Show simple item record

dc.contributor.authorSpeciale, G
dc.contributor.authorBernardi, A
dc.contributor.authorNisic, F
dc.date.accessioned2020-12-21T02:21:53Z
dc.date.available2020-12-21T02:21:53Z
dc.date.issued2013-07-24
dc.identifierpii: molecules18088779
dc.identifier.citationSpeciale, G., Bernardi, A. & Nisic, F. (2013). A facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl-glutamine building blocks.. Molecules, 18 (8), pp.8779-8785. https://doi.org/10.3390/molecules18088779.
dc.identifier.issn1420-3049
dc.identifier.urihttp://hdl.handle.net/11343/256895
dc.description.abstractAdenosine diphosphate ribosylation (ADP-ribosylation) is a widely occurring post-translational modification of proteins at nucleophilic side chain of amino acid residues. Elucidation of ADP-ribosylation events would benefit greatly from the availability of well-defined ADP-ribosylated peptides and analogues thereof. In this paper we present a novel approach to the chemical synthesis of ribosylated amino acid building blocks using traceless Staudinger ligation. We describe an efficient and stereoselective synthesis of α-N-ribosyl-asparagine (α-N-ribosyl-Asn) and α-N-ribosyl-glutamine (α-N-ribosyl-Gln) building blocks starting from 5-tert-butyldiphenylsilyl-β-D-ribofuranosyl azide. The N-glycosyl aminoacids are produced in good yields as pure α-anomers, suitably protected for peptide synthesis.
dc.languageeng
dc.publisherMDPI AG
dc.rights.urihttps://creativecommons.org/licenses/by/4.0
dc.titleA facile synthesis of α-N-ribosyl-asparagine and α-N-ribosyl-glutamine building blocks.
dc.typeJournal Article
dc.identifier.doi10.3390/molecules18088779
melbourne.affiliation.departmentSchool of Chemistry
melbourne.source.titleMolecules
melbourne.source.volume18
melbourne.source.issue8
melbourne.source.pages8779-8785
dc.rights.licenseCC BY
melbourne.elementsid1231280
melbourne.openaccess.pmchttp://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270248
melbourne.contributor.authorSPECIALE, GAETANO
dc.identifier.eissn1420-3049
melbourne.accessrightsOpen Access


Files in this item

Thumbnail

This item appears in the following Collection(s)

Show simple item record