50826-96-5Relevant academic research and scientific papers
Synthesis of PEGylated lactose analogs for inhibition studies on T.cruzi trans-sialidase
Giorgi, M. Eugenia,Ratier, Laura,Agusti, Rosalia,Frasch, Alberto C. C.,De Lederkremer, Rosa M.
, p. 549 - 559 (2011/12/03)
Trypanosoma cruzi, the agent of Chagas disease, expresses a unique enzyme, the trans-sialidase (TcTS) involved in the transfer of sialic acid from host glycoconjugates to mucins of the parasite. The enzyme is shed to the medium and may affect the immune system of the host. We have previously described that lactose derivatives effectively inhibited the transfer of sialic acid to N-acetyllactosamine. Lactitol also prevented the apoptosis caused by the TcTS, although it is rapidly eliminated from the circulatory system. In this paper we report covalent conjugation of polyethylene glycol (PEG) with lactose, lactobionolactone and benzyl β-D-galactopyranosyl-(1→6)-2-amino-2- deoxy-α-D-glucopyranoside (1) with the hope to improve the bioavailability, though retaining their inhibitory properties. Different conjugation methods have been used and the behavior of the PEGylated products in the TcTS reaction was studied.
One-pot synthesis of β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]-D-GlcNac, a 'core' trisaccharide linked O-glycosidically in glycoproteins of Trypanosoma cruzi
Gallo-Rodriguez, Carola,Varela, Oscar,De Lederkremer, Rosa M.
, p. 163 - 170 (2007/10/03)
Tin(IV) chloride-promoted condensation of benzyl 2-acetamido-3-O- benzoyl-2-deoxy-α-D-glucopyranoside (4) with penta-O-benzoyl-β-D- galactopyranose (6) gave the derivative of β-D-Galp-(1 → 6)-α-D-GlcNAc 7 in 80% yield. This was glycosylated with penta-O-benzoyl-α,β-D- galactofuranose (5), employing the same catalyst, to afford the protected benzyl per-O-benzoyl-β-D-Galf(1 → 4)[β-D-Galp(1 → 6)]D-GlcNAc 10 in 41% yield. Alternatively, compound 10 was obtained directly in a one-pot reaction from 4, by sequential addition of 6 and 5 (34% yield). β-Glycosidic linkages were diastereoselectively formed. De-O-benzoylation of 10, followed by heterogeneous catalytic transfer hydrogenolysis of the benzyl group afforded the free trisaccharide β-D-Galf(1 → 4)[ β-D-Galp(l → 6)]-D-GlcNAc (14) in 98% yield from 10. Sodium borohydride reduction of 14 gave the corresponding alditol, whose spectral data were identical to those reported for the alditol obtained from the 38-43 kDa cell-surface glycoprotein of Trypanosoma cruzi.
