640277-82-3

Upstream product

• 16697-49-7 3,4,6-tri-O-benzyl-1,2-O-(methoxyethylidene)-β-D-mannopyranose 
• 346441-51-8 1-O-allyl-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranose 
• 604767-74-0 di-n-butyl (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl) phosphate 
• 1294354-24-7 C₃₂H₄₈O₇Si 
• 1225192-36-8 2-O-acetyl-1-O-allyl-3,4-di-O-benzyl-6-O-triisopropylsilyl-α-D-mannopyranoside 
• 1225192-29-9 C₁₈H₃₆O₇Si 
• 3254-16-8 3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 29073-91-4 1,2-O-(1-methoxyethylidene)-β-D-mannopyranose 
• 129214-38-6 2-O-acetyl-3,4,6-tri-O-benzyl-D-mannopyranoside 
• 915150-33-3 allyl 2-O-benzoyl-3,4-di-O-benzyl-6-O-(triisopropylsilyl)-α-D-mannopyranoside 
• 883878-96-4 3,4-di-O-benzyl-1,2-O-(α-methoxybenzylidene)-6-O-(triisopropylsilyl)-β-D-mannopyranose 
• 108869-64-3 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 

Downstream Products

• 853729-84-7 (2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranosyl trichloroacetimidate 
• 640277-83-4 allyl (3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->6)-2-O-benzoyl-3,4-di-O-benzyl-α-D-mannopyranoside 

Relevant academic research and scientific papers

Synthetic Lipomannan Glycan Microarray Reveals the Importance of α(1,2) Mannose Branching in DC-SIGN Binding

Lipomannan (LM), a glycophospholipid found on the cell surface of mycobacteria, involves the virulence and survival in host cells. However, there is little to no information on how exactly mannan alignment, including the number of mannose units and the br

Toward the Development of the Next Generation of a Rapid Diagnostic Test: Synthesis of Glycophosphatidylinositol (GPI) Analogues of Plasmodium falciparum and Immunological Characterization

A large number of proteins in malaria parasites are anchored using glycophosphatidylinositols (GPIs) with lipid tails. These GPIs are structurally distinct from human GPIs. Plasmodium falciparum GPIs have been considered as potential vaccine candidates be

Synthesis of the essential core of the human glycosylphosphatidylinositol (GPI) anchor

The biological role of GPI anchors is of paramount importance; however, we are still far from fully understanding the structure-function relationship of these molecules. One major limiting factor has been the tiny quantities available from natural sources

Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis

The emergence of multidrug-resistant tuberculosis (TB) and problems with the BCG tuberculosis vaccine to protect humans against TB have prompted investigations into alternative approaches to combat this disease by exploring novel bacterial drug targets and vaccines. Phosphatidylinositol mannosides (PIMs) are biologically important glycoconjugates and represent common essential precursors of more complex mycobacterial cell wall glycolipids including lipomannan (LM), lipoarabinomannan (LAM), and mannan capped lipoarabinomannan (ManLAM). Synthetic PIMs constitute important biochemical tools to elucidate the biosynthesis of this class of molecules, to reveal PIM interactions with host cells, and to investigate the function of PIMs as potential antigens and/or adjuvants for vaccine development. Here, we report the efficient synthesis of all PIMs including phosphatidylinositol (Pl) and phosphatidylinositol mono- to hexa-mannoside (PIM1 to PIM6). Robust synthetic protocols were developed for utilizing bicyclic and tricyclic orthoesters as well as mannosyl phosphates as glycosylating agents. Each synthetic PIM was equipped with a thiol-linker for immobilization on surfaces and carrier proteins for biological and immunological studies. The synthetic PIMs were immobilized on microarray slides to elucidate differences in binding to the dendritic cell specific intercellular adhesion molecule-grabbing nonintegrin (DC-SIGN) receptor. Synthetic PIMs served as immune stimulators during immunization experiments in C57BL/6 mice when coupled to the model antigen keyholelimpet hemocyanin (KLH).

Total synthesis of phosphatidylinositol mannosides of Mycobacterium tuberculosis

The total synthesis of phosphatidylinositol mannosides (PIMs), a key class of antigenic glycolipids found on the cell wall of Mycobacterium tuberculosis, is described. The synthetic strategy relied on a [4 + 3] glycosylation of tetramannoside 1 and pseudo

Assembly of a series of malarial glycosylphosphatidylinositol anchor oligosaccharides

We report an efficient and convergent synthesis of a series of oligosaccharides comprised of the malaria GPI glycan (2 a), a promising anti-malaria vaccine candidate currently in preclinical trials and several related oligosaccharide sequences (3-8) that

A convergent, versatile route to two synthetic conjugate anti-toxin malaria vaccines

The synthesis of two glycosylphosphatidyl inositol (GPI) glycans that constitute the malaria toxin and promising anti-toxin vaccine constructs using a scalable route is described.