One-step preparation of 6-perfluoroalkylalkanoates of trehalose and sucrose for biomedical uses.
The Mitsunobu reaction has been used to obtain 6-polyfluoroalkanoates of alpha,alpha-trehalose and sucrose in yields of approximately 40% and approximately 25%, respectively. 6,6'-Diesters (3-6%) were formed in some reactions and a 6-ester (1.3%) of alpha-D-glucopyranosyl 3,4-anhydro-beta-D-tagatofuranoside in one reaction. The monoesters displayed strong surfactant properties, and reduced considerably the water surface and fluorocarbon/water interfacial tensions. Preliminary results on biocompatibility were encouraging, especially for the 6-esters of alpha,alpha-trehalose.
Abouhilale
S
S
Laboratoire de Chimie Moléculaire, C.N.R.S., Université de Nice-Sophia, Nice, France.
Greiner
J
J
Riess
J G
JG
D000818:Animals; D001672:Biocompatible Materials; D001802:Blood Substitutes; D002240:Carbohydrate Sequence; D004912:Erythrocytes / Q000187:drug effects; D006461:Hemolysis; D006801:Humans; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000494:pharmacology; D051379:Mice; D008969:Molecular Sequence Data; D013395:Sucrose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D014199:Trehalose / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry*
D001672:Biocompatible Materials; D001802:Blood Substitutes; D006845:Hydrocarbons, Fluorinated; D013395:Sucrose; D014199:Trehalose