| Cyclic forms of the alpha-keto acid analogs of arginine, citrulline, homoarginine, and homocitrulline. | |
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MedLine Citation:
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PMID:Â 670205 Â Â Â Owner:Â NLM Â Â Â Status:Â MEDLINE Â Â Â |
Abstract/OtherAbstract:
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The alpha-keto acid analogs of arginine and citrulline (and of their next higher homologs, homoarginine and homocitrulline) were prepared enzymatically and shown to exist in equilibrium with cyclic forms which predominate in solution and in the solid state. The cyclic forms of the alpha-keto acid analogs of arginine and homoarginine have the structures pyrrolidine-1-amidino-2-hydroxy-2-carboxylic acid and piperidine-1-amidino-2-hydroxy-2-carboxylic acid, respectively. The cyclic forms of the alpha-keto acid analogs of citrulline and homocitrulline have the structures pyrrolidine-1-carbamyl-2-hydroxy-2-carboxylic acid and piperidine-1-carbamyl-2-carboxylic acid, respectively. The latter compound can undergo further cyclization and dehydration to form additional products, whose structures (2H, 5H, 7H-imidazo[1,5-a]pyridine-1,3-dione and 2H, 5H, 7H, 9H-9-hydroxy-imidazo[1,5-a]pyridine-1,3-dione) were deduced. The alpha-keto acids investigated here, which may be formed reversibly by enzymatic transamination of the corresponding amino acids, may be formed in vivo especially in the presence of metabolic abnormalities associated with inborn enzymatic defects. |
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Authors:
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A J Cooper; A Meister |
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Publication Detail:
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Type:Â Journal Article; Research Support, U.S. Gov't, P.H.S. Â Â Â |
Journal Detail:
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Title: The Journal of biological chemistry    Volume: 253    ISSN: 0021-9258    ISO Abbreviation: J. Biol. Chem.    Publication Date: 1978 Aug |
Date Detail:
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Created Date:Â 1978-09-15 Â Â Â Completed Date:Â 1978-09-15 Â Â Â Revised Date:Â 2006-11-15 Â Â Â |
Medline Journal Info:
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Nlm Unique ID: 2985121R    Medline TA: J Biol Chem    Country: UNITED STATES    |
Other Details:
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Languages: eng    Pagination: 5407-10    Citation Subset: IM    |
Export Citation:
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APA/MLA Format    Download EndNote    Download BibTex |
| MeSH Terms | |
Descriptor/Qualifier:
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Arginine
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analogs & derivatives* Citrulline / analogs & derivatives* Homoarginine / analogs & derivatives* Imino Acids* Keto Acids Kinetics Magnetic Resonance Spectroscopy Molecular Conformation Oxidation-Reduction Spectrophotometry Structure-Activity Relationship |
| Chemical | |
Reg. No./Substance:
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0/Imino Acids; 0/Keto Acids; 156-86-5/Homoarginine; 372-75-8/Citrulline; 74-79-3/Arginine |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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