67670-69-3

Usage

Uses

Used in Pharmaceutical Industry:
N-ACETYL-2-CHLORO-2-DEOXYNEURAMINIC ACID METHYL ESTER 4,7,8,9-TETRAACETATE is used as an intermediate for the synthesis of neuraminic acid derivatives, which are essential components of glycoproteins. These derivatives play a crucial role in various biological processes, making them important targets for drug development.
Used in Chemical Synthesis:
N-ACETYL-2-CHLORO-2-DEOXYNEURAMINIC ACID METHYL ESTER 4,7,8,9-TETRAACETATE is used as a versatile intermediate in the preparation of various neuraminic acid derivatives. Its unique chemical properties allow for the development of a wide range of compounds with potential applications in different industries, including pharmaceuticals, diagnostics, and research.
Used in Research and Development:
N-ACETYL-2-CHLORO-2-DEOXYNEURAMINIC ACID METHYL ESTER 4,7,8,9-TETRAACETATE is used as a key compound in research and development for the study of glycoproteins and their role in various biological processes. Its unique structure and properties make it an essential tool for understanding the function and regulation of these complex molecules.

InChI:InChI=1/C20H28ClNO12/c1-9(23)22-16-14(31-11(3)25)7-20(21,19(28)29-6)34-18(16)17(33-13(5)27)15(32-12(4)26)8-30-10(2)24/h14-18H,7-8H2,1-6H3,(H,22,23)/t14-,15+,16+,17+,18+,20-/m0/s1

Upstream product

• 108740-39-2 (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 
• 6931-68-6 methyl (5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-α-D-galacto-2-nonulopyranosid)onate 
• 67-56-1 methanol 
• 108-24-7 acetic anhydride 
• 19342-33-7 N-acetyl neuraminic acid 
• 20298-35-5 N-acetylneuraminic acid methyl ester 
• 75-36-5 acetyl chloride 
• 22900-11-4 (2R,3R,4S)-3-acetamido-4-hydroxy-2-((1R,2R)-1,2,3-trihydroxypropyl)-3,4-dihydro-2H-pyran-6-carboxylic acid 
• 108740-39-2 methyl 2,4,7,8,9-penta-O-acetyl-5-(acetylamino)-3,5-dideoxy-β-L-glycero-L-altro-2-nonulopyranosidonate 
• 6931-68-6 (4S,5R,6R)-2,4-Diacetoxy-5-acetylamino-6-((1S,2S)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 489-46-3 sialic acid 
• 1204315-23-0 (4S,5R,6R)-5-Acetylamino-2,4-dihydroxy-6-((1S,2S)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 108740-37-0 methyl 2,4,7,8,9-penta-O-acetyl-5-(acetylamino)-3,5-dideoxy-β-D-glycero-L-altro-2-nonulopyranosidonate 
• 119241-60-0 5-acetamido-D-glycero-D-galacto-2-nonulosonic acid methyl ester 

Downstream Products

• 128678-37-5 Methyl (3-methoxyphenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 59694-37-0 methyl (4-nitrophenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-oxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 128678-36-4 Methyl (phenyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-2-nonulopyranosid)onate 
• 90124-28-0 Methyl-6-O-(4,7,8,9-tetra-O-acetyl-5-acetylamino-3,5-didesoxy-D-glycero-β-D-galakto-2-nonulopyranosidonsaeure-methylester)-2,3,4-tri-O-benzyl-β-D-glucopyranosid 
• 90124-29-1 methyl [methyl(5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranosyl)onate]-(2→6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside 
• 90124-30-4 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 109681-25-6 methyl O--(2->6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside 
• 73960-72-2 methyl-2,3-didehydro-4,7,8,9-tetra-O-acetyl-N-acetylneuraminate 
• 82703-91-1 Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-D-glycero-α-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid 
• 82703-92-2 methyl 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-2-O-salicyoyl-D-galacto-2-nonulopyranoside 
• 82703-90-0 (2S,4S,5R,6R)-5-Acetylamino-4-hydroxy-2-((2R,3R,4S,5R)-3,4,5,6-tetrahydroxy-tetrahydro-pyran-2-ylmethoxy)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 
• 89733-59-5 Benzyl-2,3,4-tri-O-benzyl-6-O-(methyl-5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-didesoxy-β-D-glycero-D-galacto-2-nonulopyranosylonat)-β-D-galactopyranosid 
• 127218-72-8 2-(trimethylsilyl)ethyl O--(2->6)-β-D-galactopyranoside 
• 125884-24-4 2-(trimethylsilyl)ethyl O--(2->6)-β-D-galactopyranoside 

Relevant academic research and scientific papers

Synthesis of Oligomers Derived from Amide-Linked Neuraminic Acid Analogues

N-Fluoren-9-ylmethoxycarbonyl-protected sugar amino acids derived from α-O-methoxy- and 2,3-dehydroneuraminic acids have been prepared. Incorporation of these monomer units into solid-phase synthesis led to the efficient synthesis of two series of oligomers varying from one to eight units in length. The (1-5)-linked amides of 2,3-dehydroneuraminic acid were further subjected to hydrogenation giving a third series of oligomers with a β-hydrido substituent at the anomeric carbon.

Sialated diazeniumdiolate: A new sialidase-activated nitric oxide donor

(Chemical Equation Presented) A new sialated diazeniumdiolate has been synthesized, and the glycosylation product was exclusively an α anomer. This new nitric oxide donor exhibited significantly improved stability as compared to its parent diazeniumdiolate salts, and it could be efficiently hydrolyzed by neuraminidase to release nitric oxide with a Km of 0.14 mM. The sialic acid-NO conjugate would be a valuable prodrug that targets NO to influenza viruses.

Characterization of a high-affinity sialic acid-specific CBM40 from Clostridium perfringens and engineering of a divalent form

CBMs(carbohydrate-binding modules) are a class of polypeptides usually associated with carbohydrate-active enzymatic sites. We have characterized a new member of the CBM40 family, coded from a section of the gene NanI from Clostridium perfringens. Glycan arrays revealed its preference towards α(2,3)-linked sialosides, which was confirmed and quantified by calorimetric studies. The CBM40 binds to α(2,3)-sialyl-lactose with a Kd of -30 μM, the highest affinity value for this class of proteins. Inspired by lectins' structure and their arrangement as multimeric proteins, we have engineered a dimeric form of the CBM, and using SPR (surface plasmon resonance) we have observed 6-11- fold binding increases due to the avidity affect. The structures of the CBM, resolved by X-ray crystallography, in complex with α(2,3)- or α(2,6)-sialyl-lactose explain its binding specificity and unusually strong binding.

Synthesis and Biological Evaluation of Several Dephosphonated Analogues of CMP-Neu5Ac as Inhibitors of GM3-Synthase

Previous studies demonstrated that reducing the GM3 content in myoblasts increased the cell resistance to hypoxic stress, suggesting that a pharmacological inhibition of the GM3 synthesis could be instrumental for the development of new treatments for ischemic diseases. Herein, the synthesis of several dephosphonated CMP-Neu5Ac congeners and their anti-GM3-synthase activity is reported. Biological activity testes revealed that some inhibitors almost completely blocked the GM3-synthase activity in vitro and reduced the GM3 content in living embryonic kidney 293A cells, eventually activating the epidermal growth factor receptor (EGFR) signaling cascade.

Investigation of protecting group for sialic acid carboxy moiety toward sialylglycopeptide synthesis by the TFA-labile protection strategy

The sialylation using sialyl donor with 2,6-dimethylbenzyl (DMBn) ester at C-1 carboxy group rapidly proceeded with good α-selectivity to yield sialyl-N-acetylgalactosaminylated 9-fluorenylmethoxycarbonyl (Fmoc) serine unit. The unit was used for the solid-phase peptide synthesis (SPPS) of the sialyl glycopeptide. The DMBn group was removed during the final deprotection by the trifluoroacetic acid (TFA) treatment keeping the sialyl bond intact and the desired sialyl glycopeptide was successfully obtained. This protecting group strategy provided easier access to sialyl glycoamino acids for sialyl glycopeptides synthesis.

Donor-Reactivity-Controlled Sialylation Reactions

Although tremendous efforts have been made for the efficient preparation of sialosides, controlling the stereochemical outcome of sialylation reaction still remains one of the most challenging tasks due to the unique chemical structure of sialic acid. We developed a new strategy to statistically analyze the stereoselectivity of sialylation reactions on six types of p-tolyl thiosialosides in NIS/TfOH system using Relative Reactivity Value (RRV) as the indicator. Analysis of the reaction mechanism showed the formation of the relatively stable glycosyl bromide and glycosyl chloride intermediates from halide- and triflate-containing promotors in the absence of an acceptor. We found that the α/β-stereoselectivity, yields, and intermediate changes were associated with their donor reactivity. These findings enable to tailor the most suitable building blocks for stereo-controlled sialylation reactions.

One pot synthesis of thio -glycosides via aziridine opening reactions

A one-pot aziridine opening reaction by glycosyl thiols generated in situ from the corresponding anomeric thio-acetates affords thio-glycosides with a pseudo-disaccharide structure and an N-linked tether. The scope of the one-pot aziridine opening reaction was explored on a series of mono- and disaccharides, creating a class of pseudo-glycosidic compounds with potential for further functionalization. Unexpected anomerization of glycosyl thiols was observed under the reaction conditions and the influence of temperature, base and solvent on the isomerization was investigated. Single isomers were obtained in good to acceptable yields for mannose, rhamnose and sialic acid derivatives. The class of thio-glycomimetics synthesized can potentially be recognized by various lectins, while presenting hydrolytic and enzymatic stability. The nitrogen functionality incorporated in the glycomimetics can be exploited for further functionalization, including tethering to linkers, scaffolds or peptide residues.

MATERIALS AND METHODS FOR THE PREPARATION OF BACTERIAL CAPSULAR POLYSACCHARIDES

Methods for preparing saccharide products such as bacterial capsular polysaccharides are provided. The methods include: forming a reaction mixture containing one or more bacterial capsular polysaccharide synthases, a sugar acceptor, and one or more sugar

Differential recognition of diet-derived Neu5Gc-Neoantigens on glycan microarrays by carbohydrate-specific pooled human IgG and IgA antibodies

Sialic acids (Sias) cover vertebrate cell surface glycans. N-Acetylneuraminic acid (Neu5Ac) and its hydroxylated form N-glycolylneuraminic acid (Neu5Gc) are common Sia in mammals. Humans cannot synthesize Neu5Gc but accumulate it on cells through red-meat rich diets, generating numerous immunogenic Neu5Gc-neoantigens. Consequently, humans have diverse anti-Neu5Gc antibodies affecting xenotransplantation, cancer, atherosclerosis, and infertility. Anti-Neu5Gc antibodies circulate as IgG, IgM, and IgA isotypes; however, repertoires of the different isotypes in a large population have not been studied yet. Here, we used glycan microarrays to investigate anti-Neu5Gc IgGs and IgAs in intravenous immunoglobulin (IVIG) or pooled human IgA, respectively. Binding patterns on microarrays fabricated with Neu5Gc- and Neu5Ac-glycans, together with inhibition assays, revealed that different IVIG preparations have highly specific anti-Neu5Gc IgG reactivity with closely related repertoires, while IgAs show cross-reactivity against several Neu5Ac-glycans. Such different anti-Neu5Gc IgG/IgA repertoires in individuals could possibly mediate distinctive effects on human diseases.

Synthesis of neuraminidase-resistant sialoside-modified three-way junction DNA and its binding ability to various influenza viruses

Natural sialic acid-modified compounds are capable of targeting influenza virus hemagglutinin (HA). However, these compounds have limited inhibitory effect because natural O-glycoside bond in these compounds are prone to be cleaved by neuraminidase (NA) on the surface of viruses. In this study, we synthesized NA-resistant sialoside that included unnatural S-glycoside bonds and modified this sialoside on a three-way junction (3WJ) DNA to display complementary distribution to its binding sites on a HA trimer. This S-glycoside-containing sialoside-modified 3WJ DNA showed certain NA resistance and maintained high binding affinity. Importantly, our observations showed that substituting natural O-glycoside with unnatural S-glycoside did not affect the binding affinity of the sialoside-modified 3WJ DNA for viruses. Thus, this study is an important step forward in the development of NA-resistant sialoside derivatives for more effective detection and inhibition of infection by a broad spectrum of viruses.