Cargando…

Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts

[Image: see text] This account focuses on the application of ω-transaminases, lyases, and oxidases for the preparation of amines considering mainly work from our own lab. Examples are given to access α-chiral primary amines from the corresponding ketones as well as terminal amines from primary alcoh...

Descripción completa

Detalles Bibliográficos
Autores principales: Kroutil, Wolfgang, Fischereder, Eva-Maria, Fuchs, Christine S., Lechner, Horst, Mutti, Francesco G., Pressnitz, Desiree, Rajagopalan, Aashrita, Sattler, Johann H., Simon, Robert C., Siirola, Elina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2013
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3688330/
https://www.ncbi.nlm.nih.gov/pubmed/23794796
http://dx.doi.org/10.1021/op4000237
_version_ 1782476181171339264
author Kroutil, Wolfgang
Fischereder, Eva-Maria
Fuchs, Christine S.
Lechner, Horst
Mutti, Francesco G.
Pressnitz, Desiree
Rajagopalan, Aashrita
Sattler, Johann H.
Simon, Robert C.
Siirola, Elina
author_facet Kroutil, Wolfgang
Fischereder, Eva-Maria
Fuchs, Christine S.
Lechner, Horst
Mutti, Francesco G.
Pressnitz, Desiree
Rajagopalan, Aashrita
Sattler, Johann H.
Simon, Robert C.
Siirola, Elina
author_sort Kroutil, Wolfgang
collection PubMed
description [Image: see text] This account focuses on the application of ω-transaminases, lyases, and oxidases for the preparation of amines considering mainly work from our own lab. Examples are given to access α-chiral primary amines from the corresponding ketones as well as terminal amines from primary alcohols via a two-step biocascade. 2,6-Disubstituted piperidines, as examples for secondary amines, are prepared by biocatalytical regioselective asymmetric monoamination of designated diketones followed by spontaneous ring closure and a subsequent diastereoselective reduction step. Optically pure tert-amines such as berbines and N-methyl benzylisoquinolines are obtained by kinetic resolution via an enantioselective aerobic oxidative C–C bond formation.
format Online
Article
Text
id pubmed-3688330
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher American Chemical Society
record_format MEDLINE/PubMed
spelling pubmed-36883302013-06-21 Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts Kroutil, Wolfgang Fischereder, Eva-Maria Fuchs, Christine S. Lechner, Horst Mutti, Francesco G. Pressnitz, Desiree Rajagopalan, Aashrita Sattler, Johann H. Simon, Robert C. Siirola, Elina Org Process Res Dev [Image: see text] This account focuses on the application of ω-transaminases, lyases, and oxidases for the preparation of amines considering mainly work from our own lab. Examples are given to access α-chiral primary amines from the corresponding ketones as well as terminal amines from primary alcohols via a two-step biocascade. 2,6-Disubstituted piperidines, as examples for secondary amines, are prepared by biocatalytical regioselective asymmetric monoamination of designated diketones followed by spontaneous ring closure and a subsequent diastereoselective reduction step. Optically pure tert-amines such as berbines and N-methyl benzylisoquinolines are obtained by kinetic resolution via an enantioselective aerobic oxidative C–C bond formation. American Chemical Society 2013-04-22 2013-05-17 /pmc/articles/PMC3688330/ /pubmed/23794796 http://dx.doi.org/10.1021/op4000237 Text en Copyright © 2013 American Chemical Society Terms of Use (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html)
spellingShingle Kroutil, Wolfgang
Fischereder, Eva-Maria
Fuchs, Christine S.
Lechner, Horst
Mutti, Francesco G.
Pressnitz, Desiree
Rajagopalan, Aashrita
Sattler, Johann H.
Simon, Robert C.
Siirola, Elina
Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
title Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
title_full Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
title_fullStr Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
title_full_unstemmed Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
title_short Asymmetric Preparation of prim-, sec-, and tert-Amines Employing Selected Biocatalysts
title_sort asymmetric preparation of prim-, sec-, and tert-amines employing selected biocatalysts
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3688330/
https://www.ncbi.nlm.nih.gov/pubmed/23794796
http://dx.doi.org/10.1021/op4000237
work_keys_str_mv AT kroutilwolfgang asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT fischerederevamaria asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT fuchschristines asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT lechnerhorst asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT muttifrancescog asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT pressnitzdesiree asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT rajagopalanaashrita asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT sattlerjohannh asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT simonrobertc asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts
AT siirolaelina asymmetricpreparationofprimsecandtertaminesemployingselectedbiocatalysts