Document Detail

Comparative evaluation of four trityl-type amidomethyl polystyrene resins in Fmoc solid phase peptide synthesis.
MedLine Citation:
PMID:  12916639     Owner:  NLM     Status:  MEDLINE    
Four trityl-type (i.e. non-substituted trityl-, o-Cl-trityl-, o-F-trityl- and p-CN-trityl-) amidomethyl polystyrene resins were evaluated comparatively, in terms of the stability of the trityl-ester bond in slightly acidic dichloromethane solutions, and the p-CN-trityl-amidomethyl polystyrene resin was found to be the most stable of them. The above resins were applied, in parallel with Wang benzyl-type resin, well known for its stability in mild acidic conditions, to the Fmoc solid phase synthesis of the 43-amino acid residue long bioactive peptide thymosin beta-4. Independent of their differences in acid sensitivity, the resins seemed to function equally well under the conditions used, since pure thymosin beta-4 was obtained with a final yield of approximately 30% from each resin. The trityl-type amidomethyl polystyrene resins were also applied, in parallel with the Wang resin, to the Fmoc solid phase synthesis of a bioactive peptide containing proline at its C-terminus, i.e. the N-terminal tetrapeptide of thymosin beta-4, AcSDKP. In this case, the best yield (87%) was obtained with the o-Cl-trityl-amidomethyl polystyrene resin, which may be the resin of choice, of those studied, for the Fmoc solid phase peptide synthesis.
Christos Zikos; Evangelia Livaniou; Leondios Leondiadis; Nikolas Ferderigos; Dionyssis S Ithakissios; Gregory P Evangelatos
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Publication Detail:
Type:  Comparative Study; Journal Article    
Journal Detail:
Title:  Journal of peptide science : an official publication of the European Peptide Society     Volume:  9     ISSN:  1075-2617     ISO Abbreviation:  J. Pept. Sci.     Publication Date:  2003 Jul 
Date Detail:
Created Date:  2003-08-14     Completed Date:  2004-04-02     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  9506309     Medline TA:  J Pept Sci     Country:  England    
Other Details:
Languages:  eng     Pagination:  419-29     Citation Subset:  IM    
Institute of Radioisotopes and Radiodiagnostic Products, National Center for Scientific Research Demokritos, Athens, Greece.
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MeSH Terms
Molecular Structure
Oligopeptides / chemical synthesis*
Polystyrenes / chemistry*
Resins, Synthetic / chemistry*
Reg. No./Substance:
0/Oligopeptides; 0/Polystyrenes; 0/Resins, Synthetic

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