Document Detail

THAL, a sterically unhindered linker for the solid-phase synthesis of acid-sensitive protected peptide acids.
MedLine Citation:
PMID:  18722403     Owner:  NLM     Status:  MEDLINE    
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.
Albert Isidro-Llobet; Ulrik Boas; Knud J Jensen; Mercedes Alvarez; Fernando Albericio
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-08-22
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  73     ISSN:  1520-6904     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2008 Sep 
Date Detail:
Created Date:  2008-09-15     Completed Date:  2008-11-14     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  7342-4     Citation Subset:  IM    
Institute for Research in Biomedicine, Barcelona Science Park, University of Barcelona, Josep Samitier 1, 08028-Barcelona, Spain.
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MeSH Terms
Acids / 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
Reg. No./Substance:
0/5-(4-hydroxyphenyl)-3,4-ethylenedioxythienyl alcohol; 0/Acids; 0/Carboxylic Acids; 0/Heterocyclic Compounds, 2-Ring; 0/Peptides; 0/Resins, Synthetic

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