Formal Asymmetric Biocatalytic Reductive Amination

All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselect...

Ausführliche Beschreibung

Gespeichert in:
Bibliographische Detailangaben
Veröffentlicht in:Angewandte Chemie (International ed.) 2008-01, Vol.47 (48), p.9337-9340
Hauptverfasser: Koszelewski, Dominik, Lavandera, Iván, Clay, Dorina, Guebitz, Georg M, Rozzell, David, Kroutil, Wolfgang
Format: Artikel
Sprache:eng
Schlagworte:
Online-Zugang:Volltext
Tags: Tag hinzufügen
Keine Tags, Fügen Sie den ersten Tag hinzu!
container_end_page 9340
container_issue 48
container_start_page 9337
container_title Angewandte Chemie (International ed.)
container_volume 47
creator Koszelewski, Dominik
Lavandera, Iván
Clay, Dorina
Guebitz, Georg M
Rozzell, David
Kroutil, Wolfgang
description All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction.
doi_str_mv 10.1002/anie.200803763
format Article
fullrecord <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_69818384</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>69818384</sourcerecordid><originalsourceid>FETCH-LOGICAL-c4333-ee429a6d44f4e6f21a854d018786232b2bb96acb49be012735302d71132324ba3</originalsourceid><addsrcrecordid>eNqFkD1PwzAQhi0EoqWwMkInthTb59jOWKoWKlUgAZ0tJ3GQUT6KnYDy73GVCtiY7k733HvSg9AlwTOCMb3VtTUzirHEIDgcoTGJKYlACDgOPQOIhIzJCJ15_x54KTE_RSMiE0GZgDGiq8ZVupzOfV9VpnU2m97ZJtOtLvs2DM8m77LWfprpvLK1bm1Tn6OTQpfeXBzqBG1Xy9fFQ7R5ul8v5psoC28hMobRRPOcsYIZXlCiZcxyTKSQnAJNaZomXGcpS1KDCRUQA6a5IATClqUaJuhmyN255qMzvlWV9ZkpS12bpvOKJ5JIkCyAswHMXOO9M4XaOVtp1yuC1d6S2ltSP5bCwdUhuUsrk__iBy0BSAbgy5am_ydOzR_Xy7_h18NtoRul35z1avtCMQFMYh7HQsI3H6t7YQ</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>69818384</pqid></control><display><type>article</type><title>Formal Asymmetric Biocatalytic Reductive Amination</title><source>MEDLINE</source><source>Wiley Online Library Journals Frontfile Complete</source><creator>Koszelewski, Dominik ; Lavandera, Iván ; Clay, Dorina ; Guebitz, Georg M ; Rozzell, David ; Kroutil, Wolfgang</creator><creatorcontrib>Koszelewski, Dominik ; Lavandera, Iván ; Clay, Dorina ; Guebitz, Georg M ; Rozzell, David ; Kroutil, Wolfgang</creatorcontrib><description>All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction.</description><identifier>ISSN: 1433-7851</identifier><identifier>EISSN: 1521-3773</identifier><identifier>DOI: 10.1002/anie.200803763</identifier><identifier>PMID: 18972473</identifier><language>eng</language><publisher>Weinheim: Wiley-VCH Verlag</publisher><subject>Amination ; amines ; Amines - chemistry ; Amines - metabolism ; asymmetric catalysis ; Biocatalysis ; cascade reactions ; Ketones - chemistry ; Oxidation-Reduction ; reductive amination ; Stereoisomerism</subject><ispartof>Angewandte Chemie (International ed.), 2008-01, Vol.47 (48), p.9337-9340</ispartof><rights>Copyright © 2008 WILEY‐VCH Verlag GmbH &amp; Co. KGaA, Weinheim</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c4333-ee429a6d44f4e6f21a854d018786232b2bb96acb49be012735302d71132324ba3</citedby><cites>FETCH-LOGICAL-c4333-ee429a6d44f4e6f21a854d018786232b2bb96acb49be012735302d71132324ba3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://onlinelibrary.wiley.com/doi/pdf/10.1002%2Fanie.200803763$$EPDF$$P50$$Gwiley$$H</linktopdf><linktohtml>$$Uhttps://onlinelibrary.wiley.com/doi/full/10.1002%2Fanie.200803763$$EHTML$$P50$$Gwiley$$H</linktohtml><link.rule.ids>314,776,780,1411,27901,27902,45550,45551</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/18972473$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Koszelewski, Dominik</creatorcontrib><creatorcontrib>Lavandera, Iván</creatorcontrib><creatorcontrib>Clay, Dorina</creatorcontrib><creatorcontrib>Guebitz, Georg M</creatorcontrib><creatorcontrib>Rozzell, David</creatorcontrib><creatorcontrib>Kroutil, Wolfgang</creatorcontrib><title>Formal Asymmetric Biocatalytic Reductive Amination</title><title>Angewandte Chemie (International ed.)</title><addtitle>Angew Chem Int Ed Engl</addtitle><description>All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction.</description><subject>Amination</subject><subject>amines</subject><subject>Amines - chemistry</subject><subject>Amines - metabolism</subject><subject>asymmetric catalysis</subject><subject>Biocatalysis</subject><subject>cascade reactions</subject><subject>Ketones - chemistry</subject><subject>Oxidation-Reduction</subject><subject>reductive amination</subject><subject>Stereoisomerism</subject><issn>1433-7851</issn><issn>1521-3773</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2008</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkD1PwzAQhi0EoqWwMkInthTb59jOWKoWKlUgAZ0tJ3GQUT6KnYDy73GVCtiY7k733HvSg9AlwTOCMb3VtTUzirHEIDgcoTGJKYlACDgOPQOIhIzJCJ15_x54KTE_RSMiE0GZgDGiq8ZVupzOfV9VpnU2m97ZJtOtLvs2DM8m77LWfprpvLK1bm1Tn6OTQpfeXBzqBG1Xy9fFQ7R5ul8v5psoC28hMobRRPOcsYIZXlCiZcxyTKSQnAJNaZomXGcpS1KDCRUQA6a5IATClqUaJuhmyN255qMzvlWV9ZkpS12bpvOKJ5JIkCyAswHMXOO9M4XaOVtp1yuC1d6S2ltSP5bCwdUhuUsrk__iBy0BSAbgy5am_ydOzR_Xy7_h18NtoRul35z1avtCMQFMYh7HQsI3H6t7YQ</recordid><startdate>20080101</startdate><enddate>20080101</enddate><creator>Koszelewski, Dominik</creator><creator>Lavandera, Iván</creator><creator>Clay, Dorina</creator><creator>Guebitz, Georg M</creator><creator>Rozzell, David</creator><creator>Kroutil, Wolfgang</creator><general>Wiley-VCH Verlag</general><general>WILEY‐VCH Verlag</general><scope>FBQ</scope><scope>CGR</scope><scope>CUY</scope><scope>CVF</scope><scope>ECM</scope><scope>EIF</scope><scope>NPM</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7X8</scope></search><sort><creationdate>20080101</creationdate><title>Formal Asymmetric Biocatalytic Reductive Amination</title><author>Koszelewski, Dominik ; Lavandera, Iván ; Clay, Dorina ; Guebitz, Georg M ; Rozzell, David ; Kroutil, Wolfgang</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c4333-ee429a6d44f4e6f21a854d018786232b2bb96acb49be012735302d71132324ba3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2008</creationdate><topic>Amination</topic><topic>amines</topic><topic>Amines - chemistry</topic><topic>Amines - metabolism</topic><topic>asymmetric catalysis</topic><topic>Biocatalysis</topic><topic>cascade reactions</topic><topic>Ketones - chemistry</topic><topic>Oxidation-Reduction</topic><topic>reductive amination</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Koszelewski, Dominik</creatorcontrib><creatorcontrib>Lavandera, Iván</creatorcontrib><creatorcontrib>Clay, Dorina</creatorcontrib><creatorcontrib>Guebitz, Georg M</creatorcontrib><creatorcontrib>Rozzell, David</creatorcontrib><creatorcontrib>Kroutil, Wolfgang</creatorcontrib><collection>AGRIS</collection><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>MEDLINE - Academic</collection><jtitle>Angewandte Chemie (International ed.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Koszelewski, Dominik</au><au>Lavandera, Iván</au><au>Clay, Dorina</au><au>Guebitz, Georg M</au><au>Rozzell, David</au><au>Kroutil, Wolfgang</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Formal Asymmetric Biocatalytic Reductive Amination</atitle><jtitle>Angewandte Chemie (International ed.)</jtitle><addtitle>Angew Chem Int Ed Engl</addtitle><date>2008-01-01</date><risdate>2008</risdate><volume>47</volume><issue>48</issue><spage>9337</spage><epage>9340</epage><pages>9337-9340</pages><issn>1433-7851</issn><eissn>1521-3773</eissn><abstract>All for one: A combination of three biocatalysts (ω‐transaminase, alanine dehydrogenase, and an enzyme such as formate dehydrogenase for cofactor recycling) catalyze a cascade to achieve the asymmetric transformation of a ketone into a primary α‐chiral unprotected amine through a formal stereoselective reductive amination (see scheme). Only ammonia and the reducing agent (formate) are consumed during this reaction.</abstract><cop>Weinheim</cop><pub>Wiley-VCH Verlag</pub><pmid>18972473</pmid><doi>10.1002/anie.200803763</doi><tpages>4</tpages></addata></record>
fulltext fulltext
identifier ISSN: 1433-7851
ispartof Angewandte Chemie (International ed.), 2008-01, Vol.47 (48), p.9337-9340
issn 1433-7851
1521-3773
language eng
recordid cdi_proquest_miscellaneous_69818384
source MEDLINE; Wiley Online Library Journals Frontfile Complete
subjects Amination
amines
Amines - chemistry
Amines - metabolism
asymmetric catalysis
Biocatalysis
cascade reactions
Ketones - chemistry
Oxidation-Reduction
reductive amination
Stereoisomerism
title Formal Asymmetric Biocatalytic Reductive Amination
url https://sfx.bib-bvb.de/sfx_tum?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-02-08T21%3A38%3A26IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Formal%20Asymmetric%20Biocatalytic%20Reductive%20Amination&rft.jtitle=Angewandte%20Chemie%20(International%20ed.)&rft.au=Koszelewski,%20Dominik&rft.date=2008-01-01&rft.volume=47&rft.issue=48&rft.spage=9337&rft.epage=9340&rft.pages=9337-9340&rft.issn=1433-7851&rft.eissn=1521-3773&rft_id=info:doi/10.1002/anie.200803763&rft_dat=%3Cproquest_cross%3E69818384%3C/proquest_cross%3E%3Curl%3E%3C/url%3E&disable_directlink=true&sfx.directlink=off&sfx.report_link=0&rft_id=info:oai/&rft_pqid=69818384&rft_id=info:pmid/18972473&rfr_iscdi=true