
Ruff, Bettina M.,Br?se,O'Connor, Sarah E.
supporting information; experimental part, p. 1071 - 1074 (2012/03/27)
The promiscuity of the enzyme norcoclaurine synthase is described. This biocatalyst yielded a diverse array of substituted tetrahydroisoquinolines by cyclizing dopamine with various acetaldehydes in a Pictet-Spengler reaction. This enzymatic reaction may provide a biocatalytic route to a range of tetrahydroisoquinoline alkaloids.