UMYMFOR 05516
UNIDAD DE MICROANALISIS Y METODOS FISICOS EN QUIMICA ORGANICA
Unidad Ejecutora - UE
artículos
Título:
Multivalent assembly of a pyrene functionalized thio-N-acetylglucosamine: Synthesis, spectroscopic and WGA binding studies
Autor/es:
DI CHENNA, PABLO H.; SPAGNUOLO, CARLA C.; MONTENEGRO, HUGO O.; UHRIG, MARÍA LAURA
Revista:
CARBOHYDRATE RESEARCH
Editorial:
ELSEVIER SCI LTD
Referencias:
Año: 2019 vol. 479 p. 6 - 12
ISSN:
0008-6215
Resumen:
We introduce here a new fluorescent derivative of 1-thio-β-N-acetylglucosamine linked to a pyrene systemthroughatriazolylpentylspacer,designedtoself-assembleintoamultivalentglycocluster.ThesynthesiswasachievedbyefficientCuAACclickreactionbetweenapyrenefunctionalizedwithanazidegroupandasuitablealkynylthiomonosaccharide.Spectroscopicstudiesbyfluorometryindicatedthattheself-assemblyinaqueousmediumismodulatedbyconcentrationandpHchanges,thelatterduetothepresenceoftheaminogroupclosetotheπsystem.Circulardichroismexperimentsrevealedamoderatepositivesignal,suggestingthatthepyrene-thioGlcNAcconjugatecanaggregateintoachiralsupramolecularassembly.Thesugarmoietyshowedtospe-cificallyandreversiblyinteractwiththewheatgermagglutinin,afactthatwasdemonstratedbyturbidityassay.SEMmicroscopyofalyophilizedsolutionatpH10revealedafibrillarmorphologycompatiblewiththepresenceoftubularmicelles,whereascrystallineandamorphoussolidsareformedatlowerpHs
