Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of α,ω-alkanedithiols
Linear copolymeric polythioesters [PTE; poly(alpha,omega-alkanedioic acid-co-alpha,omega-alkanedithiols)] were formed in good yield (approximately 69%) by thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol and 1,8-octanedithiol, respectively, catalyzed by immobilized lipase from Rh...
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| Veröffentlicht in: | Applied microbiology and biotechnology 2006-04, Vol.70 (3), p.290-297 |
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| creator | WEBER, N BERGANDER, K FEHLING, E KLEIN, E VOSMANN, K MUKHERJEE, K. D |
| description | Linear copolymeric polythioesters [PTE; poly(alpha,omega-alkanedioic acid-co-alpha,omega-alkanedithiols)] were formed in good yield (approximately 69%) by thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol and 1,8-octanedithiol, respectively, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo without a solvent. Similarly, transthioesterification (thiolysis) of diethyl 1,12-dodecanedioate with 1,6-hexanedithiol led to the formation of approximately 66% PTE. Poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) and poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) were extracted from the reaction mixture using methyl-t-butylether, precipitated at -20 degrees C and the precipitates extracted with boiling i-hexane to yield two fractions of PTE. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) shows an average molecular mass (Mw) of 1,212 Da, corresponding to a molecular weight range of up to 13,200 Da and a degree of polymerization of up to 38 monomer units. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) shows a Mw of 2,360 Da, corresponding to a molecular weight range of up to 19,500 Da and a maximum degree of polymerization of up to 52 monomer units. The low-molecular weight ( |
| doi_str_mv | 10.1007/s00253-005-027-5 |
| format | Article |
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D</creator><creatorcontrib>WEBER, N ; BERGANDER, K ; FEHLING, E ; KLEIN, E ; VOSMANN, K ; MUKHERJEE, K. D</creatorcontrib><description>Linear copolymeric polythioesters [PTE; poly(alpha,omega-alkanedioic acid-co-alpha,omega-alkanedithiols)] were formed in good yield (approximately 69%) by thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol and 1,8-octanedithiol, respectively, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo without a solvent. Similarly, transthioesterification (thiolysis) of diethyl 1,12-dodecanedioate with 1,6-hexanedithiol led to the formation of approximately 66% PTE. Poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) and poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) were extracted from the reaction mixture using methyl-t-butylether, precipitated at -20 degrees C and the precipitates extracted with boiling i-hexane to yield two fractions of PTE. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) shows an average molecular mass (Mw) of 1,212 Da, corresponding to a molecular weight range of up to 13,200 Da and a degree of polymerization of up to 38 monomer units. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) shows a Mw of 2,360 Da, corresponding to a molecular weight range of up to 19,500 Da and a maximum degree of polymerization of up to 52 monomer units. The low-molecular weight (<800 Da) reaction products of thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol, elucidated by gas chromatography-mass spectroscopy, show the following intermediates: (1) 9,20-dioxo-1,8-dithiacycloeicosane; (2) 17,28-dioxo-1,8,9,16-tetrathiacyclooctacosane; (3) 1,12-dodecanedioic acid methyl(O)ester 6'-S-mercaptohexyl thio(S)ester; and (4) oligomeric linear thioester, formed by thioesterification of two molecules of 1,12-dodecanedioic acid with one molecule of 1,6-hexanedithiol.</description><identifier>ISSN: 0175-7598</identifier><identifier>EISSN: 1432-0614</identifier><identifier>DOI: 10.1007/s00253-005-027-5</identifier><identifier>PMID: 16007456</identifier><identifier>CODEN: AMBIDG</identifier><language>eng</language><publisher>Berlin: Springer</publisher><subject>Alkanes - chemistry ; Alkanes - metabolism ; Bioconversions. Hemisynthesis ; Biological and medical sciences ; Biotechnology ; Biotechnology - methods ; Enzymes, Immobilized ; Esterification ; Esters - chemistry ; Esters - metabolism ; Fundamental and applied biological sciences. Psychology ; Lipase - metabolism ; Methods. Procedures. Technologies ; Polymers - chemistry ; Polymers - metabolism ; Rhizomucor - enzymology ; Rhizomucor miehei ; Sulfhydryl Compounds - chemistry ; Sulfhydryl Compounds - metabolism</subject><ispartof>Applied microbiology and biotechnology, 2006-04, Vol.70 (3), p.290-297</ispartof><rights>2006 INIST-CNRS</rights><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c358t-33c3bf05b38aae9853ce72e1b8a6a910d7781038350756949772592bb327519b3</citedby><cites>FETCH-LOGICAL-c358t-33c3bf05b38aae9853ce72e1b8a6a910d7781038350756949772592bb327519b3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids><backlink>$$Uhttp://pascal-francis.inist.fr/vibad/index.php?action=getRecordDetail&idt=17629276$$DView record in Pascal Francis$$Hfree_for_read</backlink><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/16007456$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>WEBER, N</creatorcontrib><creatorcontrib>BERGANDER, K</creatorcontrib><creatorcontrib>FEHLING, E</creatorcontrib><creatorcontrib>KLEIN, E</creatorcontrib><creatorcontrib>VOSMANN, K</creatorcontrib><creatorcontrib>MUKHERJEE, K. D</creatorcontrib><title>Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of α,ω-alkanedithiols</title><title>Applied microbiology and biotechnology</title><addtitle>Appl Microbiol Biotechnol</addtitle><description>Linear copolymeric polythioesters [PTE; poly(alpha,omega-alkanedioic acid-co-alpha,omega-alkanedithiols)] were formed in good yield (approximately 69%) by thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol and 1,8-octanedithiol, respectively, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo without a solvent. Similarly, transthioesterification (thiolysis) of diethyl 1,12-dodecanedioate with 1,6-hexanedithiol led to the formation of approximately 66% PTE. Poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) and poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) were extracted from the reaction mixture using methyl-t-butylether, precipitated at -20 degrees C and the precipitates extracted with boiling i-hexane to yield two fractions of PTE. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) shows an average molecular mass (Mw) of 1,212 Da, corresponding to a molecular weight range of up to 13,200 Da and a degree of polymerization of up to 38 monomer units. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) shows a Mw of 2,360 Da, corresponding to a molecular weight range of up to 19,500 Da and a maximum degree of polymerization of up to 52 monomer units. The low-molecular weight (<800 Da) reaction products of thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol, elucidated by gas chromatography-mass spectroscopy, show the following intermediates: (1) 9,20-dioxo-1,8-dithiacycloeicosane; (2) 17,28-dioxo-1,8,9,16-tetrathiacyclooctacosane; (3) 1,12-dodecanedioic acid methyl(O)ester 6'-S-mercaptohexyl thio(S)ester; and (4) oligomeric linear thioester, formed by thioesterification of two molecules of 1,12-dodecanedioic acid with one molecule of 1,6-hexanedithiol.</description><subject>Alkanes - chemistry</subject><subject>Alkanes - metabolism</subject><subject>Bioconversions. Hemisynthesis</subject><subject>Biological and medical sciences</subject><subject>Biotechnology</subject><subject>Biotechnology - methods</subject><subject>Enzymes, Immobilized</subject><subject>Esterification</subject><subject>Esters - chemistry</subject><subject>Esters - metabolism</subject><subject>Fundamental and applied biological sciences. Psychology</subject><subject>Lipase - metabolism</subject><subject>Methods. Procedures. Technologies</subject><subject>Polymers - chemistry</subject><subject>Polymers - metabolism</subject><subject>Rhizomucor - enzymology</subject><subject>Rhizomucor miehei</subject><subject>Sulfhydryl Compounds - chemistry</subject><subject>Sulfhydryl Compounds - metabolism</subject><issn>0175-7598</issn><issn>1432-0614</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2006</creationdate><recordtype>article</recordtype><sourceid>EIF</sourceid><recordid>eNqFkTtOAzEQhi0EIiHQU6FtoMIwttevEkW8pEg0UFter1cYnGxYZ4twA47DReBKOEpEGiQqWzPfPxrNh9AxgQsCIC8TAOUMA3AMVGK-g4akZBSDIOUuGgKRHEuu1QAdpPQCQKgSYh8NiMjpkosh6sftvI3Lqe-CK1a_xXNofVr4LhXVsohhbpPHzi5sXL77uvhthybkamhnhZ3lcmdn6Y9e2xRfn-ffH9jGVzvzdVgxMR2ivcbG5I827wg93Vw_ju_w5OH2fnw1wY5xtcCMOVY1wCumrPVacea8pJ5UygqrCdRSKgJMMQ6SC11qKSnXtKoYlZzoio3Q2XruvGvf-rybmYbkfIx5l7ZPRuQAA0H_BYmmWiuQGYQ16Lo2pc43Zt6Fqe2WhoBZOTFrJyY7MdmJ4TlyspndV1NfbwMbCRk43QA2ORubfEsX0paTgmoqBfsBoa6XZw</recordid><startdate>20060401</startdate><enddate>20060401</enddate><creator>WEBER, N</creator><creator>BERGANDER, K</creator><creator>FEHLING, E</creator><creator>KLEIN, E</creator><creator>VOSMANN, K</creator><creator>MUKHERJEE, K. 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Hemisynthesis</topic><topic>Biological and medical sciences</topic><topic>Biotechnology</topic><topic>Biotechnology - methods</topic><topic>Enzymes, Immobilized</topic><topic>Esterification</topic><topic>Esters - chemistry</topic><topic>Esters - metabolism</topic><topic>Fundamental and applied biological sciences. Psychology</topic><topic>Lipase - metabolism</topic><topic>Methods. Procedures. Technologies</topic><topic>Polymers - chemistry</topic><topic>Polymers - metabolism</topic><topic>Rhizomucor - enzymology</topic><topic>Rhizomucor miehei</topic><topic>Sulfhydryl Compounds - chemistry</topic><topic>Sulfhydryl Compounds - metabolism</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>WEBER, N</creatorcontrib><creatorcontrib>BERGANDER, K</creatorcontrib><creatorcontrib>FEHLING, E</creatorcontrib><creatorcontrib>KLEIN, E</creatorcontrib><creatorcontrib>VOSMANN, K</creatorcontrib><creatorcontrib>MUKHERJEE, K. D</creatorcontrib><collection>Pascal-Francis</collection><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>Technology Research Database</collection><collection>Engineering Research Database</collection><collection>Biotechnology and BioEngineering Abstracts</collection><collection>MEDLINE - Academic</collection><jtitle>Applied microbiology and biotechnology</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>WEBER, N</au><au>BERGANDER, K</au><au>FEHLING, E</au><au>KLEIN, E</au><au>VOSMANN, K</au><au>MUKHERJEE, K. D</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of α,ω-alkanedithiols</atitle><jtitle>Applied microbiology and biotechnology</jtitle><addtitle>Appl Microbiol Biotechnol</addtitle><date>2006-04-01</date><risdate>2006</risdate><volume>70</volume><issue>3</issue><spage>290</spage><epage>297</epage><pages>290-297</pages><issn>0175-7598</issn><eissn>1432-0614</eissn><coden>AMBIDG</coden><abstract>Linear copolymeric polythioesters [PTE; poly(alpha,omega-alkanedioic acid-co-alpha,omega-alkanedithiols)] were formed in good yield (approximately 69%) by thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol and 1,8-octanedithiol, respectively, catalyzed by immobilized lipase from Rhizomucor miehei (Lipozyme RM IM) in vacuo without a solvent. Similarly, transthioesterification (thiolysis) of diethyl 1,12-dodecanedioate with 1,6-hexanedithiol led to the formation of approximately 66% PTE. Poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) and poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) were extracted from the reaction mixture using methyl-t-butylether, precipitated at -20 degrees C and the precipitates extracted with boiling i-hexane to yield two fractions of PTE. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,6-hexanedithiol) shows an average molecular mass (Mw) of 1,212 Da, corresponding to a molecular weight range of up to 13,200 Da and a degree of polymerization of up to 38 monomer units. The i-hexane-insoluble fraction of poly (1,12-dodecanedioic acid-co-1,8-octanedithiol) shows a Mw of 2,360 Da, corresponding to a molecular weight range of up to 19,500 Da and a maximum degree of polymerization of up to 52 monomer units. The low-molecular weight (<800 Da) reaction products of thioesterification of 1,12-dodecanedioic acid with 1,6-hexanedithiol, elucidated by gas chromatography-mass spectroscopy, show the following intermediates: (1) 9,20-dioxo-1,8-dithiacycloeicosane; (2) 17,28-dioxo-1,8,9,16-tetrathiacyclooctacosane; (3) 1,12-dodecanedioic acid methyl(O)ester 6'-S-mercaptohexyl thio(S)ester; and (4) oligomeric linear thioester, formed by thioesterification of two molecules of 1,12-dodecanedioic acid with one molecule of 1,6-hexanedithiol.</abstract><cop>Berlin</cop><pub>Springer</pub><pmid>16007456</pmid><doi>10.1007/s00253-005-027-5</doi><tpages>8</tpages></addata></record> |
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| subjects | Alkanes - chemistry Alkanes - metabolism Bioconversions. Hemisynthesis Biological and medical sciences Biotechnology Biotechnology - methods Enzymes, Immobilized Esterification Esters - chemistry Esters - metabolism Fundamental and applied biological sciences. Psychology Lipase - metabolism Methods. Procedures. Technologies Polymers - chemistry Polymers - metabolism Rhizomucor - enzymology Rhizomucor miehei Sulfhydryl Compounds - chemistry Sulfhydryl Compounds - metabolism |
| title | Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of α,ω-alkanedithiols |
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