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 …

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 …

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 …

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 …

'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 …

The Catalytic Potential of Coptis japonica NCS2 Revealed – Development and Utilisation of a Fluorescamine‐Based Assay

T Pesnot, MC Gershater, JM Ward… - Advanced Synthesis & …, 2012 - Wiley Online Library
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 …

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 …

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 …

Biocatalyzed C− C bond formation for the production of alkaloids

MD Patil, G Grogan, H Yun - ChemCatChem, 2018 - Wiley Online Library
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 …

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 …