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Chemical Properties

White Powder

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-/m0/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 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 99409-32-2 ethyl-3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-1-thio-β-D-glucopyranoside 
• 80035-31-0 benzyl 2-phthalimido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 22314-39-2 (2R,3S,4R,5R,6R)-5-Amino-6-benzyloxy-2-hydroxymethyl-tetrahydro-pyran-3,4-diol 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 

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 
• 41355-95-7 benzyl 2-acetamido-2-deoxy-β-D-galactopyranoside 
• 206751-92-0 benzyl 2-acetamido-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside 
• 461025-95-6 benzyl 2-acetamido-6-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 461025-94-5 benzyl 2-acetamido-6-O-acetyl-2-deoxy-3,4-isopropylidene-β-D-galactopyranoside 
• 461025-98-9 benzyl 2-acetamido-4,6-di-O-acetyl-2-deoxy-β-D-galactopyranoside 
• 461025-96-7 benzyl 2-acetamido-6-O-acetyl-2-deoxy-3-O-tert-butyldimethylsilyl-β-D-galactopyranoside 

Relevant academic research and scientific papers

Regioselective Manipulation of GlcNAc Provides Allosamine, Lividosamine, and Related Compounds

Palladium-catalyzed oxidation of isopropyl N-acetyl-α-d-glucosamine (GlcNAc) is used to prepare the rare sugars allosamine, lividosamine, and related compounds with unprecedented selectivity. The Passerini reaction applied on 3-keto-GlcNAc provides an ent

Synthesis of β(1-4)-Linked Disaccharides of N-Acetylglucosamine and3 N-Acetylmuramic Acid by Their Direct Condensation

As a basic study in the synthetic approach to immunoactive cell wall peptid3oglycan whose backbone is a β(1-4)-linked saccharide of alternating glucosamine and3 muramic acid, methods for the direct condensation of these sugar components were studied and O-(N-acetyl-β-muramyl)-(1->4)-N-acetyl-D-glucosamine and O-(N-acetyl-β-D-glucosaminyl)-(1->4)-N-acetylmuramic acid were synthesized.In the synthesis of the latter disaccharide, previous formation of an ester bond between the carboxyl group of muramic acid and the 6-hydroxyl group of glucosamine proved to facilitate the glycoside bond formation between these sugar moieties.

Membrane Association Dictates Ligand Specificity for the Innate Immune Receptor NOD2

The human gut must regulate its immune response to resident and pathogenic bacteria, numbering in the trillions. The peptidoglycan component of the bacterial cell wall is a dense and rigid structure that consists of polymeric carbohydrates and highly cross-linked peptides which offers protection from the host and surrounding environment. Nucleotide-binding oligomerization domain-containing protein 2 (NOD2), a human membrane-associated innate immune receptor found in the gut epithelium and mutated in an estimated 30% of Crohn's disease patients, binds to peptidoglycan fragments and initiates an immune response. Using a combination of chemical synthesis, advanced analytical assays, and protein biochemistry, we tested the binding of a variety of synthetic peptidoglycan fragments to wild-type (WT)-NOD2. Only when the protein was presented in the native membrane did binding measurements correlate with a NOD2-dependent nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) response, supporting the hypothesis that the native-membrane environment confers ligand specificity to the NOD2 receptor for NF-κB signaling. While N-acetyl-muramyl dipeptide (MDP) has been thought to be the minimal peptidoglycan fragment necessary to activate a NOD2-dependent immune response, we found that fragments with and without the dipeptide moiety are capable of binding and activating a NOD2-dependent NF-κB response, suggesting that the carbohydrate moiety of the peptidoglycan fragments is the minimal functional epitope. This work highlights the necessity of studying NOD2-ligand binding in systems that resemble the receptor's natural environment, as the cellular membrane and/or NOD2 interacting partners appear to play a crucial role in ligand binding and in triggering an innate immune response.

Anti-cancer properties and catalytic oxidation of sulfides based on vanadium(V) complexes of unprotected sugar-based Schiff-base ligands

In this article, benzyl 2-deoxy-2-salicylideneamino-α-D-glucopyranoside (H2SalHGlc), a sugar-based Schiff-base ligand, as well as four of its derivatives including H2Sal5-BrGlc, H2Sal3,5-tBu/sup

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.

NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF

The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof; wherein R1 and R2 both are hydrogen; or R1 is hydrogen and R2 is alkyl or aryl; or R1 is alkyl or aryl and R2 is hydrogen; or R1 and R2 both are alkyl or aryl (same or different groups); wherein alkyl group constitute C1-C6 alkyl or higher (both linear and branched) with or without heteroatoms; and aryl group constitute phenyl, substituted phenyl, heteraryl, arylalkyl and polynuclear aromatics. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

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).

NOVEL MURAMYL PEPTIDE DERIVATIVE COMPOUND, SYNTHESIS AND USES THEREOF

The invention relates to novel Muramyl Dipeptide (MDP) derivative compound of structural Formula-VIII, a process for synthesis, intermediates used in the synthesis and use thereof. R = alkyl (both linear and branched), aryl, substituted aryl, alkoxy alkyl Wherein, R can be both linear and branched alkyl, aryl, substituted aryl and alkoxy alkyl. These compounds possess excellent pharmacological properties, in particular immunomodulating properties for use as adjuvant in vaccine formulations. These compounds are, particularly useful as adjuvants in vaccines.

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