Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation
Carbohydrate recognition is essential in cellular interactions and biological processes. It is characterized by structural diversity, multivalency and cooperative effects. To evaluate carbohydrate interaction and recognition, the structurally defined attachment of sugar units to a rigid template is...
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doaj-067c5af894b44193b9c5406c024516072021-02-02T07:50:15ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-04-0110194895510.3762/bjoc.10.931860-5397-10-93Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformationNitin J. Pawar0Navdeep S. Sidhu1George M. Sheldrick2Dilip D. Dhavale3Ulf Diederichsen4Institute for Organic and Biomolecular Chemistry, Georg-August University Göttingen, Tammannstrasse 2, D-37077 Göttingen, GermanyInstitute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstraße 4, D-37077 Göttingen, GermanyInstitute for Inorganic Chemistry, Georg-August University Göttingen, Tammannstraße 4, D-37077 Göttingen, GermanyDepartment of Chemistry, Garware Research Centre, University of Pune, Pune 411 007, IndiaInstitute for Organic and Biomolecular Chemistry, Georg-August University Göttingen, Tammannstrasse 2, D-37077 Göttingen, GermanyCarbohydrate recognition is essential in cellular interactions and biological processes. It is characterized by structural diversity, multivalency and cooperative effects. To evaluate carbohydrate interaction and recognition, the structurally defined attachment of sugar units to a rigid template is highly desired. β-Peptide helices offer conformationally stable templates for the linear presentation of sugar units in defined distances. The synthesis and β-peptide incorporation of sugar-β-amino acids are described providing the saccharide units as amino acid side chain. The respective sugar-β-amino acids are accessible by Michael addition of ammonia to sugar units derivatized as α,β-unsaturated esters. Three sugar units were incorporated in β-peptide oligomers varying the sugar (glucose, galactose, xylose) and sugar protecting groups. The influence of sugar units and the configuration of sugar-β-amino acids on β-peptide secondary structure were investigated by CD spectroscopy.https://doi.org/10.3762/bjoc.10.93carbohydrate recognitionconformationglycopeptideβ-peptidesugar amino acid |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Nitin J. Pawar Navdeep S. Sidhu George M. Sheldrick Dilip D. Dhavale Ulf Diederichsen |
spellingShingle |
Nitin J. Pawar Navdeep S. Sidhu George M. Sheldrick Dilip D. Dhavale Ulf Diederichsen Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation Beilstein Journal of Organic Chemistry carbohydrate recognition conformation glycopeptide β-peptide sugar amino acid |
author_facet |
Nitin J. Pawar Navdeep S. Sidhu George M. Sheldrick Dilip D. Dhavale Ulf Diederichsen |
author_sort |
Nitin J. Pawar |
title |
Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation |
title_short |
Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation |
title_full |
Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation |
title_fullStr |
Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation |
title_full_unstemmed |
Molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation |
title_sort |
molecular architecture with carbohydrate functionalized β-peptides adopting 314-helical conformation |
publisher |
Beilstein-Institut |
series |
Beilstein Journal of Organic Chemistry |
issn |
1860-5397 |
publishDate |
2014-04-01 |
description |
Carbohydrate recognition is essential in cellular interactions and biological processes. It is characterized by structural diversity, multivalency and cooperative effects. To evaluate carbohydrate interaction and recognition, the structurally defined attachment of sugar units to a rigid template is highly desired. β-Peptide helices offer conformationally stable templates for the linear presentation of sugar units in defined distances. The synthesis and β-peptide incorporation of sugar-β-amino acids are described providing the saccharide units as amino acid side chain. The respective sugar-β-amino acids are accessible by Michael addition of ammonia to sugar units derivatized as α,β-unsaturated esters. Three sugar units were incorporated in β-peptide oligomers varying the sugar (glucose, galactose, xylose) and sugar protecting groups. The influence of sugar units and the configuration of sugar-β-amino acids on β-peptide secondary structure were investigated by CD spectroscopy. |
topic |
carbohydrate recognition conformation glycopeptide β-peptide sugar amino acid |
url |
https://doi.org/10.3762/bjoc.10.93 |
work_keys_str_mv |
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