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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

  • Czech description

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