Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction

James L. Galman; Iustina Slabu; Fabio Parmeggiani; Nicholas J. Turner

doi:10.1039/C8CC06759G

Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction

James L. Galman, Iustina Slabu, Fabio Parmeggiani, Nicholas J. Turner^*

^*Corresponding author for this work

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Abstract

Heterocycles based on piperidine and pyrrolidine are key moieties in natural products and pharmaceutically active molecules. A novel multi-enzymatic approach based on the combination of a lipase with an α,ω-diamine transaminase is reported, opening up the synthesis, isolation and characterisation of a broad range of 2-substituted N-heterocycle alkaloids.

Original language	English
Pages (from-to)	11316-11319
Number of pages	4
Journal	Chemical Communications
Volume	54
Issue number	80
Early online date	17 Sept 2018
DOIs	https://doi.org/10.1039/C8CC06759G
Publication status	Published - 2018

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Manchester Institute of Biotechnology

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10.1039/C8CC06759G

Galman et al - Alkaloids lipase-TA (manuscript)_acceptedAccepted author manuscript, 3.26 MB

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title = "Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction",

abstract = "Heterocycles based on piperidine and pyrrolidine are key moieties in natural products and pharmaceutically active molecules. A novel multi-enzymatic approach based on the combination of a lipase with an α,ω-diamine transaminase is reported, opening up the synthesis, isolation and characterisation of a broad range of 2-substituted N-heterocycle alkaloids.",

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AU - Galman, James L.

AU - Slabu, Iustina

AU - Parmeggiani, Fabio

AU - Turner, Nicholas J.

PY - 2018

Y1 - 2018

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AB - Heterocycles based on piperidine and pyrrolidine are key moieties in natural products and pharmaceutically active molecules. A novel multi-enzymatic approach based on the combination of a lipase with an α,ω-diamine transaminase is reported, opening up the synthesis, isolation and characterisation of a broad range of 2-substituted N-heterocycle alkaloids.

U2 - 10.1039/C8CC06759G

DO - 10.1039/C8CC06759G

M3 - Article

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SN - 1359-7345

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EP - 11319

JO - Chemical Communications

JF - Chemical Communications

IS - 80

ER -

Biomimetic synthesis of 2-substituted N-heterocycle alkaloids by one-pot hydrolysis, transamination and decarboxylative Mannich reaction

Abstract

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