Cargando…
A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux
Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongoing research aimed at the synthesis of sulfonic acid-containi...
Autores principales: | , , , , |
---|---|
Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2016
|
Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274384/ https://www.ncbi.nlm.nih.gov/pubmed/27845725 http://dx.doi.org/10.3390/molecules21111497 |
_version_ | 1783377605598117888 |
---|---|
author | Mező, Erika Eszenyi, Dániel Varga, Eszter Herczeg, Mihály Borbás, Anikó |
author_facet | Mező, Erika Eszenyi, Dániel Varga, Eszter Herczeg, Mihály Borbás, Anikó |
author_sort | Mező, Erika |
collection | PubMed |
description | Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongoing research aimed at the synthesis of sulfonic acid-containing heparinoid anticoagulants, we elaborated a modular pathway to obtain a series of idraparinux-analogue pentasaccharides bearing one or two primary sulfonic acid moieties. Five protected pentasaccharides with different C-sulfonation patterns were prepared by two subsequent glycosylation reactions, respectively, using two monosaccharide and four disaccharide building blocks. Transformation of the protected derivatives into the fully O-sulfated, O-methylated sulfonic acid end-products was also studied. |
format | Online Article Text |
id | pubmed-6274384 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-62743842018-12-28 A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux Mező, Erika Eszenyi, Dániel Varga, Eszter Herczeg, Mihály Borbás, Anikó Molecules Article Heparin-based anticoagulants are drugs of choice in the therapy and prophylaxis of thromboembolic diseases. Idraparinux is a synthetic anticoagulant pentasaccharide based on the heparin antithrombin-binding domain. In the frame of our ongoing research aimed at the synthesis of sulfonic acid-containing heparinoid anticoagulants, we elaborated a modular pathway to obtain a series of idraparinux-analogue pentasaccharides bearing one or two primary sulfonic acid moieties. Five protected pentasaccharides with different C-sulfonation patterns were prepared by two subsequent glycosylation reactions, respectively, using two monosaccharide and four disaccharide building blocks. Transformation of the protected derivatives into the fully O-sulfated, O-methylated sulfonic acid end-products was also studied. MDPI 2016-11-11 /pmc/articles/PMC6274384/ /pubmed/27845725 http://dx.doi.org/10.3390/molecules21111497 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Mező, Erika Eszenyi, Dániel Varga, Eszter Herczeg, Mihály Borbás, Anikó A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux |
title | A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux |
title_full | A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux |
title_fullStr | A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux |
title_full_unstemmed | A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux |
title_short | A Modular Synthetic Approach to Isosteric Sulfonic Acid Analogues of the Anticoagulant Pentasaccharide Idraparinux |
title_sort | modular synthetic approach to isosteric sulfonic acid analogues of the anticoagulant pentasaccharide idraparinux |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6274384/ https://www.ncbi.nlm.nih.gov/pubmed/27845725 http://dx.doi.org/10.3390/molecules21111497 |
work_keys_str_mv | AT mezoerika amodularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT eszenyidaniel amodularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT vargaeszter amodularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT herczegmihaly amodularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT borbasaniko amodularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT mezoerika modularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT eszenyidaniel modularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT vargaeszter modularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT herczegmihaly modularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux AT borbasaniko modularsyntheticapproachtoisostericsulfonicacidanaloguesoftheanticoagulantpentasaccharideidraparinux |