Cargando…

Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry

Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The...

Descripción completa

Detalles Bibliográficos
Autores principales: Fürniss, Daniel, Mack, Timo, Hahn, Frank, Vollrath, Sidonie B L, Koroniak, Katarzyna, Schepers, Ute, Bräse, Stefan
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566861/
https://www.ncbi.nlm.nih.gov/pubmed/23399592
http://dx.doi.org/10.3762/bjoc.9.7
_version_ 1782258614565601280
author Fürniss, Daniel
Mack, Timo
Hahn, Frank
Vollrath, Sidonie B L
Koroniak, Katarzyna
Schepers, Ute
Bräse, Stefan
author_facet Fürniss, Daniel
Mack, Timo
Hahn, Frank
Vollrath, Sidonie B L
Koroniak, Katarzyna
Schepers, Ute
Bräse, Stefan
author_sort Fürniss, Daniel
collection PubMed
description Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described.
format Online
Article
Text
id pubmed-3566861
institution National Center for Biotechnology Information
language English
publishDate 2013
publisher Beilstein-Institut
record_format MEDLINE/PubMed
spelling pubmed-35668612013-02-11 Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry Fürniss, Daniel Mack, Timo Hahn, Frank Vollrath, Sidonie B L Koroniak, Katarzyna Schepers, Ute Bräse, Stefan Beilstein J Org Chem Full Research Paper Sugar moieties are present in a wide range of bioactive molecules. Thus, having versatile and fast methods for the decoration of biomimetic molecules with sugars is of fundamental importance. The glycosylation of peptoids and polyamines as examples of such biomimetic molecules is reported here. The method uses Cu-catalyzed azide alkyne cycloaddition to promote the reaction of azidosugars with either polyamines or peptoids. In addition, functionalized nucleic acids were attached to polyamines via the same route. Based on a modular solid-phase synthesis of peralkynylated peptoids with up to six alkyne groups, the latter were modified with azidosugar building blocks by using copper-catalyzed azide alkyne cycloadditions. In addition, the up-scaling of some particular azide-modified sugars is described. Beilstein-Institut 2013-01-10 /pmc/articles/PMC3566861/ /pubmed/23399592 http://dx.doi.org/10.3762/bjoc.9.7 Text en Copyright © 2013, Fürniss 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
Fürniss, Daniel
Mack, Timo
Hahn, Frank
Vollrath, Sidonie B L
Koroniak, Katarzyna
Schepers, Ute
Bräse, Stefan
Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
title Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
title_full Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
title_fullStr Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
title_full_unstemmed Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
title_short Peptoids and polyamines going sweet: Modular synthesis of glycosylated peptoids and polyamines using click chemistry
title_sort peptoids and polyamines going sweet: modular synthesis of glycosylated peptoids and polyamines using click chemistry
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3566861/
https://www.ncbi.nlm.nih.gov/pubmed/23399592
http://dx.doi.org/10.3762/bjoc.9.7
work_keys_str_mv AT furnissdaniel peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry
AT macktimo peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry
AT hahnfrank peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry
AT vollrathsidoniebl peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry
AT koroniakkatarzyna peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry
AT schepersute peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry
AT brasestefan peptoidsandpolyaminesgoingsweetmodularsynthesisofglycosylatedpeptoidsandpolyaminesusingclickchemistry