Please use this identifier to cite or link to this item:
https://hdl.handle.net/1959.11/20308
Full metadata record
DC Field | Value | Language |
---|---|---|
dc.contributor.author | Wilkinson, Brendan | en |
dc.contributor.author | Chun, Candy K Y | en |
dc.contributor.author | Payne, Richard J | en |
dc.date.accessioned | 2017-03-31T15:56:00Z | - |
dc.date.issued | 2011 | - |
dc.identifier.citation | Biopolymers, 96(2), p. 137-146 | en |
dc.identifier.issn | 1097-0282 | en |
dc.identifier.issn | 0006-3525 | en |
dc.identifier.uri | https://hdl.handle.net/1959.11/20308 | - |
dc.description.abstract | MUC1 is a cell-surface, epithelial glycoprotein that forms an essential protective barrier of cells and serves to modulate intercellular communication. During cancer progression, the dysregulation of glycosyltransferases, which serve to elongate cell-surface glycans, leads to aberrant glycosylation patterns on this glycoprotein. This results in the presentation of well-characterized, tumorassociated carbohydrate antigens (TACAs) which represent important biomarkers for a range of epithelial cancers. The synthesis of well-defined, multivalent MUC1 glycopeptide constructs bearing TACAs therefore represents a viable opportunity for the development of cancer vaccine candidates. We report herein the synthesis of a glycopeptide thioester, comprising the full eicosapeptide variable number tandem repeat (VNTR) region of MUC1, which was prepared bearing multiple copies of the cancer-associated TN antigen. The glycopeptide thioester was prepared on the solid-phase using two different methods on 2-chlorotrityl chloride and sulfamylbutyryl resins. The solid-phase assembly on 2-chlorotrityl chloride resin, followed by thioesterification in solution, afforded the desired thioester in 4% yield over 41 linear steps. Likewise, the glycopeptide thioester was successfully prepared on sulfamylbutyryl resin using an activation and thiol-release strategy in a 9% isolated yield. The resulting peptide thioester was successfully ligated to a deprotected MUC1 glycopeptide using the direct aminolysis ligation to afford a 5.8 kDa, 40 amino acid MUC1 glycopeptide bearing 10 copies of the TN antigen. This work represents an important step toward the immunological evaluation of multivalent MUC1 constructs. | en |
dc.language | en | en |
dc.publisher | John Wiley & Sons, Inc | en |
dc.relation.ispartof | Biopolymers | en |
dc.title | Synthesis of MUC1 glycopeptide thioesters and ligation via direct aminolysis | en |
dc.type | Journal Article | en |
dc.identifier.doi | 10.1002/bip.21471 | en |
dc.subject.keywords | Proteins and Peptides | en |
dc.subject.keywords | Organic Chemical Synthesis | en |
local.contributor.firstname | Brendan | en |
local.contributor.firstname | Candy K Y | en |
local.contributor.firstname | Richard J | en |
local.subject.for2008 | 030503 Organic Chemical Synthesis | en |
local.subject.for2008 | 030406 Proteins and Peptides | en |
local.subject.seo2008 | 970103 Expanding Knowledge in the Chemical Sciences | en |
local.subject.seo2008 | 929999 Health not elsewhere classified | en |
local.profile.school | School of Science and Technology | en |
local.profile.email | bwilkin7@une.edu.au | en |
local.output.category | C1 | en |
local.record.place | au | en |
local.record.institution | University of New England | en |
local.identifier.epublicationsrecord | une-20170323-121928 | en |
local.publisher.place | United States of America | en |
local.format.startpage | 137 | en |
local.format.endpage | 146 | en |
local.identifier.scopusid | 79960687466 | en |
local.peerreviewed | Yes | en |
local.identifier.volume | 96 | en |
local.identifier.issue | 2 | en |
local.contributor.lastname | Wilkinson | en |
local.contributor.lastname | Chun | en |
local.contributor.lastname | Payne | en |
dc.identifier.staff | une-id:bwilkin7 | en |
local.profile.orcid | 0000-0003-1866-6540 | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.profile.role | author | en |
local.identifier.unepublicationid | une:20505 | en |
dc.identifier.academiclevel | Academic | en |
local.title.maintitle | Synthesis of MUC1 glycopeptide thioesters and ligation via direct aminolysis | en |
local.output.categorydescription | C1 Refereed Article in a Scholarly Journal | en |
local.search.author | Wilkinson, Brendan | en |
local.search.author | Chun, Candy K Y | en |
local.search.author | Payne, Richard J | en |
local.uneassociation | Unknown | en |
local.year.published | 2011 | en |
local.subject.for2020 | 340407 Proteins and peptides | en |
local.subject.for2020 | 340503 Organic chemical synthesis | en |
local.codeupdate.date | 2022-02-13T16:49:41.429 | en |
local.codeupdate.eperson | bwilkin7@une.edu.au | en |
local.codeupdate.finalised | true | en |
Appears in Collections: | Journal Article |
Files in This Item:
File | Description | Size | Format |
---|
Items in Research UNE are protected by copyright, with all rights reserved, unless otherwise indicated.