Document Detail


Development of a new microwave-assisted cleavable backbone amide linker (BAL): a comparative study.
MedLine Citation:
PMID:  20024133     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
A thorough comparative study to demonstrate the properties of a new microwave labile backbone amide linker is presented. A cyclic pentapeptide, cyclo(Trp-Gln-Gly-beta-Ala-Phe), was used as a model and synthesized following 16 different conditions. The new backbone amide linker is stable towards acid and base at r.t., and can be cleaved at elevated temperature in trifluoroacetic acid under microwave irradiation, avoiding the use of aggressive reagents like HF. The new linker is compatible with Boc- as well as Fmoc-strategy and allows the cleavage of acid labile side chain protective groups at r.t., prior to cleavage of the cyclic pentapeptide from the resin.
Authors:
Stijn Claerhout; Thibault Duch?ne; Dirk Tourw?; Erik V Van der Eycken
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, Non-U.S. Gov't     Date:  2009-11-19
Journal Detail:
Title:  Organic & biomolecular chemistry     Volume:  8     ISSN:  1477-0539     ISO Abbreviation:  Org. Biomol. Chem.     Publication Date:  2010 Jan 
Date Detail:
Created Date:  2009-12-23     Completed Date:  2010-03-23     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  101154995     Medline TA:  Org Biomol Chem     Country:  England    
Other Details:
Languages:  eng     Pagination:  60-5     Citation Subset:  IM    
Affiliation:
Laboratory for Organic and Microwave-Assisted Chemistry (LOMAC), Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, B-3001 Leuven, Belgium.
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MeSH Terms
Descriptor/Qualifier:
Amides / chemistry*
Amino Acid Sequence
Microwaves
Molecular Structure
Peptides, Cyclic / chemical synthesis*,  chemistry
Chemical
Reg. No./Substance:
0/Amides; 0/Peptides, Cyclic

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