93253-17-9

Usage

Uses

Used in Biochemistry Research:
BETA-D-GLCNAC-[1->3]-BETA-D-GAL-1->OME is used as a substrate for β-6-GlcNAc-transferase in the preparation of disaccharide mucin fragments. This enzyme is essential for the biosynthesis of mucin-type O-linked glycans, which are crucial for various biological processes, including cell adhesion, immune response, and cell signaling.
Used in Inhibition Studies:
In the field of glycobiology, BETA-D-GLCNAC-[1->3]-BETA-D-GAL-1->OME is used for the inhibition studies of rat lung lectin. This helps researchers understand the binding specificity and interactions between lectins and glycans, which can be useful in developing therapeutic agents targeting glycan-lectin interactions.
Used in Pharmaceutical Industry:
Although not explicitly mentioned in the provided materials, the role of BETA-D-GLCNAC-[1->3]-BETA-D-GAL-1->OME in the biosynthesis of mucin-type O-linked glycans suggests its potential use in the development of drugs targeting glycosylation processes. This could be particularly relevant in the treatment of diseases associated with abnormal glycosylation, such as cancer and inflammatory disorders.

InChI:InChI=1/C15H27NO11/c1-5(19)16-8-11(22)9(20)6(3-17)25-14(8)27-13-10(21)7(4-18)26-15(24-2)12(13)23/h6-15,17-18,20-23H,3-4H2,1-2H3,(H,16,19)

Upstream product

• 93253-16-8 methyl O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-(1-3)-2,4,6-tri-O-benzyl-β-galactopyranosyl 
• 98151-21-4 methyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 3459-18-5 4-nitrophenyl N-acetyl-β-D-glucosaminide 
• 93253-18-0 methyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4,6-tri-O-acetyl-β-D-galactopyranoside 
• 99409-32-2 ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 40010-11-5 methyl 3-O-benzyl-β-D-galactopyranoside 
• 81348-24-5 methyl 2,4,6-tri-O-acetyl-3-O-benzyl-β-D-galactopyranoside 
• 19464-78-9 methyl 2,4,6-tri-O-acetyl-β-D-galactopyranoside 
• 210472-13-2 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-6-((2R,3S,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy)-5-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-4-yl ester 
• 93274-52-3 methyl 3-O-allyl-β-D-galactopyranoside 
• 55697-53-5 methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 93253-15-7 methyl 3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-2,4,6-tri-O-benzyl-β-D-galactopyranoside 
• 134308-33-1 2-methyl-(2-acetamido-3,4,6-tri-O-acetyl-1,2-dideoxy-β-D-glucopyrano)-<2,1-d>-2-oxazoline 

Relevant academic research and scientific papers

Novel features of acceptor recognition by β-(1 ← 4)- galactosyltransferase

In order to understand how β-(1→4)-galactosyltransferase recognizes its glycosyl acceptor, substrate specificities were investigated using synthetic 2-acetamido-2-deoxy-D-glucopyranose (N-acetylglucosamine) derivatives in which the 1-, 2-, 3-, 4-, and 6-p

Enzymic synthesis of HexNAc-containing disaccharide glycosides.

The following disaccharide glycosides were obtained from the appropriate donor and acceptor glycosides by employing glycosidases from the mollusc Chamelea gallina as catalysts: alpha-D-Galp-OMe (N-acetyl-alpha-D- galactosaminidase), beta-D-GalpNAc-(1----3)-beta-D-Galp-OMe, beta-D-GlcpNAc-(1----3)-beta-D-Galp-OMe, and beta-D-GlcpNAc-(1----6)-alpha-D-Manp-OMe (N-acetyl-beta-D-hexosaminidase). The regioselectivity of the N-acetyl-beta-D-hexosaminidase-catalysed reactions depended on the anomeric configuration of the acceptor. Thus, alpha-D-Galp-OMe gave beta-D-GlcpNAc- (1----6)-alpha-D-Galp-OMe almost exclusively, whereas beta-D-Galp-OMe gave beta-D-GlcpNAc-(1----3)-beta-D-Galp-OMe and beta-D-GlcpNAc-(1----6)-beta-D-Galp-OMe in almost equal amounts. The isolation of the products by chromatography was straightforward.

SYNTHESIS OF DI-, TRI-, AND TETRA-SACCHARIDES CORRESPONDING TO RECEPTOR STRUCTURES RECOGNISED BY Streptococcus pneumoniae

Syntheses are described for methyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-α-D-glucopyranoside, methyl 2-acetamido-2-deoxy-4-O-β-D-galactopyranosyl-β-D-glucopyranoside, methyl 3-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-β-D-galactopyranoside, methyl

SYNTHETIC MUCIN FRAGMENTS: METHYL 3-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-β-D-GALACTOPYRANOSYDE AND METHYL 3-O-(2-ACETAMIDO-2-DEOXY-3-O-β-D-GALACTOPYRANOSYL-β-D-GLUCOPYRANOSYL)-β-D-GALACTOPYRANOSIDE

Methyl 2,4,6-tri-O-benzyl-β-D-galactopyranoside (5) was obtained crystalline by way of its 3-O-allyl derivative, which was in turn obtained by ring-opening of a presumed 3,4-O-stannylene derivative of methyl β-D-galactopyranoside, followed by benzylation.