In this work, we report the synthesis of a new series of glucocationic surfactants, a class of surfactants we introduced very recently. The preparation of the surfactants is based on the synthesis of the 2-bromoethyl-2,3,4,6-tetra-O-acetyl--D-glucopyranoside, whose preparation was studied in order to improve yields and stereoselectivity of this key intermediate. These glucocationic amphiphiles were prepared and studied as a model of cationic surfactants marked with a carbohydrate moiety. The use of carbohydrates as markers on cationic lipids was recently introduced to induce recognition by specific receptors, present on the surface of cell membranes. The chemicophysical characterization of these model structures can give more insight on the aggregation behavior. Conductivity and surface tension measurements were performed in order to characterize the compounds from the amphiphilic point of view. The results showed a different effect of the glucosidic moiety on the cmc value with respect to the glucopyridinium cationic surfactants. The surfactants also showed the tendency to form premicellar aggregates in solution when the hydrophobicity is raised

Synthesis and Properties of New Glucocationic Surfactants: Model Structures for Marking Cationic Surfactants with Carbohydrates / P., Quagliotto; G., Viscardi; C., Barolo; D., Dangelo; E., Barni; Compari, Carlotta; Duce, Elenia; Fisicaro, Emilia. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 70:(2005), pp. 9857-9866. [10.1021/jo051579s]

Synthesis and Properties of New Glucocationic Surfactants: Model Structures for Marking Cationic Surfactants with Carbohydrates

COMPARI, Carlotta;DUCE, Elenia;FISICARO, Emilia
2005-01-01

Abstract

In this work, we report the synthesis of a new series of glucocationic surfactants, a class of surfactants we introduced very recently. The preparation of the surfactants is based on the synthesis of the 2-bromoethyl-2,3,4,6-tetra-O-acetyl--D-glucopyranoside, whose preparation was studied in order to improve yields and stereoselectivity of this key intermediate. These glucocationic amphiphiles were prepared and studied as a model of cationic surfactants marked with a carbohydrate moiety. The use of carbohydrates as markers on cationic lipids was recently introduced to induce recognition by specific receptors, present on the surface of cell membranes. The chemicophysical characterization of these model structures can give more insight on the aggregation behavior. Conductivity and surface tension measurements were performed in order to characterize the compounds from the amphiphilic point of view. The results showed a different effect of the glucosidic moiety on the cmc value with respect to the glucopyridinium cationic surfactants. The surfactants also showed the tendency to form premicellar aggregates in solution when the hydrophobicity is raised
2005
Synthesis and Properties of New Glucocationic Surfactants: Model Structures for Marking Cationic Surfactants with Carbohydrates / P., Quagliotto; G., Viscardi; C., Barolo; D., Dangelo; E., Barni; Compari, Carlotta; Duce, Elenia; Fisicaro, Emilia. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 70:(2005), pp. 9857-9866. [10.1021/jo051579s]
File in questo prodotto:
File Dimensione Formato  
JOC05.pdf

non disponibili

Tipologia: Documento in Post-print
Licenza: Creative commons
Dimensione 206.52 kB
Formato Adobe PDF
206.52 kB Adobe PDF   Visualizza/Apri   Richiedi una copia
JOCgluco2005.pdf

non disponibili

Tipologia: Abstract
Licenza: Creative commons
Dimensione 67.85 kB
Formato Adobe PDF
67.85 kB Adobe PDF   Visualizza/Apri   Richiedi una copia

I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.

Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11381/1444384
Citazioni
  • ???jsp.display-item.citation.pmc??? ND
  • Scopus 55
  • ???jsp.display-item.citation.isi??? 56
social impact