Document Detail

Aqueous synthesis of peptide thioesters from amino acids and a thiol using 1,1'-carbonyldiimidazole.
MedLine Citation:
PMID:  16231206     Owner:  NLM     Status:  MEDLINE    
A new method was developed for the synthesis of peptide thioesters from free amino acids and thiols in water. This one-pot simple method involves two steps: (1) activation in water of an amino acid presumably as its N-carboxyanhydride (NCA) using 1,1'-carbonyldiimidazole (CDI), and (2) subsequent condensation of the activated amino acid-NCA in the presence of a thiol. With this method citrulline peptide thioesters containing up to 10 amino acid residues were prepared in a single reaction. This aqueous synthetic method provides a simple way to prepare peptide thioesters for studies of peptide replication involving ligation of peptide thioesters on peptide templates. The relevance of peptide replication to the origin-of-life process is supported by previous studies showing that amino acid thioesters (peptide thioester precursors) can be synthesized under prebiotic conditions by reaction of small sugars with ammonia and a thiol.
Arthur L Weber
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Publication Detail:
Type:  Comparative Study; Journal Article; Research Support, U.S. Gov't, Non-P.H.S.    
Journal Detail:
Title:  Origins of life and evolution of the biosphere : the journal of the International Society for the Study of the Origin of Life     Volume:  35     ISSN:  0169-6149     ISO Abbreviation:  Orig Life Evol Biosph     Publication Date:  2005 Oct 
Date Detail:
Created Date:  2005-10-18     Completed Date:  2006-10-05     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  8610391     Medline TA:  Orig Life Evol Biosph     Country:  Netherlands    
Other Details:
Languages:  eng     Pagination:  421-7     Citation Subset:  IM; S    
SETI Institute, Mail Stop 239-4, NASA Ames Research Center, Moffett Field, CA, 94035-1000, U.S.A.
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MeSH Terms
Amino Acids / chemistry*
Chromatography, High Pressure Liquid
Esters / chemical synthesis
Evolution, Chemical*
Imidazoles / chemistry*
Peptides / chemical synthesis*
Sulfhydryl Compounds / chemical synthesis*
Water / chemistry
Reg. No./Substance:
0/Amino Acids; 0/Esters; 0/Imidazoles; 0/Peptides; 0/Sulfhydryl Compounds; 530-62-1/N,N-carbonyldiimidazole; 7732-18-5/Water

From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine

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