Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of tetrahydropyran-2-methanol
(±)-Tetrahydropyran-2-methanol ( 1) was successfully resolved into both enantiomers on a preparative scale after optimization by hydrolysis of its butyrate ester (±)- 3 to ( R)-(−)- 3 (ee ⩾ 99%). The antipodal alcohol ( S)-(+)- 1 (ee ⩾ 95%) was obtained after recycling of the moderately S-enriched 1...
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| Veröffentlicht in: | Enzyme and microbial technology 1996, Vol.19 (5), p.361-366 |
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| container_issue | 5 |
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| container_title | Enzyme and microbial technology |
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| creator | Kwatelai Quartey, E.G. Hustad, Jan A. Faber, Kurt Anthonsen, Thorleif |
| description | (±)-Tetrahydropyran-2-methanol (
1) was successfully resolved into both enantiomers on a preparative scale after optimization by hydrolysis of its butyrate ester (±)-
3 to (
R)-(−)-
3 (ee ⩾ 99%). The antipodal alcohol (
S)-(+)-
1 (ee ⩾ 95%) was obtained after recycling of the moderately
S-enriched
1 to the butyrate ester
3 and subsequent hydrolysis. A fourfold increase in enantioselectivity (
E value = 24) was observed when hydrolysis was performed using one of the fractions. Tetrahydrofurfuryl alcohol (
2) could not be resolved since the best selectivity attained was
E = 3.1 from hydrolysis by the lipase B of
Candida antarctica. Resolution by transesterification was found to be unsuitable for both compounds. |
| doi_str_mv | 10.1016/S0141-0229(96)00029-4 |
| format | Article |
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1) was successfully resolved into both enantiomers on a preparative scale after optimization by hydrolysis of its butyrate ester (±)-
3 to (
R)-(−)-
3 (ee ⩾ 99%). The antipodal alcohol (
S)-(+)-
1 (ee ⩾ 95%) was obtained after recycling of the moderately
S-enriched
1 to the butyrate ester
3 and subsequent hydrolysis. A fourfold increase in enantioselectivity (
E value = 24) was observed when hydrolysis was performed using one of the fractions. Tetrahydrofurfuryl alcohol (
2) could not be resolved since the best selectivity attained was
E = 3.1 from hydrolysis by the lipase B of
Candida antarctica. Resolution by transesterification was found to be unsuitable for both compounds.</description><identifier>ISSN: 0141-0229</identifier><identifier>EISSN: 1879-0909</identifier><identifier>DOI: 10.1016/S0141-0229(96)00029-4</identifier><identifier>CODEN: EMTED2</identifier><language>eng</language><publisher>Amsterdam: Elsevier Inc</publisher><subject>Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; enantiospecificity ; Fundamental and applied biological sciences. Psychology ; lipase ; Methods. Procedures. Technologies ; Steapsin ; tetrahydropyran-2-methanol</subject><ispartof>Enzyme and microbial technology, 1996, Vol.19 (5), p.361-366</ispartof><rights>1996</rights><rights>1996 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c403t-9cf343a64cfc5a6c8a6e93f490f813f0b5772c0730f2f6826d43238e155191e13</citedby><cites>FETCH-LOGICAL-c403t-9cf343a64cfc5a6c8a6e93f490f813f0b5772c0730f2f6826d43238e155191e13</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktohtml>$$Uhttps://dx.doi.org/10.1016/S0141-0229(96)00029-4$$EHTML$$P50$$Gelsevier$$H</linktohtml><link.rule.ids>314,780,784,3550,4024,27923,27924,27925,45995</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=3233386$$DView record in Pascal Francis$$Hfree_for_read</backlink></links><search><creatorcontrib>Kwatelai Quartey, E.G.</creatorcontrib><creatorcontrib>Hustad, Jan A.</creatorcontrib><creatorcontrib>Faber, Kurt</creatorcontrib><creatorcontrib>Anthonsen, Thorleif</creatorcontrib><title>Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of tetrahydropyran-2-methanol</title><title>Enzyme and microbial technology</title><description>(±)-Tetrahydropyran-2-methanol (
1) was successfully resolved into both enantiomers on a preparative scale after optimization by hydrolysis of its butyrate ester (±)-
3 to (
R)-(−)-
3 (ee ⩾ 99%). The antipodal alcohol (
S)-(+)-
1 (ee ⩾ 95%) was obtained after recycling of the moderately
S-enriched
1 to the butyrate ester
3 and subsequent hydrolysis. A fourfold increase in enantioselectivity (
E value = 24) was observed when hydrolysis was performed using one of the fractions. Tetrahydrofurfuryl alcohol (
2) could not be resolved since the best selectivity attained was
E = 3.1 from hydrolysis by the lipase B of
Candida antarctica. Resolution by transesterification was found to be unsuitable for both compounds.</description><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>enantiospecificity</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>lipase</subject><subject>Methods. Procedures. Technologies</subject><subject>Steapsin</subject><subject>tetrahydropyran-2-methanol</subject><issn>0141-0229</issn><issn>1879-0909</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>1996</creationdate><recordtype>article</recordtype><recordid>eNqFkc9q3DAQxkVoIZs0j1DwIZT04FayZK2VSyih_yCQwKZnMSuPsgq2tJW0Aedl8qqVd0OuPQjBzG9mvpmPkI-MfmGUya8rygSradOoCyU_U0obVYsjsmDdUtVUUfWOLN6QY3KS0mOBmBB0QV5WOKDJ7snlqUK_AW9wRJ-rYKu7u5vaQIZhesa-ipjCsMsu-Go9o8_TiJWNYOYQ7OPg-2rE3u3Gkn9wHjE6_3BZrSafN5gwzV3XIW9KGnwpGTHuYxlzhM3Ux7CdIvi6qUfMRUsYPpD3FoaEZ6__Kfnz4_v99a_65vbn7-tvRaCgPNfKWC44SGGsaUGaDiQqboWitmPc0nW7XDaGLjm1jZVdI3vBG94ha1umGDJ-Sj4d-m5j-LvDlPXoksFhAI9hlzQrDbryCtgeQBNDShGt3kY3Qpw0o3q2Q-_t0POttZJ6b4cWpe78dQAkA0M5nDcuvRUXNZx3smBXBwzLsk8Oo07GYTGld7H4pPvg_jPoH1Dxom0</recordid><startdate>1996</startdate><enddate>1996</enddate><creator>Kwatelai Quartey, E.G.</creator><creator>Hustad, Jan A.</creator><creator>Faber, Kurt</creator><creator>Anthonsen, Thorleif</creator><general>Elsevier Inc</general><general>Elsevier Science</general><scope>IQODW</scope><scope>AAYXX</scope><scope>CITATION</scope><scope>7QO</scope><scope>8FD</scope><scope>FR3</scope><scope>P64</scope></search><sort><creationdate>1996</creationdate><title>Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of tetrahydropyran-2-methanol</title><author>Kwatelai Quartey, E.G. ; Hustad, Jan A. ; Faber, Kurt ; Anthonsen, Thorleif</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c403t-9cf343a64cfc5a6c8a6e93f490f813f0b5772c0730f2f6826d43238e155191e13</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>1996</creationdate><topic>Bioconversions. Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>enantiospecificity</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>lipase</topic><topic>Methods. Procedures. Technologies</topic><topic>Steapsin</topic><topic>tetrahydropyran-2-methanol</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Kwatelai Quartey, E.G.</creatorcontrib><creatorcontrib>Hustad, Jan A.</creatorcontrib><creatorcontrib>Faber, Kurt</creatorcontrib><creatorcontrib>Anthonsen, Thorleif</creatorcontrib><collection>Pascal-Francis</collection><collection>CrossRef</collection><collection>Biotechnology Research Abstracts</collection><collection>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><jtitle>Enzyme and microbial technology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Kwatelai Quartey, E.G.</au><au>Hustad, Jan A.</au><au>Faber, Kurt</au><au>Anthonsen, Thorleif</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of tetrahydropyran-2-methanol</atitle><jtitle>Enzyme and microbial technology</jtitle><date>1996</date><risdate>1996</risdate><volume>19</volume><issue>5</issue><spage>361</spage><epage>366</epage><pages>361-366</pages><issn>0141-0229</issn><eissn>1879-0909</eissn><coden>EMTED2</coden><abstract>(±)-Tetrahydropyran-2-methanol (
1) was successfully resolved into both enantiomers on a preparative scale after optimization by hydrolysis of its butyrate ester (±)-
3 to (
R)-(−)-
3 (ee ⩾ 99%). The antipodal alcohol (
S)-(+)-
1 (ee ⩾ 95%) was obtained after recycling of the moderately
S-enriched
1 to the butyrate ester
3 and subsequent hydrolysis. A fourfold increase in enantioselectivity (
E value = 24) was observed when hydrolysis was performed using one of the fractions. Tetrahydrofurfuryl alcohol (
2) could not be resolved since the best selectivity attained was
E = 3.1 from hydrolysis by the lipase B of
Candida antarctica. Resolution by transesterification was found to be unsuitable for both compounds.</abstract><cop>Amsterdam</cop><pub>Elsevier Inc</pub><doi>10.1016/S0141-0229(96)00029-4</doi><tpages>6</tpages></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0141-0229 |
| ispartof | Enzyme and microbial technology, 1996, Vol.19 (5), p.361-366 |
| issn | 0141-0229 1879-0909 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_15778577 |
| source | Elsevier ScienceDirect Journals Complete |
| subjects | Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology enantiospecificity Fundamental and applied biological sciences. Psychology lipase Methods. Procedures. Technologies Steapsin tetrahydropyran-2-methanol |
| title | Selectivity enhancement of PPL-catalyzed resolution by enzyme fractionation and medium engineering: Syntheses of both enantiomers of tetrahydropyran-2-methanol |
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