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Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling

C(sp(3))–H and C(sp(2))–H glycosylations of structurally complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed peptide–saccharide conjugation provided modular access to structurally complex C-alkyl glycoamino acids, glycopept...

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Autores principales: Wu, Jun, Kaplaneris, Nikolaos, Ni, Shaofei, Kaltenhäuser, Felix, Ackermann, Lutz
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152807/
https://www.ncbi.nlm.nih.gov/pubmed/34094117
http://dx.doi.org/10.1039/d0sc01260b
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author Wu, Jun
Kaplaneris, Nikolaos
Ni, Shaofei
Kaltenhäuser, Felix
Ackermann, Lutz
author_facet Wu, Jun
Kaplaneris, Nikolaos
Ni, Shaofei
Kaltenhäuser, Felix
Ackermann, Lutz
author_sort Wu, Jun
collection PubMed
description C(sp(3))–H and C(sp(2))–H glycosylations of structurally complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed peptide–saccharide conjugation provided modular access to structurally complex C-alkyl glycoamino acids, glycopeptides and C-aryl glycosides, while enabling the assembly of fluorescent-labeled glycoamino acids. The C–H activation approach represents an expedient and efficient strategy for peptide late-stage diversification in a programmable as well as chemo-, regio-, and diastereo-selective fashion.
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spelling pubmed-81528072021-06-04 Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling Wu, Jun Kaplaneris, Nikolaos Ni, Shaofei Kaltenhäuser, Felix Ackermann, Lutz Chem Sci Chemistry C(sp(3))–H and C(sp(2))–H glycosylations of structurally complex amino acids and peptides were accomplished through the assistance of triazole peptide-isosteres. The palladium-catalyzed peptide–saccharide conjugation provided modular access to structurally complex C-alkyl glycoamino acids, glycopeptides and C-aryl glycosides, while enabling the assembly of fluorescent-labeled glycoamino acids. The C–H activation approach represents an expedient and efficient strategy for peptide late-stage diversification in a programmable as well as chemo-, regio-, and diastereo-selective fashion. The Royal Society of Chemistry 2020-03-24 /pmc/articles/PMC8152807/ /pubmed/34094117 http://dx.doi.org/10.1039/d0sc01260b Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Wu, Jun
Kaplaneris, Nikolaos
Ni, Shaofei
Kaltenhäuser, Felix
Ackermann, Lutz
Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
title Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
title_full Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
title_fullStr Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
title_full_unstemmed Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
title_short Late-stage C(sp(2))–H and C(sp(3))–H glycosylation of C-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
title_sort late-stage c(sp(2))–h and c(sp(3))–h glycosylation of c-aryl/alkyl glycopeptides: mechanistic insights and fluorescence labeling
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8152807/
https://www.ncbi.nlm.nih.gov/pubmed/34094117
http://dx.doi.org/10.1039/d0sc01260b
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