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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
The Royal Society of Chemistry
2020
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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. |
format | Online Article Text |
id | pubmed-8152807 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | The Royal Society of Chemistry |
record_format | MEDLINE/PubMed |
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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