| Efficient protocols for the synthesis of enantiopure gamma-amino acids with proteinogenic side chains. | |
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MedLine Citation:
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PMID: 12803497 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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The synthesis of enantiopure gamma-substituted gamma-amino acids with proteinogenic side chains, starting from the corresponding natural alpha-amino acids, was studied. N-Protected amino aldehydes containing various protective groups were prepared from the corresponding amino alcohols by oxidation with NaOCl in the presence of AcNH-TEMPO and directly reacted with methyl, benzyl and tert-butyl phosphoranylidene acetate to produce alpha,beta-unsaturated gamma-amino esters. Simultaneous hydrogenation of the double bond and removal of either the benzyl or benzyloxycarbonyl group led to N- or C-protected gamma-amino acids in high yield. The enantiomeric purity was studied by 1H NMR analysis of Mosher amides and chiral HPLC analysis. |
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Authors:
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Vassilios Loukas; Caterina Noula; George Kokotos |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't |
Journal Detail:
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Title: Journal of peptide science : an official publication of the European Peptide Society Volume: 9 ISSN: 1075-2617 ISO Abbreviation: J. Pept. Sci. Publication Date: 2003 May |
Date Detail:
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Created Date: 2003-06-13 Completed Date: 2004-01-13 Revised Date: 2006-11-15 |
Medline Journal Info:
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Nlm Unique ID: 9506309 Medline TA: J Pept Sci Country: England |
Other Details:
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Languages: eng Pagination: 312-9 Citation Subset: IM |
Affiliation:
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Laboratory of Organic Chemistry, Department of Chemistry, University of Athens, Panepistimiopolis, Athens 15771, Greece. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Aldehydes
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chemistry Amino Acids / chemical synthesis*, chemistry Amino Alcohols / chemistry Chromatography, High Pressure Liquid / methods Hydrogenation Magnetic Resonance Spectroscopy Oxidation-Reduction Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Aldehydes; 0/Amino Acids; 0/Amino Alcohols |
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