Synthesis of 3-deoxy-3-thio-beta-D-galactopyranosyl (1-4)-beta-D-glucopyranoside as substrate and inhibitor of TcTS

PABLO MORRONE-POZZUTO; MARÍA LAURA UHRIG; ROSALÍA AGUSTÍ

Buenos Aires

Simposio; 3rdArgentinian Symposium on Glycobiology; 2019

T. cruzi trans-sialidase (TcTS) transfer sialic acid from host glycoconjugates to terminal β-D-Galp residues on the parasite mucin-type glycoproteins, generating alpha-Neu5Ac-(2-3)-beta-D-Galp units. TcTS shows two distinct active sites, one for the interaction with the sialic acid (donor site) and the other with the β-D-Galp in acceptor molecule (acceptor site). It represents the only route by which the protozoan can incorporate sialic acid, thus constituting a key target for the chemotherapeutic agents development. Herein we report the synthesis of benzyl 3-deoxy-3-thio-beta-D-galactopyranosyl-(1-4)-β-D-glucopyranoside (compound 1), a lactose analogue with -SH in C-3 of the galactose unit.