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...
Autores principales: | , , , , , , |
---|---|
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 |