| Proton affinity of canavanine and canaline, oxyanalogues of arginine and ornithine, from the extended kinetic method. | |
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MedLine Citation:
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PMID: 17020263 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The absolute proton affinities of the nonprotein amino acids canavanine and canaline have been determined using the extended kinetic method in an electrospray ionization quadrupole ion trap instrument. Canavanine results from the substitution of an oxygen atom for the delta-CH2 group in the side chain of the protein amino acid arginine, whereas canaline results from a similar substitution at the delta-CH2 group in the side chain of ornithine. Absolute proton affinities of 1001+/-9 and 950+/-7 kJ/mol are obtained for canavanine and canaline, respectively. For canaline, this proton affinity is in excellent agreement with theoretical predictions obtained using the hybrid density functional theory method B3LYP/6-311++G**//B3LYP/6-31+G*. For canavanine, theory predicts a somewhat larger proton affinity of 1015 kJ/mol. Oxygen atom substitution in these nonprotein amino acids results in a decrease in their proton affinities of 40-50 kJ/mol compared to arginine and ornithine. |
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Authors:
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Erica J Andriole; Kathryn E Colyer; Elizabeth Cornell; John C Poutsma |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't; Research Support, U.S. Gov't, Non-P.H.S. |
Journal Detail:
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Title: The journal of physical chemistry. A Volume: 110 ISSN: 1089-5639 ISO Abbreviation: J Phys Chem A Publication Date: 2006 Oct |
Date Detail:
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Created Date: 2006-10-05 Completed Date: 2007-09-13 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9890903 Medline TA: J Phys Chem A Country: United States |
Other Details:
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Languages: eng Pagination: 11501-8 Citation Subset: IM |
Affiliation:
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Department of Chemistry, The College of William and Mary, Williamsburg, Virginia 23187-8795, USA. |
Export Citation:
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APA/MLA Format Download EndNote Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Aminobutyric Acids
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chemistry* Arginine / analogs & derivatives*, chemistry Canavanine / chemistry* Computer Simulation Kinetics Models, Molecular Molecular Structure Ornithine / analogs & derivatives*, chemistry Oxygen / chemistry* Protons* Thermodynamics |
| Chemical | |
Reg. No./Substance:
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0/Aminobutyric Acids; 0/Protons; 496-93-5/canaline; 543-38-4/Canavanine; 7006-33-9/Ornithine; 74-79-3/Arginine; 7782-44-7/Oxygen |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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