1421701-68-9Relevant academic research and scientific papers
In vivo programming of endogenous antibodies via oral administration of adaptor ligands
Nagano, Masanobu,Carrillo, Nancy,Otsubo, Nobumasa,Hakamata, Wataru,Ban, Hitoshi,Fuller, Roberta P.,Bashiruddin, Nasir K.,Barbas, Carlos F.
supporting information, p. 5952 - 5961 (2017/10/10)
Vaccination is a reliable method of prophylaxis and a crucial measure for public health. However, the majority of vaccines cannot be administered orally due to their degradation in the harsh gut environment or inability to cross the GI tract. In this stud
Toward libraries of biotinylated chondroitin sulfate analogues: From synthesis to in vivo studies
Despras, Guillaume,Bernard, Clémence,Perrot, Anthony,Cattiaux, Laurent,Prochiantz, Alain,Lortat-Jacob, Hugues,Mallet, Jean-Maurice
supporting information, p. 531 - 540 (2013/02/25)
Chondroitin sulfate-E (CS-E) oligosaccharidic analogues (di to hexa) were prepared from lactose. In these compounds, the 2-acetamido group was replaced by a hydroxyl group. This modification speeded up the synthesis, and large oligosaccharides were constructed in a few steps from a lactose-originated block. The protecting groups used were as follows; Fmoc for hydroxyl groups to be glycosylated, allyl group for anomeric position protection, and trichoroacetimidate leaving groups were used to prepare up to octasaccharides. We took advantage of the presence of allyl group to develop a click biotinylation, through its transformation into a 3-azido-2-hydroxyl propyl group in two steps (epoxidation and sodium azide epoxide opening). The biotinylating agent was a water-soluble propargylated and biotinylated triethylene glycol (PEG). By using surface plasmon resonance (SPR), it was shown that the di-, tetra-, and hexasaccharides display a binding affinity and selectivity toward HSF/GSF and CXCL12 similar to that of CS-E. A parallel study confirmed their mimicry of natural compounds, based on the hexasaccharide interaction with Otx2, a homeodomain protein involved in brain maturation, thus validating our simplification approach to synthesize bioactive GAG. Copyright
