3554-93-6

Usage

Uses

Used in Biochemical Research:
BENZYL-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE is used as a substrate for N-acetyl-β-D-glucosaminyltransferase, an enzyme involved in the biosynthesis of various complex carbohydrates. This application is essential for studying the enzyme's function and its role in cellular processes.
Used in Pharmaceutical Industry:
As an inhibitor of 1-β-3-galactotransferase, BENZYL-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE is used to block the apical biosynthetic pathway in polarized HT-29 cells. This inhibition can be valuable in the development of drugs targeting specific cellular pathways, potentially leading to therapeutic applications in various diseases.
Used in Cell Biology:
BENZYL-2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSIDE is used as a research tool to understand the apical biosynthetic pathway in polarized cells, such as HT-29 cells. This knowledge can contribute to the development of targeted therapies for conditions related to cellular polarization and biosynthesis.

InChI:InChI=1/C15H21NO6/c1-9(18)16-12-14(20)13(19)11(7-17)22-15(12)21-8-10-5-3-2-4-6-10/h2-6,11-15,17,19-20H,7-8H2,1H3,(H,16,18)/t11-,12-,13+,14-,15+/m1/s1

Upstream product

• 10375-65-2 benzyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 10375-65-2 Acetic acid (2R,3S,4R,5R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-benzyloxy-tetrahydro-pyran-4-yl ester 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 100-51-6 benzyl alcohol 
• 100-39-0 benzyl bromide 
• 117177-19-2 2-methyl-(1,2-dideoxy-5,6-O-isopropylidene-α-D-glucofurano)-<2,1-d>-2-oxazoline 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 1040191-33-0 N'-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-p-toluenesulfono-hydrazide 
• 3006-60-8 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 62098-31-1 benzyl 3,4,6-tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranoside 
• 4710-88-7 3,4,6-tri-O-acetyl-2-amino-2-deoxy-α-D-glucopyranosyl bromide hydrobromide 

Downstream Products

• 13343-61-8 benzyl 2-acetamido-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 50605-12-4 benzyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside 
• 122351-25-1 benzyl 2-acetamido-2-deoxy-β-D-glucopyranoside 6-(diphenyl phosphate) 
• 87735-36-2 benzyl 2-acetamido-6-bromo-2,6-dideoxy-β-D-glucopyranoside 
• 176167-78-5 benzyl 2-acetamido-3,6-di-O-benzoyl-β-D-allopyranoside 
• 206751-91-9 benzyl 2-acetamido-2-deoxy-3,6-di-O-pivaloyl-β-D-glucopyranoside 
• 139893-41-7 N-[(2R,4aR,6R,7R,8R,8aS)-6-Benzyloxy-8-hydroxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 851189-13-4 benzyl 2-acetamido-6-O-benzoyl-2-deoxy-β-D-glucopyranoside 
• 250734-79-3 Acetic acid (2R,3R,4S,5R,6R)-2-((2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yloxy)-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-81-7 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5S,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-61-3 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,3R,4R,5R,6R)-3-acetylamino-2-benzyloxy-5-hydroxy-6-(4-methoxy-benzyloxymethyl)-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-83-9 Acetic acid (2S,3R,4S,5R,6R)-2-[(2R,3R,4R,6R)-3-acetylamino-2-benzyloxy-6-(4-methoxy-benzyloxymethyl)-5-oxo-tetrahydro-pyran-4-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 250734-77-1 Acetic acid (2R,3R,4S,5R,6R)-2-[(2R,4aR,6R,7R,8R,8aS)-7-acetylamino-6-benzyloxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-4,5-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl ester 
• 206751-95-3 Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-6-benzyloxy-2-benzyloxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-3-yl ester 

Relevant academic research and scientific papers

Synthesis of Bacterial-Derived Peptidoglycan Cross-Linked Fragments

Peptidoglycan (PG) is the core structural motif of the bacterial cell wall. Fragments released from the PG serve as fundamental recognition elements for the immune system. The structure of the PG, however, encompasses a variety of chemical modifications among different bacterial species. Here, the applicability of organic synthetic methods to address this chemical diversity is explored, and the synthesis of cross-linked PG fragments, carrying biologically relevant amino acid modifications and peptide cross-linkages, is presented using solution and solid phase approaches.

Further Insights on Structural Modifications of Muramyl Dipeptides to Study the Human NOD2 Stimulating Activity

A series of muramyl dipeptide (MDP) analogues with structural modifications at the C4 position of MurNAc and on the d-iso-glutamine (isoGln) residue of the peptide part were synthesized. The C4-diversification of MurNAc was conveniently achieved by using CuAAC click strategy to conjugate an azido muramyl dipeptide precursor with structurally diverse alkynes. d-Glutamic acid (Glu), replaced with isoGln, was applied for the structural diversity through esterification or amidation of the carboxylic acid. In total, 26 MDP analogues were synthesized and bio-evaluated for the study of human NOD2 stimulation activity in the innate immune response. Interestingly, MDP derivatives with an ester moiety are found to be more potent than reference compound MDP itself or MDP analogues containing an amide moiety. Among the varied lengths of the alkyl chain in ester derivatives, the MDP analogue bearing the d-glutamate dodecyl (C12) ester moiety showed the best NOD2 stimulation potency.

Monosaccharide inhibitors targeting carbohydrate esterase family 4 de-N-acetylases

The Carbohydrate Esterase family 4 contains virulence factors which modify peptidoglycan and biofilm-related exopolysaccharides. Despite the importance of this family of enzymes, a potent mechanism-based inhibition strategy has yet to emerge. Based on the postulated tridentate binding mode of the tetrahedral de-N-acetylation intermediate, GlcNAc derivatives bearing metal chelating groups at the 2 and 3 positions were synthesized. These scaffolds include 2-C phosphonate, 2-C sulfonamide, 2-thionoacetamide warheads as well as derivatives bearing thiol, amine and azide substitutions at the 3-position. The inhibitors were assayed against a representative peptidoglycan deacetylase, Pgda from Streptococcus pneumonia, and a representative biofilm-related exopolysaccharide deacetylase, PgaB from Escherichia coli. Of the inhibitors evaluated, the 3-thio derivatives showed weak to moderate inhibition of Pgda. The strongest inhibitor was benzyl 2,3-dideoxy-2-thionoacetamide-3-thio-β-D-glucoside, whose inhibitory potency showed an unexpected dependence on metal concentration and was found to have a partial mixed inhibition mode (Ki = 2.9 ± 0.6 μM).

Synthesis and antimicrobial activity of 6-sulfo-6-deoxy-D-glucosamine and its derivatives

6-Sulfo-6-deoxy-D-glucosamine (GlcN6S), 6-sulfo-6-deoxy-D-glucosaminitol (ADGS) and their N-acetyl and methyl ester derivatives have been synthesized and tested as inhibitors of enzymes catalyzing reactions of the UDP-GlcNAc pathway in bacteria and yeasts

Synthesis of lipo-chitooligosaccharide analogues and their interaction with LYR3, a high affinity binding protein for Nod factors and Myc-LCOs

Lipo-chitotetrasaccharide analogues where one central GlcNAc residue was replaced by a triazole unit have been synthesized from a derivative obtained by chitin depolymerization and a functionalized N-acetyl-glucosamine via the copper-catalyzed azide-alkyn

Chemoenzymatic Synthesis of 4-Fluoro-N-Acetylhexosamine Uridine Diphosphate Donors: Chain Terminators in Glycosaminoglycan Synthesis

Unnatural uridine diphosphate (UDP)-sugar donors, UDP-4-deoxy-4-fluoro-N-acetylglucosamine (4FGlcNAc) and UDP-4-deoxy-4-fluoro-N-acetylgalactosamine (4FGalNAc), were prepared using both chemical and chemoenzymatic syntheses relying on N-acetylglucosamine-

Sugar derived alkamine catalytic imine reduction method

The invention discloses a method used for catalytic reduction of imine with saccharide-derivatized amino alcohol. According to the method, imine is taken as a substrate. The method comprises following steps: 1) imine and saccharide-derivatized amino alcohol are dissolved in an organic solvent I, wherein molar ratio of imine to saccharide-derivatized amino alcohol ranges from 100:1-20; 2) trichlorosilane with 1.5 to 5 times equivalent weights is added into a solution obtained via step 1) dropwise, an obtained mixture is stirred and reacted for 12 to 36h at a temperature of -20 to 40 DEG C, and a saturated sodium bicarbonate solution is used for quenching; 3) a material obtained via step 2) is extracted with an organic solvent II, and is subjected to column chromatography isolation so as to obtain amine compounds.

Chemo-enzymatic approach to access diastereopure α-substituted GlcNAc derivatives

The formation of diastereopure α-substituted GlcNAc derivatives in a simple and straightforward way is a challenging task. Herein, we report the chemical synthesis of diastereomeric α/β-substituted GlcNAc derivatives under non-anhydrous atmosphere using u

A robust synthesis of N-glycolyl muramyl dipeptide via azidonitration/reduction

A novel synthetic route leading to N-glycolyl muramyl dipeptide (MDP), a bacterial glycopeptide of particular interest in studies of nucleotide-binding oligomerization domain-containing protein 2 (NOD2), is described. The synthetic strategy hinges on the alkylation of benzylidene-protected glucal with 2-bromopropionic acid and thus circumvents a challenging and non-reproducible SN2 step at the C-3 position of glucosamine derivatives. The subsequent sequence includes an azidonitration and an unusual azide reduction/acylation step via an aza ylide/oxaphospholidine intermediate. This approach generates a protected N-glycolyl MDP that can be either subjected to a one-step global deprotection or differentially deprotected to obtain further derivatives.

Structural analysis of a family 101 glycoside hydrolase in complex with carbohydrates reveals insights into its mechanism

O-Linked glycosylation is one of the most abundant posttranslational modifications of proteins. Within the secretory pathway of higher eukaryotes, the core of these glycans is frequently an N-acetylgalactosamine residue that is α-linked to serine or threo