A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids

DSpace/Manakin Repository

Show simple item record

dc.contributor.author O'Reilly, Elaine
dc.contributor.author Balducci, Daniele
dc.contributor.author Paradisi, Francesca
dc.date.accessioned 2012-06-13T15:39:44Z
dc.date.available 2012-06-13T15:39:44Z
dc.date.copyright 2010 Springer en
dc.date.issued 2010
dc.identifier.citation Amino Acids en
dc.identifier.uri http://hdl.handle.net/10197/3640
dc.description.abstract An atom-efficient and stereoselective synthesis has been developed for the preparation of a-2H-labelled(S)-a-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 a-amino acids. en
dc.description.sponsorship Higher Education Authority en
dc.description.sponsorship Irish Research Council for Science, Engineering and Technology en
dc.format.extent 362496 bytes
dc.format.mimetype application/msword
dc.language.iso en en
dc.publisher Springer en
dc.rights The final publication is available at springerlink.com en
dc.subject (S)-Deuterated-alpha-amino acids en
dc.subject diketopiperazine en
dc.subject Asymmetric synthesis en
dc.subject.lcsh Amino acids--Synthesis en
dc.subject.lcsh Organic cyclic compounds en
dc.subject.lcsh Asymmetric synthesis en
dc.title A stereoselective synthesis of α-deuterium labelled (S)-α-amino acids en
dc.type Journal Article en
dc.internal.availability Full text available en
dc.status Peer reviewed en
dc.identifier.volume 39 en
dc.identifier.issue 3 en
dc.identifier.startpage 849 en
dc.identifier.endpage 858 en
dc.identifier.doi 10.1007/s00726-010-0541-3
dc.neeo.contributor O'Reilly|Elaine|aut| en
dc.neeo.contributor Balducci|Daniele|aut| en
dc.neeo.contributor Paradisi|Francesca|aut| en


Files in this item

This item appears in the following Collection(s)

Show simple item record

This item is available under the Attribution-NonCommercial-NoDerivs 3.0 Ireland. No item may be reproduced for commercial purposes. For other possible restrictions on use please refer to the publisher's URL where this is made available, or to notes contained in the item itself. Other terms may apply.

If you are a publisher or author and have copyright concerns for any item, please email research.repository@ucd.ie and the item will be withdrawn immediately. The author or person responsible for depositing the article will be contacted within one business day.

Search Research Repository


Advanced Search

Browse