Glycosidic Bond Expanded Cyclic Oligosaccharides:
Synthesis and Host–Guest Binding Property of a Cyclic Pentasaccharide
Gopal
Ch Samanta
Krishnagopal Maiti
Narayanaswamy Jayaraman
10.1021/acsomega.8b00580.s001
https://acs.figshare.com/articles/journal_contribution/Glycosidic_Bond_Expanded_Cyclic_Oligosaccharides_Synthesis_and_Host_Guest_Binding_Property_of_a_Cyclic_Pentasaccharide/6771686
A new
cyclic pentasaccharide comprising an oxymethylene glycosidic
bond connecting the individual α-d-glycopyranoside
monomers is synthesized through cycloglycosylation of a linear pentasaccharide
precursor, which, in turn, is synthesized through the block glycosylation
method. Molecular modeling shows that the 30-membered macrocyclic
pentasaccharide is a distorted ellipsoid structure, with the lower
and upper rims occupied by secondary and primary hydroxyl groups,
respectively. Following the synthesis, the microenvironment of the
cyclic pentasaccharide is assessed through thermodynamic evaluation
upon complexation with 1-aminoadamantane in an aqueous solution, which
shows the formation of ∼1:2 host-to-guest complex and a binding
affinity of 10 500 (±425) M<sup>–1</sup>. Synthesis
and assessment of the host–guest binding property of the new
glycosidic bond expanded cyclic pentasaccharide are presented.
2018-07-06 18:31:15
α- d-glycopyranoside monomers
binding
block glycosylation method
cyclic pentasaccharide
Synthesi
Cyclic
30- membered macrocyclic pentasaccharide
oxymethylene glycosidic bond