The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates

The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani–Fischer C-elongation reaction of the corresponding aldohexoses, glycoco...

Descripción completa

Detalles Bibliográficos
Autores principales: Gallas, Katharina, Pototschnig, Gerit, Adanitsch, Florian, Stütz, Arnold E, Wrodnigg, Tanja M
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2012
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3510994/
https://www.ncbi.nlm.nih.gov/pubmed/23209494
http://dx.doi.org/10.3762/bjoc.8.185
_version_ 1782251530047455232
author Gallas, Katharina
Pototschnig, Gerit
Adanitsch, Florian
Stütz, Arnold E
Wrodnigg, Tanja M
author_facet Gallas, Katharina
Pototschnig, Gerit
Adanitsch, Florian
Stütz, Arnold E
Wrodnigg, Tanja M
author_sort Gallas, Katharina
collection PubMed
description The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani–Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following this strategy, non-natural C-glycosyl type glycoconjugates, which can be utilised as building blocks for the composition of larger molecular constructions, are available by a very short synthetic approach.
format Online
Article
Text
id pubmed-3510994
institution National Center for Biotechnology Information
language English
publishDate 2012
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-35109942012-12-03 The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates Gallas, Katharina Pototschnig, Gerit Adanitsch, Florian Stütz, Arnold E Wrodnigg, Tanja M Beilstein J Org Chem Full Research Paper The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani–Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following this strategy, non-natural C-glycosyl type glycoconjugates, which can be utilised as building blocks for the composition of larger molecular constructions, are available by a very short synthetic approach. Beilstein-Institut 2012-09-25 /pmc/articles/PMC3510994/ /pubmed/23209494 http://dx.doi.org/10.3762/bjoc.8.185 Text en Copyright © 2012, Gallas et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Gallas, Katharina
Pototschnig, Gerit
Adanitsch, Florian
Stütz, Arnold E
Wrodnigg, Tanja M
The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
title The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
title_full The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
title_fullStr The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
title_full_unstemmed The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
title_short The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural C-glycosyl type glycoconjugates
title_sort amadori rearrangement as glycoconjugation method: synthesis of non-natural c-glycosyl type glycoconjugates
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3510994/
https://www.ncbi.nlm.nih.gov/pubmed/23209494
http://dx.doi.org/10.3762/bjoc.8.185
work_keys_str_mv AT gallaskatharina theamadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT pototschniggerit theamadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT adanitschflorian theamadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT stutzarnolde theamadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT wrodniggtanjam theamadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT gallaskatharina amadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT pototschniggerit amadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT adanitschflorian amadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT stutzarnolde amadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates
AT wrodniggtanjam amadorirearrangementasglycoconjugationmethodsynthesisofnonnaturalcglycosyltypeglycoconjugates

Ejemplares similares