| Influence of extreme thermodynamic conditions and pyrite surfaces on peptide synthesis in aqueous media. | |
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MedLine Citation:
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PMID: 18254630 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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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. |
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Authors:
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Eduard Schreiner; Nisanth N Nair; Dominik Marx |
Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2008-02-07 |
Journal Detail:
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Title: Journal of the American Chemical Society Volume: 130 ISSN: 1520-5126 ISO Abbreviation: J. Am. Chem. Soc. Publication Date: 2008 Mar |
Date Detail:
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Created Date: 2008-02-27 Completed Date: 2008-04-15 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 7503056 Medline TA: J Am Chem Soc Country: United States |
Other Details:
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Languages: eng Pagination: 2768-70 Citation Subset: IM |
Affiliation:
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Lehrstuhl für Theoretische Chemie, Ruhr-Universität Bochum, 44780 Bochum, Germany. eduard.schreiner@theochem.rub.de |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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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:
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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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