Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase
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Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase. / Fischer, Niklas H.; Vævest, Benedicte N.; Dam, Andreas K.; Diness, Frederik; Pedersen, Christian M.
I: ChemPlusChem, 2024.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › Forskning › fagfællebedømt
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TY - JOUR
T1 - Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase
AU - Fischer, Niklas H.
AU - Vævest, Benedicte N.
AU - Dam, Andreas K.
AU - Diness, Frederik
AU - Pedersen, Christian M.
N1 - Publisher Copyright: © 2024 The Authors. ChemPlusChem published by Wiley-VCH GmbH.
PY - 2024
Y1 - 2024
N2 - Self-promoted glycosylations with trichloroacetimidate glycosyl donors are demonstrated on solid-phase-anchored peptides orthogonally deprotected and tosylcarbamoylated on the side-chains of cysteine and serine, respectively. The donor scope included glucosyl as well as mannosyl trichloroacetimidates, carrying benzyl, acetyl, or isopropylidene protecting groups. Isopropylidene groups were found to be removed under the acidic conditions used for release of the neoglycopeptides from the solid support, yielding neoglycopeptides with unprotected hydroxyl groups. Glycosylation of a peptide containing a carbamoylated tyrosine was attempted as well, but the desired neoglycopeptide could not be synthesized due to thermal instability of the carbamate.
AB - Self-promoted glycosylations with trichloroacetimidate glycosyl donors are demonstrated on solid-phase-anchored peptides orthogonally deprotected and tosylcarbamoylated on the side-chains of cysteine and serine, respectively. The donor scope included glucosyl as well as mannosyl trichloroacetimidates, carrying benzyl, acetyl, or isopropylidene protecting groups. Isopropylidene groups were found to be removed under the acidic conditions used for release of the neoglycopeptides from the solid support, yielding neoglycopeptides with unprotected hydroxyl groups. Glycosylation of a peptide containing a carbamoylated tyrosine was attempted as well, but the desired neoglycopeptide could not be synthesized due to thermal instability of the carbamate.
KW - glycosylation
KW - N-glycosides
KW - neoglycopeptides
KW - self-promotion
KW - solid-phase synthesis
U2 - 10.1002/cplu.202400066
DO - 10.1002/cplu.202400066
M3 - Journal article
C2 - 38523065
AN - SCOPUS:85190138274
JO - ChemPlusChem
JF - ChemPlusChem
SN - 2192-6506
M1 - e202400066
ER -
ID: 389416935