2024-03-29T11:27:01Zhttp://digital.csic.es/dspace-oai/requestoai:digital.csic.es:10261/782952022-01-26T08:33:37Zcom_10261_81com_10261_5com_10261_86com_10261_1com_10261_34col_10261_334col_10261_339col_10261_287
00925njm 22002777a 4500
dc
Carrero, Paula
author
Ardá, Ana
author
Alvarez, Mónica
author
García-Doyagüez, Elisa
author
Rivero-Buceta, Eva
author
Quesada, Ernesto
author
Prieto, Alicia
author
Solís, Dolores
author
Camarasa Rius, María José
author
Peréz-Pérez, María-Jesús
author
Jiménez-Barbero, Jesús
author
San-Félix, Ana
author
2013
The tripodal receptors 1 and 2 based on a triethylbenzene
scaffold substituted with trihydroxybenzoyl groups have
been synthesised. The conformational preferences and
carbohydrate-binding ability of 1 and 2 have been examined
by NMR spectroscopy and modelling procedures. The results
reveal that the particular structural pre-organisation of 2 facilitates
the recognition, in a highly competitive medium
(DMSO), of a mannose-based polysaccharide consisting of a
linear saccharide chain continuously decorated by α(1 2)-linked branching mannose moieties. By contrast, other
α(1 2)-substituted polysaccharides or different monosaccharides
are not bound, revealing the selectivity of the interaction.
Due to the importance of α(1 2) mannosides, which
are abundantly present on the glycan shield of several pathogens,
the results reported here open attractive prospects for
the potential application of 2 or its derivatives in future antiinfective
strategies.
European Journal of Organic Chemistry (1) : 65-76 (2013)
1434-193X
http://hdl.handle.net/10261/78295
10.1002/ejoc.201201239
1099-0690
http://dx.doi.org/10.13039/501100003339
http://dx.doi.org/10.13039/501100004587
http://dx.doi.org/10.13039/100012818
Carbohydrates
Conformational analysis
Molecular recognition
Receptors
Differential Recognition of Mannose-Based Polysaccharides by Tripodal Receptors Based on a Triethylbenzene Scaffold Substituted with Trihydroxybenzoyl Moieties