93221-21-7

Usage

Uses

Used in Biochemistry and Molecular Biology:
2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate is used as a reagent for the labeling and detection of glycoproteins, enabling researchers to study and analyze these proteins in various biological processes. Its application is crucial for understanding cell signaling, protein function, and disease mechanisms where glycoproteins play a significant role.
Used in Pharmaceutical Research and Drug Development:
In the pharmaceutical industry, 2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl isothiocyanate is utilized for its potential in the development of new drugs. Its unique chemical properties allow it to be explored for the creation of therapeutic agents that could target glycoproteins involved in different diseases, thereby offering novel treatment options.

Upstream product

• 572-09-8 2,3,4,6-tetra-O-acetyl-D-mannopyranosyl bromide 
• 333-20-0 potassium thioacyanate 
• 3068-32-4 1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside 
• 2290-65-5 trimethylsilyl isothiocyanate 
• 83-87-4 penta-O-acetyl-α-D-galactopyranose 
• 572-09-8 acetobromogalactose 
• 3068-32-4 1-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose 
• 25878-60-8 D-galactose pentaacetate 
• 592-87-0 lead(II) thiocyanate 
• 4163-60-4 β-D-galactose peracetate 
• 943860-86-4 2-methyl-4,5-dihydro-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-galactopyrano)[2,1-d]-2-oxazoline 
• 463-71-8 thiophosgene 
• 572-10-1 2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl chloride 
• 4163-65-9 per-O-acetyl-α-D-mannopyranose 

Downstream Products

• 1174340-48-7 N-[(1R,2R)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-thiourea 
• 1174340-47-6 N-[(1S,2S)-2-aminocyclohexyl]-N'-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-thiourea 
• 1444827-56-8 5-benzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-58-0 5-p-nitrobenzoyl-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-59-1 5-(4-methylbenzoyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-60-4 5-(4-cyanobenzoyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-64-8 5-(adamantane-1-carbonyl)-2-((2,3,4,6-tetra-O-acetyl-α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-69-3 5-p-nitrobenzoyl-2-((α-D-mannopyranos-1-yl)amino)thiazole 
• 1444827-71-7 5-(4-cyanobenzoyl)-2-((α-D-mannopyranos-1-yl)amino)thiazole 
• 77489-39-5 2,3,4,6-tetra-O-acetyl-1-N--β-D-galactopyranosylamine 
• 263762-44-3 1N-(tert-butoxycarbonyl-6-aminohexanoyl)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylamine 
• 108275-84-9 5-(p-bromophenyl)-2-(β-D-galactopyranosylamino)thiazole 
• 108275-81-6 5-(p-bromophenyl)-2-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosylamino)thiazole 

Relevant academic research and scientific papers

Facile control of the self-assembled structures of polylysines having pendent mannose groups via pH and surfactant

A mannose-modified polylysine was synthesized, the self-assembly of which in aqueous solution led to the formation of spherical micelles, vesicles and rod-like micelles in a controlled manner by simply changing the solution pH and adding a surfactant to the solution.

Synthesis and Antimicrobial Activities of 1,2,4-Thiadiazolidin-3-thione Hydrochlorides

Synthesis of N-glucosyl/lactosyl/maltosyl-1,2,4-thiadizolidin-3-thione hydrochlorides by the reaction of N-phenyl-S-chloroisothiocarbamoyl chloride and N-glucosyl/lactosyl/maltosyl thiocarbamides is reported. The simple isolation method with good yields under mild condition is applicable for the present protocol. All the newly synthesized thiadiazolidin-3-thiones exhibit moderate to good antimicrobial activities against a variety of pathogen

Synthesis of some new carbohydrate-containing thiouriedonaphtho-quinones

Abstract New alkyl, aryl, and glycosylthiouriedo derivatives of 2,3-diamino-1,4-naphthoquinone were synthesized via the reaction of isothiocyanates with 2,3-diamino-1,4-naphthoquinone. The new compounds were fully characterized through their physicochemical properties.

Gold nanoparticles decorated by clustered multivalent cone-glycocalixarenes actively improve the targeting efficiency toward cancer cells

A novel approach for multivalent targeting by using gold nanoparticles noncovalently decorated by tight functionalization with a cone-glycocalixarene bearing four mannose units is reported. The targeting efficiency of these multivalent nanoparticles is shown to be remarkably improved compared to that of nanoparticles bearing a monovalent mannosylated derivative. This journal is the Partner Organisations 2014.

Thiazolylaminomannosides as potent antiadhesives of type 1 piliated escherichia coli isolated from crohn's disease patients

Adherent-invasive Escherichia coli (AIEC) have previously been shown to induce gut inflammation in patients with Crohn's disease (CD). We developed a set of mannosides to prevent AIEC attachment to the gut by blocking the FimH bacterial adhesin. The crystal structure of the FimH lectin domain in complex with a lead thiazolylaminomannoside highlighted the preferential position for pharmacomodulations. A small library of analogues showing nanomolar affinity for FimH was then developed. Notably, AIEC attachment to intestinal cells was efficiently prevented by the most active compound and at around 10000-fold and 100-fold lower concentrations than mannose and the potent FimH inhibitor heptylmannoside, respectively. An ex vivo assay performed on the colonic tissue of a transgenic mouse model of CD confirmed this antiadhesive potential. Given the key role of AIEC in the chronic intestinal inflammation of CD patients, these results suggest a potential antiadhesive treatment with the FimH inhibitors developed.

Design and synthesis of thiourea compounds that inhibit transmembrane anchored carbonic anhydrases

A library of 32 novel glycoconjugate thiourea-bridged benzene sulfonamides have been synthesized from the reaction of glycosyl isothiocyanates with a panel of simple benzene sulfonamides comprising either a free amine or hydrazide. All compounds were inve

Comparative study of microwave induced and conventional synthesis of acetylated sugar isothiocyanates and related thiocarbamides

The synthesis of several acetylated sugar isothiocyanates have been carried out under microwave irradiation in excellent yields of products by using related bromides and lead thiocyanate in sodium dried xylene. Several acetylated sugar thiocarbamides have been synthesized by the interaction of respective acetylated sugar isothiocyanates with appropriate aryl amines under microwave irradiation. Copyright E-Journal of Chemistry 2004-2011.

Synthesis and antimicrobial studies of some bis-glycosyl isodithiobiurets

Certain 2-S-tetra-O-benzoyl-D-glucopyranosyl-1-aryl-5-tetra-Oacetyl-β-D- galactopyranosyl-2, 4- isodithiobiurets have been synthesized by the interaction of tetra-O-acetyl-β-D-galactopyranosyl isothiocyante and various S- tetra-O-benzoyl-D- glucopyranosyl-1-aryl isothiocarbamides. The newly synthesized compounds were screened for their antimicrobial activities.

A novel, simple cyclocondensation reaction towards glycosyl triazines

Sugars bearing an isothiocyanate moiety at C-1 react with diazadienium iodide to afford glycosyl triazines that represent, through an easy cyclocondensation reaction step, a flexible entry to different nucleoside analogues. We herein demonstrate that this [4+2] cycloaddition reaction occurs with total regiocontrol and good yields. Subsequent transformation of the thiocarbonyl into a carbonyl, and nucleophilic substitution of the methylsulfanyl group by ammonia, yields the 5-azacytidine analogues. All compounds were fully characterised by IR, HRMS, and 13C and 1H NMR (COSY, HMBC and HMQC). Georg Thieme Verlag.

New N-galactosides: Synthesis of N-galactosylated thiocarbamides, benzothiazolyl thiocarbamides and thiocarbamates

The title compounds were prepared by the condensation of tetra-O-acetyl-β-D-galactopyranosyl isothiocyanate with several amines, 2-aminobenzothiazole/substituted benzothiazoles and alcohols respectively. The structure of these new N-galactoside has been established on the basis of usual chemical transformations and IR, NMR and Mass spectral studies of some typical cases.