14206-42-9

Basic information

• Product Name: N-(Hydroxyacetyl)-2-O-Methyl-α-neuraMinic Acid
• Synonyms: N-(Hydroxyacetyl)-2-O-Methyl-α-neuraMinic Acid;NFUCYHODBBSMAK-FVESQSFTSA-N
• CAS NO: 14206-42-9
• Molecular Formula: C12H21NO10
• Molecular Weight: 339.29584
• Product Categories: Carbohydrates & Derivatives, Pharmaceuticals, Intermediates & Fine Chemicals
• Mol File: 14206-42-9.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-(Hydroxyacetyl)-2-O-Methyl-α-neuraMinic Acid(CAS DataBase Reference)
• NIST Chemistry Reference: N-(Hydroxyacetyl)-2-O-Methyl-α-neuraMinic Acid(14206-42-9)
• EPA Substance Registry System: N-(Hydroxyacetyl)-2-O-Methyl-α-neuraMinic Acid(14206-42-9)

Safety Data

• Hazardous Substances Data: 14206-42-9(Hazardous Substances Data)

Usage

Uses

N-(Hydroxyacetyl)-2-O-methyl-α-neuraminic Acid is used as a scaffold in study of the binding sites, the siglec (sialic acid binding Ig-lectins) transmembrane receptors, within sialylated glycoconjugates that modulate cellular interactions and signalling events within the immune and nervous systems. Potential for inhibitor design.

Upstream product

• 67670-69-3 N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester 
• 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 
• 6813-81-6 N-acetyl neuraminic acid 
• 73208-80-7 methyl [methyl 4,7,8,9-tetra-O-acetyl-5-acetamido-3,5-dideoxy-α-D-glycero-D-galacto-non-2-ulopyranoside]onate 
• 1454818-67-7 ammonium (methyl 5-amino-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulopyranosid)onate 
• 13831-31-7 Acetoxyacetyl chloride 

Relevant articles and documents

Metal Template Assisted Proximal Arrangement of a Nucleophile and an Electrophile: Site-Selective Acylation of α-Hydroxyamides in Polyols

Site-selective acylation of α-hydroxyl groups in amides has been achieved in the presence of other primary hydroxyl groups with intrinsic high reactivity. In this methodology, a relatively stable pyridine aldoxime ester was exploited as an acyl donor to suppress undesired acylation. The catalytic activation of a pyridine aldoxime ester with a Lewis acid produced a cationic complex, which preferentially attracted the Lewis basic α-hydroxyamide via a template effect, to thus facilitate o-acylation.

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.