The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations

The Amadori rearrangement was investigated for the synthesis of C‐glycosyl‐type neoglycoconjugates. Various amines including diamines, amino‐functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non‐natural C‐glycosyl‐type glycoconjugates...

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Detalles Bibliográficos
Autores principales: Hojnik, Cornelia, Müller, Anne, Gloe, Tobias‐Elias, Lindhorst, Thisbe K., Wrodnigg, Tanja M.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2016
Materias:
Full Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5094532/
https://www.ncbi.nlm.nih.gov/pubmed/27840588
http://dx.doi.org/10.1002/ejoc.201600458
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author Hojnik, Cornelia
Müller, Anne
Gloe, Tobias‐Elias
Lindhorst, Thisbe K.
Wrodnigg, Tanja M.
author_facet Hojnik, Cornelia
Müller, Anne
Gloe, Tobias‐Elias
Lindhorst, Thisbe K.
Wrodnigg, Tanja M.
author_sort Hojnik, Cornelia
collection PubMed
description The Amadori rearrangement was investigated for the synthesis of C‐glycosyl‐type neoglycoconjugates. Various amines including diamines, amino‐functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non‐natural C‐glycosyl‐type glycoconjugates of the d‐gluco and d‐manno series. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.
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spelling pubmed-50945322016-11-09 The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations Hojnik, Cornelia Müller, Anne Gloe, Tobias‐Elias Lindhorst, Thisbe K. Wrodnigg, Tanja M. European J Org Chem Full Papers The Amadori rearrangement was investigated for the synthesis of C‐glycosyl‐type neoglycoconjugates. Various amines including diamines, amino‐functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non‐natural C‐glycosyl‐type glycoconjugates of the d‐gluco and d‐manno series. With these studies, the scope and limitations of the Amadori rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components. John Wiley and Sons Inc. 2016-06-27 2016-09 /pmc/articles/PMC5094532/ /pubmed/27840588 http://dx.doi.org/10.1002/ejoc.201600458 Text en © 2016 The Authors. Published by Wiley‐VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution (http://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Full Papers
Hojnik, Cornelia
Müller, Anne
Gloe, Tobias‐Elias
Lindhorst, Thisbe K.
Wrodnigg, Tanja M.
The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
title The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
title_full The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
title_fullStr The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
title_full_unstemmed The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
title_short The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
title_sort amadori rearrangement for carbohydrate conjugation: scope and limitations
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5094532/
https://www.ncbi.nlm.nih.gov/pubmed/27840588
http://dx.doi.org/10.1002/ejoc.201600458
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