140428-83-7

Basic information

• Product Name: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• Synonyms: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside
• CAS NO: 140428-83-7
• Molecular Weight: 417.373
• Mol File: 140428-83-7.mol
• Article Data: 44

Chemical Properties

• CAS DataBase Reference: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(140428-83-7)
• EPA Substance Registry System: 2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside(140428-83-7)

Safety Data

• Hazardous Substances Data: 140428-83-7(Hazardous Substances Data)

Usage

Chemical compound

2-azidoethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

Potential usage

Glycobiology and carbohydrate chemistry

Function

Glycosylation reagent for synthesis of complex carbohydrates and glycoconjugates

Modification

Modified form of α-D-mannopyranoside with four acetyl groups and an azidoethyl group

Selective modification

Functional groups allow for selective modification of sugar molecule

Applications

Used in synthesis of glycoconjugates for research and medical applications, including vaccine development and drug delivery systems

Bioorthogonal chemistry

Azido group can be utilized in bioorthogonal chemistry and click chemistry reactions

Labeling and visualization

Azido group can be used for labeling and visualization of glycans in biological systems

Upstream product

• 83-87-4 D-Mannose pentaacetate 
• 1517-05-1 2-azidoethanol 
• 121238-27-5 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate 
• 57884-82-9 2,3,4,6-tetra-O-acetyl-β-D-mannopyranose 
• 7322-31-8 β-D-mannose 
• 252210-04-1 (3-azidopropyl) 2,3,4,6-tetra-O-acetate-α-D-mannopyranoside 
• 7296-15-3 alpha-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 
• 540-51-2 2-bromoethanol 
• 849420-02-6 (2-chloroethyl)-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-D-mannopyranose 
• 617691-71-1 2'-hydroxyethyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside 
• 13242-53-0 acetobromomannose 

Downstream Products

• 338796-43-3 2-tert-butyloxycarbonylamidoethyl 6-O-(toluene-4-sulfonyl)-α-D-mannopyranoside 
• 1384873-15-7 C₅₀H₆₀N₈O₂₂ 
• 1384873-19-1 C₄₅H₅₃N₅O₂₁ 
• 1384873-23-7 C₆₆H₇₆N₁₀O₂₄ 
• 1384873-12-4 C₃₁H₃₅N₅O₁₂ 
• 1616972-76-9 C₁₂₀H₁₈₆N₃₀O₆₆ 
• 1616972-77-0 C₁₂₃H₁₉₂N₃₀O₆₉ 
• 1592594-67-6 C₂₄H₃₀N₄O₁₀ 

Relevant articles and documents

One-pot synthesis of multivalent arrays of mannose mono- and disaccharides

The synthesis of a selection of multivalent arrays of mannose mono- and disaccharides, that are of potential use as anti-infective agents against enterobacteria infections, is described.

Trivalent α-D-mannoside clusters as inhibitors of type-1 fimbriae-mediated adhesion of Escherichia coli: Structural variation and biotinylation

Structural modifications of trivalent cluster mannosides are presented to further elucidate the ligand preferences of the type-1 fimbrial lectin of Escherichia coli. Two types of variations are performed, either regarding the aglycone part of cluster mann

Thiosugar naphthalene diimide conjugates: G-quadruplex ligands with antiparasitic and anticancer activity

Glycosyl conjugation to drugs is a strategy being used to take advantage of glucose transporters (GLUT) overexpression in cancer cells in comparison with non-cancerous cells. Its extension to the conjugation of drugs to thiosugars tries to exploit their higher biostability when compared to O-glycosides. Here, we have synthesized a series of thiosugar naphthalene diimide conjugates as G-quadruplex ligands and have explored modifications of the amino sidechain comparing dimethyl amino and morpholino groups. Then, we studied their antiproliferative activity in colon cancer cells, and their antiparasitic activity in T. brucei and L. major parasites, together with their ability to bind quadruplexes and their cellular uptake and location. We observed higher toxicity for the sugar-NDI-NMe2 derivatives than for the sugar-NDI-morph compounds, both in mammalian cells and in parasites. Our experiments indicate that a less efficient binding to quadruplexes and a worse cellular uptake of the carb-NDI-morph derivatives could be the reasons for these differences. We found small variations in cytotoxicity between O-carb-NDIs and S-carb-NDIs, except against non-cancerous human fibroblasts MRC-5, where thiosugar-NDIs tend to be less toxic. This leads to a notable selectivity for β-thiomaltosyl-NDI-NMe2 12 (9.8 fold), with an IC50 of 0.3 μM against HT-29 cells. Finally, the antiparasitic activity observed for the carb-NDI-NMe2 derivatives against T. brucei was in the nanomolar range with a good selectivity index in the range of 30- to 69- fold.

Prophylactic Antiviral Activity of Sulfated Glycomimetic Oligomers and Polymers

In this work, we investigate the potential of highly sulfated synthetic glycomimetics to act as inhibitors of viral binding/infection. Our results indicate that both long-chain glycopolymers and short-chain glycooligomers are capable of preventing viral infection. Notably, glycopolymers efficiently inhibit Human Papillomavirus (HPV16) infection in vitro and maintain their antiviral activity in vivo, while the glycooligomers exert their inhibitory function post attachment of viruses to cells. Moreover, when we tested the potential for broader activity against several other human pathogenic viruses, we observed broad-spectrum antiviral activity of these compounds beyond our initial assumptions. While the compounds tested displayed a range of antiviral efficacies, viruses with rather diverse glycan specificities such as Herpes Simplex Virus (HSV), Influenza A Virus (IAV), and Merkel Cell Polyomavirus (MCPyV) could be targeted. This opens new opportunities to develop broadly active glycomimetic inhibitors of viral entry and infection.