Show simple item record

dc.contributor.authorFox, Karen A.
dc.contributor.authorChadda, Rekha
dc.contributor.authorCardona, Francisco
dc.contributor.authorBarron, Stephen
dc.contributor.authorMcArdle, Patrick
dc.contributor.authorMurphy, Paul V.
dc.date.accessioned2021-01-08T11:30:33Z
dc.date.available2021-01-08T11:30:33Z
dc.date.issued2020-09-18
dc.identifier.citationFox, Karen A., Chadda, Rekha, Cardona, Francisco, Barron, Stephen, McArdle, Patrick, & Murphy, Paul V. (2020). Building blocks from monosaccharides for synthesis of scaffolds, including macrocycles. Application of allylic azide rearrangement, azide-alkyne cycloaddition and ring closing metathesis. Tetrahedron, 76(45), 131495. doi:https://doi.org/10.1016/j.tet.2020.131495en_IE
dc.identifier.issn0040-4020
dc.identifier.urihttp://hdl.handle.net/10379/16436
dc.description.abstractSynthesis of compounds with characteristics of natural products are required to increase the diversity and biological relevance of compounds for screening. These include new frameworks/scaffolds, with multiple stereogenic centres and various functional groups. Carbohydrates are renewable, readily available and have stereochemical diversity and functionality. Herein, building blocks derived from monosaccharides with alkene, alkyne and organic azide functional groups are used. The build-couple-pair strategy of diversity oriented synthesis is employed taking advantage of RuAAC, CuAAC and thermally promoted azide-alkyne cycloadditions, allylic azide (Winstein) rearrangement and ring closing metathesis, leading to polyhydroxylated small, medium and macrocyclic ring containing scaffolds. There is potential to graft appendages (e.g. pharmacophoric groups) to further increase diversity of compounds available for screening, or to consider the scaffolds in ligand design.en_IE
dc.description.sponsorshipRC and KF thank NUI Galway’s College of Science for scholarships. A proportion of the material presented herein was funded by Science Foundation Ireland (13/TIDA/B2651) co-funded by the European Regional Development Fund.en_IE
dc.formatapplication/pdfen_IE
dc.language.isoenen_IE
dc.publisherElsevieren_IE
dc.relation.ispartofTetrahedronen
dc.subjectMacrocycleen_IE
dc.subjectCycloadditionen_IE
dc.subjectMonosaccharideen_IE
dc.subjectScaffolden_IE
dc.subjectAllylic azide rearrangementen_IE
dc.subjectMedium ringen_IE
dc.titleBuilding blocks from monosaccharides for synthesis of scaffolds, including macrocycles. Application of allylic azide rearrangement, azide-alkyne cycloaddition and ring closing metathesisen_IE
dc.typeArticleen_IE
dc.date.updated2021-01-07T08:39:29Z
dc.identifier.doi10.1016/j.tet.2020.131495
dc.local.publishedsourcehttps://doi.org/10.1016/j.tet.2020.131495en_IE
dc.description.peer-reviewedpeer-reviewed
dc.contributor.funderCollege of Science, National University of Ireland, Galwayen_IE
dc.contributor.funderScience Foundation Irelanden_IE
dc.contributor.funderEuropean Regional Development Funden_IE
dc.internal.rssid24261657
dc.local.contactPaul Murphy, School Of Chemistry, Room 108, Arts/Science Building, Nui Galway. 2465 Email: paul.v.murphy@nuigalway.ie
dc.local.copyrightcheckedYes
dc.local.versionACCEPTED
dcterms.projectinfo:eu-repo/grantAgreement/SFI/SFI Technology and Innovation Development Award (TIDA)/13/TIDA/B2651/IE/Divergent synthesis of proprietary macrocyclic scaffolds and libraries for screening/en_IE
nui.item.downloads89


Files in this item

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

The following license files are associated with this item:

Thumbnail

This item appears in the following Collection(s)

Show simple item record