| A stereoselective synthesis of alpha-deuterium-labelled (S)-alpha-amino acids. | |
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MedLine Citation:
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PMID: 20225136 Owner: NLM Status: MEDLINE |
Abstract/OtherAbstract:
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An atom-efficient and stereoselective synthesis has been developed for the preparation of alpha-2H-labelled (S)-alpha-amino acids, starting from a novel chiral diketopiperazine scaffold. Efficient mono-alkylation of the chiral template afforded the (S)-substituted adducts with the nature of the electrophile significantly effecting the stereochemical outcome. Subsequent alkylation was totally selective producing the 1,4-cis adduct as the sole diastereoisomer. The deprotection was carried out using cerium ammonium nitrate followed by acid hydrolysis affording the enantipure alpha-amino acids. |
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Authors:
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Elaine O'Reilly; Daniele Balducci; Francesca Paradisi |
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Publication Detail:
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Type: Journal Article; Research Support, Non-U.S. Gov't Date: 2010-03-12 |
Journal Detail:
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Title: Amino acids Volume: 39 ISSN: 1438-2199 ISO Abbreviation: Amino Acids Publication Date: 2010 Aug |
Date Detail:
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Created Date: 2010-07-23 Completed Date: 2010-10-28 Revised Date: - |
Medline Journal Info:
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Nlm Unique ID: 9200312 Medline TA: Amino Acids Country: Austria |
Other Details:
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Languages: eng Pagination: 849-58 Citation Subset: IM |
Affiliation:
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UCD School of Chemistry and Chemical Biology, Centre for Synthesis and Chemical Biology, Belfield, Dublin 4, Ireland. |
Export Citation:
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| MeSH Terms | |
Descriptor/Qualifier:
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Alkylation Amino Acids / chemical synthesis, chemistry* Deuterium / chemistry* Diketopiperazines / chemistry Hydrolysis Isotope Labeling Stereoisomerism |
| Chemical | |
Reg. No./Substance:
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0/Amino Acids; 0/Diketopiperazines; 7782-39-0/Deuterium |
From MEDLINE®/PubMed®, a database of the U.S. National Library of Medicine
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