RESUMO
The mono-glucose-branched cyclodextrins having an appropriate spacer between the beta-cyclodextrin and a glucose moiety were synthesized from beta-cyclodextrin and arbutin. They had the significantly high association constants for doxorubicin, the anticancer agent, in the range of 10(5)-10(6)M(-1), and worked as highly reactive glycosyl acceptors for the transglycosylation reaction by endo-beta-N-acetylglucosaminidase of Mucor hiemalis to produce sialo-complex type oligosaccharide-branched cyclodextrins in the high yields of 65-67%.
Assuntos
Acetilglucosaminidase/metabolismo , Ciclodextrinas/síntese química , Doxorrubicina/química , Portadores de Fármacos/síntese química , Mucor/enzimologia , Antineoplásicos/administração & dosagem , Sítios de Ligação , Ciclodextrinas/química , Sistemas de Liberação de Medicamentos , Glucose/química , Glicosilação , Modelos Moleculares , Oligossacarídeos/químicaRESUMO
We investigated the transglycosylation reaction of the recombinant endo-beta-N-acetylglucosaminidase from Mucor hiemalis (Endo-M) expressed in Candida boidinii using such sugar derivatives as N-acylated d-glucosamines, C-glucosyl derivatives, and a 2-O-glycosylated disaccharide as acceptors. We found that a variety of sugar derivatives modified at C-1 or C-2 could be used as acceptors for transglycosylation by Endo-M to create novel oligosaccharides.
Assuntos
Manosil-Glicoproteína Endo-beta-N-Acetilglucosaminidase/química , Mucor/enzimologia , Oligossacarídeos/química , Acetilglucosamina/análogos & derivados , Acetilglucosamina/química , Dissacarídeos/química , Glicosilação , Estrutura MolecularRESUMO
We examined the transglycosylation reaction by the recombinant endo-beta-N-acetylglucosaminidase from Mucor hiemalis (Endo-M) expressed in Candida boidinii in media containing organic solvents. The recombinant Endo-M could transglycosylate a disialo biantennary complex-type oligosaccharide from hen egg yolk glycopeptide to p-nitrophenyl N-acetyl-beta-D-glucosaminide even in the presence of 30% acetone, dimethyl sulfoxide, or methanol. The yield of the transglycosylation product reached 21-34% of the total amount of acceptor, while the yield was only about 14% in aqueous solution.