The Pictet–Spengler reaction in nature and in organic chemistry
J Stöckigt, AP Antonchick, F Wu… - Angewandte Chemie …, 2011 - Wiley Online Library
Alkaloids are an important class of natural products that are widely distributed in nature and
produced by a large variety of organisms. They have a wide spectrum of biological activity …
produced by a large variety of organisms. They have a wide spectrum of biological activity …
Evolutionary and cellular webs in benzylisoquinoline alkaloid biosynthesis
DK Liscombe, PJ Facchini - Current Opinion in Biotechnology, 2008 - Elsevier
Alkaloids are a group of approximately 12000 low molecular weight and nitrogenous
secondary metabolites found in 20% of plant species. Their potent biological activity …
secondary metabolites found in 20% of plant species. Their potent biological activity …
Microbial production of plant benzylisoquinoline alkaloids
H Minami, JS Kim, N Ikezawa… - Proceedings of the …, 2008 - National Acad Sciences
Benzylisoquinoline alkaloids, such as the analgesic compounds morphine and codeine, and
the antibacterial agents berberine, palmatine, and magnoflorine, are synthesized from …
the antibacterial agents berberine, palmatine, and magnoflorine, are synthesized from …
Enzyme catalysed Pictet-Spengler formation of chiral 1, 1'-disubstituted-and spiro-tetrahydroisoquinolines
BR Lichman, J Zhao, HC Hailes, JM Ward - Nature communications, 2017 - nature.com
Abstract The Pictet–Spengler reaction (PSR) involves the condensation and ring closure
between a β-arylethylamine and a carbonyl compound. The combination of dopamine and …
between a β-arylethylamine and a carbonyl compound. The combination of dopamine and …
'Dopamine‐first'mechanism enables the rational engineering of the norcoclaurine synthase aldehyde activity profile
BR Lichman, MC Gershater, ED Lamming… - The FEBS …, 2015 - Wiley Online Library
Norcoclaurine synthase (NCS)(EC 4.2. 1.78) catalyzes the Pictet–Spengler condensation of
dopamine and an aldehyde, forming a substituted (S)‐tetrahydroisoquinoline, a …
dopamine and an aldehyde, forming a substituted (S)‐tetrahydroisoquinoline, a …
The Catalytic Potential of Coptis japonica NCS2 Revealed – Development and Utilisation of a Fluorescamine‐Based Assay
The versatility and potential of a norcoclaurine synthase (NCS) from Coptis japonica NCS2
has been investigated, together with the development and application of a novel …
has been investigated, together with the development and application of a novel …
Asymmetric synthesis of tetrahydroisoquinolines by enzymatic Pictet–Spengler reaction
M Nishihachijo, Y Hirai, S Kawano… - Bioscience …, 2014 - academic.oup.com
Norcoclaurine synthase (NCS) catalyzes the stereoselective Pictet–Spengler reaction
between dopamine and 4-hydroxyphenylacetaldehyde as the first step of benzylisoquinoline …
between dopamine and 4-hydroxyphenylacetaldehyde as the first step of benzylisoquinoline …
Construction of biocatalytic cascades for the synthesis of benzylisoquinoline alkaloids from p-coumaric acid derivatives and dopamine
M Zhao, Z Qin, A Abdullah, Y Xiao - Green Chemistry, 2022 - pubs.rsc.org
Benzylisoquinoline alkaloids (BIAs) are an important family of plant-derived metabolites with
diverse biological activities. Owing to their structural complexity and high stereoselectivity …
diverse biological activities. Owing to their structural complexity and high stereoselectivity …
Biocatalyzed C− C bond formation for the production of alkaloids
Traditional methods of chemical synthesis of alkaloids exhibit various problems such as lack
of enantioselectivity, the use of toxic chemical and intermediates, and multiple numbers of …
of enantioselectivity, the use of toxic chemical and intermediates, and multiple numbers of …
Modular assembly of an artificially concise biocatalytic cascade for the manufacture of phenethylisoquinoline alkaloids
Y Gao, F Li, Z Luo, Z Deng, Y Zhang, Z Yuan… - Nature …, 2024 - nature.com
Plant-derived alkaloids are an important class of pharmaceuticals. However, they still rely on
phytoextraction to meet their diverse market demands. Since multistep biocatalytic cascades …
phytoextraction to meet their diverse market demands. Since multistep biocatalytic cascades …