Development of α-Selective Glycosylation for the Synthesis of Deoxyfluorinated TN Antigen Analogues.
The result's identifiers
Result code in IS VaVaI
<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F67985858%3A_____%2F21%3A00541038" target="_blank" >RIV/67985858:_____/21:00541038 - isvavai.cz</a>
Alternative codes found
RIV/60461373:22310/21:43923756
Result on the web
<a href="http://hdl.handle.net/11104/0318603" target="_blank" >http://hdl.handle.net/11104/0318603</a>
DOI - Digital Object Identifier
<a href="http://dx.doi.org/10.1021/acs.joc.0c03015" target="_blank" >10.1021/acs.joc.0c03015</a>
Alternative languages
Result language
angličtina
Original language name
Development of α-Selective Glycosylation for the Synthesis of Deoxyfluorinated TN Antigen Analogues.
Original language description
The Tn antigen (GalNAcα1-Thr/Ser) is abundantly expressed in many tumors but rarely found in healthy tissues, which makes it an attractive epitope for antitumor immunotherapy. The use of the Tn antigen in the development of therapeutic antitumor vaccines is hampered by its low immunogenicity, which may be enhanced by deoxyfluorination of the GalNAc moiety. Here, we report the synthesis of protected 3- and 4-fluoro analogues of the threonine-containing Tn antigen. As the stereoselective synthesis of α-linked fluorinated GalNAc is difficult, we prepared a panel of C3 and C4 deoxyfluorinated galactosazide thiodonors and evaluated their stereoselectivity in the glycosylation of carbohydrate acceptors and threonine derivatives. Glycosylation of threonine derivatives with O-benzylated C4 fluoro donors gave only modest but usable α-selectivity of α/β = 2.5–3/1. The use of acyl and silyl protection at the 3- and 6-positions of the C4 fluoro donors did not enhance the selectivity. Installing a 4,6-di-tert-butylsilylene-protecting group in C3 fluoro donors resulted in exclusive α-selectivity and reaffirmed the strong α-directing effect of this protective group in glycosylation with galacto-configured glycosyl donors.
Czech name
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Czech description
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Classification
Type
J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database
CEP classification
—
OECD FORD branch
10401 - Organic chemistry
Result continuities
Project
<a href="/en/project/GA17-18203S" target="_blank" >GA17-18203S: Stereodirecting effects of deoxofluorination at C-3 and C-4 of 2-azido-2-deoxy-hexopyranosyl donors</a><br>
Continuities
P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)
Others
Publication year
2021
Confidentiality
S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů
Data specific for result type
Name of the periodical
Journal of Organic Chemistry
ISSN
0022-3263
e-ISSN
1520-6904
Volume of the periodical
86
Issue of the periodical within the volume
7
Country of publishing house
US - UNITED STATES
Number of pages
18
Pages from-to
5073-5090
UT code for WoS article
000637001800016
EID of the result in the Scopus database
2-s2.0-85103462689