Loading…
Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol
Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate usi...
Saved in:
Published in: | Chirality (New York, N.Y.) N.Y.), 2022-02, Vol.34 (2), p.428-437 |
---|---|
Main Authors: | , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
cited_by | cdi_FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553 |
---|---|
cites | cdi_FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553 |
container_end_page | 437 |
container_issue | 2 |
container_start_page | 428 |
container_title | Chirality (New York, N.Y.) |
container_volume | 34 |
creator | Hebda, Paulina Wiśniowska, Lilianna Szafrański, Przemysław W. Cegła, Marek |
description | Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative‐scale process: temperature, organic co‐solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc‐Cl) derivatization protocol for 2‐azidocyclohexanol, which enabled chiral reversed‐phase high‐performance liquid chromatography (RP‐HPLC) determination of enantiomeric excess. |
doi_str_mv | 10.1002/chir.23397 |
format | article |
fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_2601483700</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><sourcerecordid>2601483700</sourcerecordid><originalsourceid>FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553</originalsourceid><addsrcrecordid>eNp90UFu1DAUBmALgehQ2HAAFIkNQkp5tuM4XqJRYSoNAiGQ2EUe-4VxceLBToB0xRE4AmfjJDhMYcGiC-ttPv-y30_IQwpnFIA9M3sXzxjnSt4iKyoYlDWvP9wmK2iUKgEqdkLupXQJAKrm1V1ywquGckrFivx8NfnRfYy6__X9RzLaY4HD1dzr0ZnikxtwmRFT8NPowlCErhijHlLWLB995Wwws_Fhj99mX2iDox6x0IMtlmdpny9_wZjQZn3Y64TF5s12nYH2c3LpxkA9BH-f3Om0T_jgep6S9y_O36035fb1y4v1821puJCyZLKqRKN21thGWCUsNV2HpgZhpW0UQtVwtatQ1Y0ynVVgKm2srKCWO4ZC8FPy5Jh7iOHzhGlse5cMeq8HDFNqWQ00Z0iATB__Ry_DFPOHFsUYlxLEop4elYkhpYhde4iu13FuKbRLb-2yoPZPbxk_uo6cdj3af_RvURnQI_jqPM43RLXrzcXbY-hvALKsQA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>2622377050</pqid></control><display><type>article</type><title>Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol</title><source>Wiley-Blackwell Read & Publish Collection</source><creator>Hebda, Paulina ; Wiśniowska, Lilianna ; Szafrański, Przemysław W. ; Cegła, Marek</creator><creatorcontrib>Hebda, Paulina ; Wiśniowska, Lilianna ; Szafrański, Przemysław W. ; Cegła, Marek</creatorcontrib><description>Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative‐scale process: temperature, organic co‐solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc‐Cl) derivatization protocol for 2‐azidocyclohexanol, which enabled chiral reversed‐phase high‐performance liquid chromatography (RP‐HPLC) determination of enantiomeric excess.</description><identifier>ISSN: 0899-0042</identifier><identifier>EISSN: 1520-636X</identifier><identifier>DOI: 10.1002/chir.23397</identifier><identifier>PMID: 34813115</identifier><language>eng</language><publisher>United States: Wiley Subscription Services, Inc</publisher><subject>2‐azidocyclohexanol ; Acetates ; Acetic acid ; Alcohols ; Amines ; Calcium ions ; chiral RP‐HPLC ; Chromatography, High Pressure Liquid - methods ; Fmoc derivatization ; Fmoc ester ; High performance liquid chromatography ; hydrolytic kinetic resolution ; Lipase ; Lipase - chemistry ; Liquid chromatography ; Stereoisomerism</subject><ispartof>Chirality (New York, N.Y.), 2022-02, Vol.34 (2), p.428-437</ispartof><rights>2021 Wiley Periodicals LLC.</rights><rights>2022 Wiley Periodicals LLC.</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553</citedby><cites>FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553</cites><orcidid>0000-0002-7014-809X ; 0000-0002-3760-5500</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,776,780,27901,27902</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/34813115$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Hebda, Paulina</creatorcontrib><creatorcontrib>Wiśniowska, Lilianna</creatorcontrib><creatorcontrib>Szafrański, Przemysław W.</creatorcontrib><creatorcontrib>Cegła, Marek</creatorcontrib><title>Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol</title><title>Chirality (New York, N.Y.)</title><addtitle>Chirality</addtitle><description>Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative‐scale process: temperature, organic co‐solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc‐Cl) derivatization protocol for 2‐azidocyclohexanol, which enabled chiral reversed‐phase high‐performance liquid chromatography (RP‐HPLC) determination of enantiomeric excess.</description><subject>2‐azidocyclohexanol</subject><subject>Acetates</subject><subject>Acetic acid</subject><subject>Alcohols</subject><subject>Amines</subject><subject>Calcium ions</subject><subject>chiral RP‐HPLC</subject><subject>Chromatography, High Pressure Liquid - methods</subject><subject>Fmoc derivatization</subject><subject>Fmoc ester</subject><subject>High performance liquid chromatography</subject><subject>hydrolytic kinetic resolution</subject><subject>Lipase</subject><subject>Lipase - chemistry</subject><subject>Liquid chromatography</subject><subject>Stereoisomerism</subject><issn>0899-0042</issn><issn>1520-636X</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2022</creationdate><recordtype>article</recordtype><recordid>eNp90UFu1DAUBmALgehQ2HAAFIkNQkp5tuM4XqJRYSoNAiGQ2EUe-4VxceLBToB0xRE4AmfjJDhMYcGiC-ttPv-y30_IQwpnFIA9M3sXzxjnSt4iKyoYlDWvP9wmK2iUKgEqdkLupXQJAKrm1V1ywquGckrFivx8NfnRfYy6__X9RzLaY4HD1dzr0ZnikxtwmRFT8NPowlCErhijHlLWLB995Wwws_Fhj99mX2iDox6x0IMtlmdpny9_wZjQZn3Y64TF5s12nYH2c3LpxkA9BH-f3Om0T_jgep6S9y_O36035fb1y4v1821puJCyZLKqRKN21thGWCUsNV2HpgZhpW0UQtVwtatQ1Y0ynVVgKm2srKCWO4ZC8FPy5Jh7iOHzhGlse5cMeq8HDFNqWQ00Z0iATB__Ry_DFPOHFsUYlxLEop4elYkhpYhde4iu13FuKbRLb-2yoPZPbxk_uo6cdj3af_RvURnQI_jqPM43RLXrzcXbY-hvALKsQA</recordid><startdate>202202</startdate><enddate>202202</enddate><creator>Hebda, Paulina</creator><creator>Wiśniowska, Lilianna</creator><creator>Szafrański, Przemysław W.</creator><creator>Cegła, Marek</creator><general>Wiley Subscription Services, Inc</general><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>7QO</scope><scope>7QR</scope><scope>7U7</scope><scope>8FD</scope><scope>C1K</scope><scope>FR3</scope><scope>P64</scope><scope>7X8</scope><orcidid>https://orcid.org/0000-0002-7014-809X</orcidid><orcidid>https://orcid.org/0000-0002-3760-5500</orcidid></search><sort><creationdate>202202</creationdate><title>Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol</title><author>Hebda, Paulina ; Wiśniowska, Lilianna ; Szafrański, Przemysław W. ; Cegła, Marek</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2022</creationdate><topic>2‐azidocyclohexanol</topic><topic>Acetates</topic><topic>Acetic acid</topic><topic>Alcohols</topic><topic>Amines</topic><topic>Calcium ions</topic><topic>chiral RP‐HPLC</topic><topic>Chromatography, High Pressure Liquid - methods</topic><topic>Fmoc derivatization</topic><topic>Fmoc ester</topic><topic>High performance liquid chromatography</topic><topic>hydrolytic kinetic resolution</topic><topic>Lipase</topic><topic>Lipase - chemistry</topic><topic>Liquid chromatography</topic><topic>Stereoisomerism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Hebda, Paulina</creatorcontrib><creatorcontrib>Wiśniowska, Lilianna</creatorcontrib><creatorcontrib>Szafrański, Przemysław W.</creatorcontrib><creatorcontrib>Cegła, Marek</creatorcontrib><collection>Medline</collection><collection>MEDLINE</collection><collection>MEDLINE (Ovid)</collection><collection>MEDLINE</collection><collection>MEDLINE</collection><collection>PubMed</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Chemoreception Abstracts</collection><collection>Toxicology Abstracts</collection><collection>Technology Research Database</collection><collection>Environmental Sciences and Pollution Management</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Chirality (New York, N.Y.)</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Hebda, Paulina</au><au>Wiśniowska, Lilianna</au><au>Szafrański, Przemysław W.</au><au>Cegła, Marek</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol</atitle><jtitle>Chirality (New York, N.Y.)</jtitle><addtitle>Chirality</addtitle><date>2022-02</date><risdate>2022</risdate><volume>34</volume><issue>2</issue><spage>428</spage><epage>437</epage><pages>428-437</pages><issn>0899-0042</issn><eissn>1520-636X</eissn><abstract>Lipase‐catalyzed hydrolytic kinetic resolution is a method of obtaining optically pure chiral alcohols and amines, which requires additional tools for determining enantiomerical purity. Herein, we present a study on multigram‐scale hydrolytic kinetic resolution of trans‐2‐azidocyclohexyl acetate using Pseudomonas cepacia lipase immobilized on Immobead support. We investigated several parameters of the preparative‐scale process: temperature, organic co‐solvent, and the influence of calcium ions. Moreover, we have developed an efficient fluorenylmethyloxycarbonyl chloride (Fmoc‐Cl) derivatization protocol for 2‐azidocyclohexanol, which enabled chiral reversed‐phase high‐performance liquid chromatography (RP‐HPLC) determination of enantiomeric excess.</abstract><cop>United States</cop><pub>Wiley Subscription Services, Inc</pub><pmid>34813115</pmid><doi>10.1002/chir.23397</doi><tpages>10</tpages><orcidid>https://orcid.org/0000-0002-7014-809X</orcidid><orcidid>https://orcid.org/0000-0002-3760-5500</orcidid></addata></record> |
fulltext | fulltext |
identifier | ISSN: 0899-0042 |
ispartof | Chirality (New York, N.Y.), 2022-02, Vol.34 (2), p.428-437 |
issn | 0899-0042 1520-636X |
language | eng |
recordid | cdi_proquest_miscellaneous_2601483700 |
source | Wiley-Blackwell Read & Publish Collection |
subjects | 2‐azidocyclohexanol Acetates Acetic acid Alcohols Amines Calcium ions chiral RP‐HPLC Chromatography, High Pressure Liquid - methods Fmoc derivatization Fmoc ester High performance liquid chromatography hydrolytic kinetic resolution Lipase Lipase - chemistry Liquid chromatography Stereoisomerism |
title | Multigram‐scale enzymatic kinetic resolution of trans‐2‐azidocyclohexyl acetate and chiral reversed‐phase HPLC analysis of trans‐2‐azidocyclohexanol |
url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-30T04%3A14%3A09IST&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=Multigram%E2%80%90scale%20enzymatic%20kinetic%20resolution%20of%20trans%E2%80%902%E2%80%90azidocyclohexyl%20acetate%20and%20chiral%20reversed%E2%80%90phase%20HPLC%20analysis%20of%20trans%E2%80%902%E2%80%90azidocyclohexanol&rft.jtitle=Chirality%20(New%20York,%20N.Y.)&rft.au=Hebda,%20Paulina&rft.date=2022-02&rft.volume=34&rft.issue=2&rft.spage=428&rft.epage=437&rft.pages=428-437&rft.issn=0899-0042&rft.eissn=1520-636X&rft_id=info:doi/10.1002/chir.23397&rft_dat=%3Cproquest_cross%3E2601483700%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c3577-2744589bdcd85d95d1cffec605d7d89e04839b4e9689cfd90c4acd74067b2e553%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=2622377050&rft_id=info:pmid/34813115&rfr_iscdi=true |