Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase

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Standard

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

Harvard

Fischer, NH, Vævest, BN, Dam, AK, Diness, F & Pedersen, CM 2024, 'Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase', ChemPlusChem. https://doi.org/10.1002/cplu.202400066

APA

Fischer, N. H., Vævest, B. N., Dam, A. K., Diness, F., & Pedersen, C. M. (Accepteret/In press). Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase. ChemPlusChem, [e202400066]. https://doi.org/10.1002/cplu.202400066

Vancouver

Fischer NH, Vævest BN, Dam AK, Diness F, Pedersen CM. Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase. ChemPlusChem. 2024. e202400066. https://doi.org/10.1002/cplu.202400066

Author

Fischer, Niklas H. ; Vævest, Benedicte N. ; Dam, Andreas K. ; Diness, Frederik ; Pedersen, Christian M. / Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase. I: ChemPlusChem. 2024.

Bibtex

@article{a5c9d6ea4a0d4bf4a5cf9e4e1d12f7d2,

title = "Self-Promoted Glycosylation of Carbamoylated Peptides on Solid Phase",

abstract = "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.",

keywords = "glycosylation, N-glycosides, neoglycopeptides, self-promotion, solid-phase synthesis",

author = "Fischer, {Niklas H.} and V{\ae}vest, {Benedicte N.} and Dam, {Andreas K.} and Frederik Diness and Pedersen, {Christian M.}",

note = "Publisher Copyright: {\textcopyright} 2024 The Authors. ChemPlusChem published by Wiley-VCH GmbH.",

year = "2024",

doi = "10.1002/cplu.202400066",

language = "English",

journal = "ChemPlusChem",

issn = "2192-6506",

publisher = "Wiley - V C H Verlag GmbH & Co. KGaA",

}

RIS

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.

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

Kemisk Institut