| Copolymeric polythioesters by lipase-catalyzed thioesterification and transthioesterification of alpha,omega-alkanedithiols. | |
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MedLine Citation:
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PMID: 16007456 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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N Weber; K Bergander; E Fehling; E Klein; K Vosmann; K D Mukherjee |
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Publication Detail:
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Type: Journal Article Date: 2005-07-09 |
Journal Detail:
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Title: Applied microbiology and biotechnology Volume: 70 ISSN: 0175-7598 ISO Abbreviation: Appl. Microbiol. Biotechnol. Publication Date: 2006 Apr |
Date Detail:
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Created Date: 2006-03-07 Completed Date: 2006-06-22 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 8406612 Medline TA: Appl Microbiol Biotechnol Country: Germany |
Other Details:
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Languages: eng Pagination: 290-7 Citation Subset: IM |
Affiliation:
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Institute for Lipid Research, Federal Research Center for Nutrition and Food, Piusallee 68-76, 48147, Münster, Germany. niweber@uni-muenster.de |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkanes
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chemistry,
metabolism* Biotechnology / methods Enzymes, Immobilized Esterification Esters / chemistry, metabolism* Lipase / metabolism* Polymers / chemistry, metabolism Rhizomucor / enzymology Sulfhydryl Compounds / chemistry, metabolism* |
| Chemical | |
Reg. No./Substance:
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0/Alkanes; 0/Enzymes, Immobilized; 0/Esters; 0/Polymers; 0/Sulfhydryl Compounds; EC 3.1.1.-/Lipozyme; EC 3.1.1.3/Lipase |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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