A facile and regioselective multicomponent synthesis of chiral aryl-1,2-mercaptoamines in water followed by monoamine oxidase (MAO-N) enzymatic resolution.

Amines / chemical synthesis Biocatalysis Microwaves Models, Molecular Molecular Structure Monoamine Oxidase / chemistry Stereoisomerism Water / chemistry

Journal

Organic & biomolecular chemistry
ISSN: 1477-0539
Titre abrégé: Org Biomol Chem
Pays: England
ID NLM: 101154995

Informations de publication

Date de publication:
28 10 2019
Historique:
pubmed: 5 10 2019
medline: 14 1 2020
entrez: 5 10 2019
Statut: ppublish

Résumé

A facile microwave assisted three-component protocol allows the synthesis of chiral aryl-1,2-mercaptoamines in water in a few minutes with high yields, bypassing the use of toxic aziridine intermediates. The chiral 1,2-mercaptoamines were then deracemized through enzymatic resolution of the racemates using monoamine oxidase (MAO-N) biocatalysts.

Identifiants

DOI: 10.1039/c9ob01962f PMID: 31584061
pubmed: 31584061
doi: 10.1039/c9ob01962f
doi:

Substances chimiques

Amines 0
Water 059QF0KO0R
Monoamine Oxidase EC 1.4.3.4

Types de publication

Journal Article Research Support, Non-U.S. Gov't

Langues

eng

Sous-ensembles de citation

IM

Pagination

8982-8986

Auteurs

Kate Lauder (K)

School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, SE1 9NH, London, UK. daniele.castagnolo@kcl.ac.uk.
ORCID: 0000-0002-9318-7518

Domiziana Masci (D)

School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, SE1 9NH, London, UK. daniele.castagnolo@kcl.ac.uk.

Anita Toscani (A)

School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, SE1 9NH, London, UK. daniele.castagnolo@kcl.ac.uk.

Aya Al Mekdad (A)

School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, SE1 9NH, London, UK. daniele.castagnolo@kcl.ac.uk.

Gary W Black (GW)

Department of Applied Sciences, Northumbria University, Ellison Place, NE1 8ST, Newcastle upon Tyne, UK.
ORCID: 0000-0003-3697-0714

Nicola L Brown (NL)

Department of Applied Sciences, Northumbria University, Ellison Place, NE1 8ST, Newcastle upon Tyne, UK.

Nicholas J Turner (NJ)

School of Chemistry, Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, M1 7DN, Manchester, UK.
ORCID: 0000-0002-8708-0781

Renzo Luisi (R)

Department of Pharmacy - Drug Sciences, University of Bari"A. Moro", Via E. Orabona 4, Bari 70125, Italy.
ORCID: 0000-0002-9882-7908

Daniele Castagnolo (D)

School of Cancer and Pharmaceutical Sciences, King's College London, 150 Stamford Street, SE1 9NH, London, UK. daniele.castagnolo@kcl.ac.uk.
ORCID: 0000-0002-7517-5732

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Classifications MeSH

questionsmedicales.fr › Composés chimiques organiques › Amines › A facile and regioselective multicomponent...
questionsmedicales.fr › Métabolisme › Biocatalyse › A facile and regioselective multicomponent...
questionsmedicales.fr › Phénomènes physiques › Rayonnement › Rayonnement non ionisant › Ondes hertziennes › Micro-ondes › A facile and regioselective multicomponent...
questionsmedicales.fr › Techniques d'investigation › Modèles théoriques › Modèles moléculaires › A facile and regioselective multicomponent...
questionsmedicales.fr › Phénomènes chimiques › Structure moléculaire › A facile and regioselective multicomponent...
questionsmedicales.fr › Enzymes et coenzymes › Enzymes › Oxidoreductases › Oxidoreductases acting on CH-NH2 group donors › Monoamine oxidase › A facile and regioselective multicomponent...
questionsmedicales.fr › Phénomènes chimiques › Phénomènes de chimie organique › Isomérie › Stéréoisomérie › A facile and regioselective multicomponent...
questionsmedicales.fr › Produits chimiques inorganiques › Composés de l'oxygène › Oxydes › Eau › A facile and regioselective multicomponent...