1447700-91-5

Upstream product

• 873298-71-6 Benzoic acid (4aR,6S,7R,8S,8aR)-8-hydroxy-2-phenyl-6-p-tolylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester 
• 1219717-79-9 methyl (5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranoside)onate 
• 1219717-81-3 methyl (5-acetamido-7,8,9-tri-O-acetyl-5-N,4-O-carbonyl-2-(dibutylphosphoryl)-3,5-dideoxy-D-glycero-α,β-D-galacto-non-2-ulopyranoside)onate 

Relevant academic research and scientific papers

Synthesis and Evaluation of Liposomal Anti-GM3 Cancer Vaccine Candidates Covalently and Noncovalently Adjuvanted by αgalCer

GM3, a typical tumor-associated carbohydrate antigen, is considered as an important target for cancer vaccine development, but its low immunogenicity limits its application. αGalCer, an iNKT cell agonist, has been employed as an adjuvant via a unique immune mode. Herein, we prepared and investigated two types of antitumor vaccine candidates: (a) self-adjuvanting vaccine GM3-αGalCer by conjugating GM3 with αGalCer and (b) noncovalent vaccine GM3-lipid/αGalCer, in which GM3 is linked with lipid anchor and coassembled with αGalCer. This demonstrated that βGalCer is an exceptionally optimized lipid anchor, which enables the noncovalent vaccine candidate GM3-βGalCer/αGalCer to evoke a comparable antibody level to GM3-αGalCer. However, the antibodies induced by GM3-αGalCer are better at recognition B16F10 cancer cells and more effectively activate the complement system. Our study highlights the importance of vaccine constructs utilizing covalent or noncovalent assembly between αGalCer with carbohydrate antigens and choosing an appropriate lipid anchor for use in noncovalent vaccine formulation.

Highly alpha-selective sialyl phosphate donors for efficient preparation of natural sialosides

A new sialylation reagent that employs an N-acetyl-5-N,4-O-carbonyl protection with dibutyl phosphate as the leaving group has been reported. N-Acetyl neuraminic acid (Neu5Ac) is most frequently found at the terminal end of glycoconjugates on the cell surface. The ring-opening product was obtained as the major product in the hydrolytic step. The one-pot synthetic operation was performed in the presence of NIS/trifluoromethanesulfonic acid (TfOH) promoter system. The sialyl phosphate donor also can be used in an orthogonal one-pot glycosylation, providing an alternative choice for the rapid synthesis of sialosides, allowing the coupling of building blocks independent of their relative reactivities, such as SSEA-4. Sialyl phosphate donors are very efficient at creating complex natural sialosides and are being used for rapid preparation of important sialoside microarrays.