Document Detail


Influence of extreme thermodynamic conditions and pyrite surfaces on peptide synthesis in aqueous media.
MedLine Citation:
PMID:  18254630     Owner:  NLM     Status:  MEDLINE    
Abstract/OtherAbstract:
Free energy landscapes and reaction mechanisms underlying the synthesis of diglycine in water were studied computationally. It was found that amino acid activation by carbonyl sulfide, leading to the formation of a cyclic alpha-amino acid N-carboxyanhydride (NCA, or Leuchs anhydride), preferentially follows an indirect pathway that involves an isocyanate intermediate. Extreme temperature and pressure conditions accelerate peptidization greatly compared to the ambient bulk water environment and are shown to favor, in general, concerted versus stepwise mechanisms. Finally, a pyrite surface, FeS2 (001), is found to lower reaction barriers further by decreasing fluctuations and by assisting the preformation of the cyclic five-membered NCA ring due to scaffolding.
Authors:
Eduard Schreiner; Nisanth N Nair; Dominik Marx
Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't     Date:  2008-02-07
Journal Detail:
Title:  Journal of the American Chemical Society     Volume:  130     ISSN:  1520-5126     ISO Abbreviation:  J. Am. Chem. Soc.     Publication Date:  2008 Mar 
Date Detail:
Created Date:  2008-02-27     Completed Date:  2008-04-15     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  7503056     Medline TA:  J Am Chem Soc     Country:  United States    
Other Details:
Languages:  eng     Pagination:  2768-70     Citation Subset:  IM    
Affiliation:
Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum, Germany. eduard.schreiner@theochem.rub.de
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MeSH Terms
Descriptor/Qualifier:
Computer Simulation
Cyclization
Glycylglycine / chemical synthesis*,  chemistry
Iron / chemistry*
Models, Chemical
Peptides / chemical synthesis*,  chemistry
Pressure
Sulfides / chemistry*
Surface Properties
Thermodynamics*
Water / chemistry
Chemical
Reg. No./Substance:
0/Peptides; 0/Sulfides; 1309-36-0/pyrite; 556-50-3/Glycylglycine; 7439-89-6/Iron; 7732-18-5/Water

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


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