Cargando…

A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations

A concise synthetic route from methylmalonate to a tetravalent aliphatic scaffold has been developed. The ensuing tetra-tethered derivative is equipped with two hydroxyl groups, as well as orthogonal alkene and alkyne functionalities. The usefulness of the scaffold has been demonstrated with the pre...

Descripción completa

Detalles Bibliográficos
Autores principales: Uriel, Clara, Sola-Llano, Rebeca, Bañuelos, Jorge, Gomez, Ana M., Lopez, J. Cristobal
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600552/
https://www.ncbi.nlm.nih.gov/pubmed/31146429
http://dx.doi.org/10.3390/molecules24112050
_version_ 1783431142842564608
author Uriel, Clara
Sola-Llano, Rebeca
Bañuelos, Jorge
Gomez, Ana M.
Lopez, J. Cristobal
author_facet Uriel, Clara
Sola-Llano, Rebeca
Bañuelos, Jorge
Gomez, Ana M.
Lopez, J. Cristobal
author_sort Uriel, Clara
collection PubMed
description A concise synthetic route from methylmalonate to a tetravalent aliphatic scaffold has been developed. The ensuing tetra-tethered derivative is equipped with two hydroxyl groups, as well as orthogonal alkene and alkyne functionalities. The usefulness of the scaffold has been demonstrated with the preparation of two representative multivalent derivatives: (i) a tetravalent compound containing two D-mannose units, one fluorescent boron-dipyrromethene (BODIPY) dye and a suitably functionalized amino acid and (ii) by way of dimerization and saponification, a water-soluble tetramannan derivative containing two fluorescent BODIPY units. Additionally, photophysical measurements conducted on these derivatives support the viability of the herein designed single and double BODIPY-labeled carbohydrate-based clusters as fluorescent markers.
format Online
Article
Text
id pubmed-6600552
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-66005522019-07-16 A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations Uriel, Clara Sola-Llano, Rebeca Bañuelos, Jorge Gomez, Ana M. Lopez, J. Cristobal Molecules Communication A concise synthetic route from methylmalonate to a tetravalent aliphatic scaffold has been developed. The ensuing tetra-tethered derivative is equipped with two hydroxyl groups, as well as orthogonal alkene and alkyne functionalities. The usefulness of the scaffold has been demonstrated with the preparation of two representative multivalent derivatives: (i) a tetravalent compound containing two D-mannose units, one fluorescent boron-dipyrromethene (BODIPY) dye and a suitably functionalized amino acid and (ii) by way of dimerization and saponification, a water-soluble tetramannan derivative containing two fluorescent BODIPY units. Additionally, photophysical measurements conducted on these derivatives support the viability of the herein designed single and double BODIPY-labeled carbohydrate-based clusters as fluorescent markers. MDPI 2019-05-29 /pmc/articles/PMC6600552/ /pubmed/31146429 http://dx.doi.org/10.3390/molecules24112050 Text en © 2019 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 Communication
Uriel, Clara
Sola-Llano, Rebeca
Bañuelos, Jorge
Gomez, Ana M.
Lopez, J. Cristobal
A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations
title A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations
title_full A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations
title_fullStr A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations
title_full_unstemmed A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations
title_short A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations
title_sort malonyl-based scaffold for conjugatable multivalent carbohydrate-bodipy presentations
topic Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600552/
https://www.ncbi.nlm.nih.gov/pubmed/31146429
http://dx.doi.org/10.3390/molecules24112050
work_keys_str_mv AT urielclara amalonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT solallanorebeca amalonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT banuelosjorge amalonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT gomezanam amalonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT lopezjcristobal amalonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT urielclara malonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT solallanorebeca malonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT banuelosjorge malonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT gomezanam malonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations
AT lopezjcristobal malonylbasedscaffoldforconjugatablemultivalentcarbohydratebodipypresentations