A Malonyl-Based Scaffold for Conjugatable Multivalent Carbohydrate-BODIPY Presentations.
BODIPY
conjugation
glycosylation
monosaccharide
multivalent presentation
tetravalent scaffold
Journal
Molecules (Basel, Switzerland)
ISSN: 1420-3049
Titre abrégé: Molecules
Pays: Switzerland
ID NLM: 100964009
Informations de publication
Date de publication:
29 May 2019
29 May 2019
Historique:
received:
11
04
2019
revised:
23
05
2019
accepted:
27
05
2019
entrez:
1
6
2019
pubmed:
31
5
2019
medline:
26
11
2019
Statut:
epublish
Résumé
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.
Identifiants
pubmed: 31146429
pii: molecules24112050
doi: 10.3390/molecules24112050
pmc: PMC6600552
pii:
doi:
Substances chimiques
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
0
Boron Compounds
0
Carbohydrates
0
Malonates
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Subventions
Organisme : Ministerio de Economia y Competitividad (MINECO) Spain
ID : CTQ2015-66702-R
Organisme : Ministerio de Economia y Competitividad (MINECO) Spain
ID : MAT2017-83856-C3-3-P
Organisme : Govierno Vasco, Spain
ID : IT912-16
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