223123-44-2Relevant academic research and scientific papers
Synthesis and affinities of C3-symmetric thioglycoside-containing trimannosides
Bi, Jingjing,Zhao, Chuanfang,Cui, Wei,Zhang, Chaoli,Shan, Qiuli,Du, Yuguo
, p. 56 - 65 (2015)
Thioglycoside-containing trimannose analogs were designed and prepared to mimic the natural N-glycan core trisaccharide α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man. (1→6)-S-Linked trimannoside 1 and its trivalent cluster 2 were synthesized in 11 and 15 steps, respectively, taking advantages of the armed mannopyranosyl trichloroacetimidate as glycosyl donor. Hemagglutination inhibition of the two new thiomannotriose analogs was preliminarily examined. Comparing to the parent trimannoside α-d-Man-(1→3)-[α-d-Man-(1→6)]-d-Man-OMe, the cluster mannotrioside 2 presented a comparable binding affinity to Con A, while the monomer 6-S-trimannoside 1 exhibited a slightly lower inhibition ability.
Syntheses of mannopyranoside 6-thiophosphate and 6-deoxy-6-thio-mannopyranoside phosphate as ligands for affinity chromatography
Kopitzki, Sebastian,Thiem, Joachim
, p. 7 - 11 (2019)
Direct 6-thiophosphorylation of mannopyranoside gave both the wanted S- as well as the undesired O-phosphates. This required sequential protecting group syntheses to give mannopyranoside6-phosphate and 6-thiophosphate as well as 6-deoxy-6-thio-mannopyrano
Synthesis of sialyl Lewis x mimetics as selectin inhibitors by enzymatic aldol condensation reactions
Lin, Chun-Cheng,Moris-Varas, Francisco,Weitz-Schmidt, Gabriel,Wong, Chi-Huey
, p. 425 - 433 (2007/10/03)
Several D-mannosyl phosphate/phosphonate derivatives have been enzymatically prepared as sialyl Lewis x tetrasaccharide mimics, which showed strong-to-moderate inhibition against E-, P-, and L-selectins. The synthesis of these mimics is very straightforward; mannosyl aldehyde derivatives are condensed with dihydroxyacetone phosphate (DHAP) in the presence of a DHAP-dependent aldolase to provide mannosyl phosphates. Copyright (C) 1999 Elsevier Science Ltd.
