| THAL, a sterically unhindered linker for the solid-phase synthesis of acid-sensitive protected peptide acids. | |
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MedLine Citation:
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PMID: 18722403 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The 5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol (THAL, Thiophene Acid Labile) is described as a new linker for the solid-phase synthesis of peptide carboxylic acids. It is based on the electron-rich 3,4-ethylenedioxythenyl (EDOTn) moiety and allows the obtention of free and tert-butyl-protected peptides by cleavage with 90% and 0.5% TFA, respectively. This very high acid lability makes it useful for the synthesis of sensitive peptides. Free and tert-butyl-protected Leu-enkephalins have been synthesized as models to demonstrate the utility of the linker. |
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Authors:
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Albert Isidro-Llobet; Ulrik Boas; Knud J Jensen; Mercedes Alvarez; Fernando Albericio |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-08-22 |
Journal Detail:
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Title: The Journal of organic chemistry Volume: 73 ISSN: 1520-6904 ISO Abbreviation: J. Org. Chem. Publication Date: 2008 Sep |
Date Detail:
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Created Date: 2008-09-15 Completed Date: 2008-11-14 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 2985193R Medline TA: J Org Chem Country: United States |
Other Details:
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Languages: eng Pagination: 7342-4 Citation Subset: IM |
Affiliation:
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Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Acids
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chemistry* Carboxylic Acids / chemical synthesis*, chemistry Crystallography, X-Ray Heterocyclic Compounds, 2-Ring / chemistry* Models, Molecular Molecular Structure Peptides / chemical synthesis*, chemistry Resins, Synthetic / chemical synthesis, chemistry Sensitivity and Specificity Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol; 0/Acids; 0/Carboxylic Acids; 0/Heterocyclic Compounds, 2-Ring; 0/Peptides; 0/Resins, Synthetic |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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