4539-83-7

Upstream product

• 108-24-7 acetic anhydride 
• 113532-33-5 2-amino-2-deoxy-D-idose; hydrochloride 
• 5432-46-2 1,3,4,6-tetra-O-acetyl-D-glucosamine hydrochloride 
• 66-84-2 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 
• 81336-82-5 2-(trimethylsilyl)ethyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 64-19-7 acetic acid 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 3006-60-8 Acetic acid (2R,3R,4R,5S,6R)-2,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-4-yl ester 
• 10036-64-3 N-acetyl-D-glucosamine 
• 7512-17-6 2-acetamido-2-deoxy-D-glucose 
• 75-36-5 acetyl chloride 
• 10387-40-3 potassium thioacetate 

Downstream Products

• 13089-27-5 p-nitrophenyl 2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranoside 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 
• 10378-06-0 2-methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyranoso)[1,2-d]-2-oxazoline 
• 2771-48-4 methyl 2-acetamido-3,4,6-O-triacetyl-2-deoxy-β-D-glucopyranoside 
• 72333-20-1 allyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-(1->4)-2,4,6-tri-O-benzyl-α-D-galactopyranoside 
• 160168-40-1 N^α-fluoren-9-ylmethoxycarbonyl-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-β-D-glucopyranosyl)-L-threonine 
• 160067-63-0 N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine 
• 27526-42-7 phenyl 2-acetamido-3,4,6-tri-O-acetyl-1,2-di-deoxy-1-thio-β-D-glucopyranoside 
• 72333-19-8 propyl 2-acetamido-3-O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-4,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 84218-49-5 O-(N-acetamido-2-tri-O-acetyl-3,4,6-desoxy-2-β-D-glucopyranosyl)-4-O-acetyl-1-tri-O-benzyl-2,3,5-D-ribitol 
• 4239-72-9 ethyl 2-acetamido-3,4,6-tetra-O-acetyl-2-deoxy-1-thio-β-D-glucopyranoside 
• 6205-69-2 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl azide 
• 10294-12-9 2-deoxy-2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranose 
• 70749-28-9 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-β-D-glucopyranose 

Relevant academic research and scientific papers

Simple and efficient per-O-acetylation of carbohydrates by lithium perchlorate catalyst

Lithium perchlorate is demonstrated to be a highly efficient and convenient catalyst for the per-O-acetylation of various saccharides with excellent yields. Graphical Abstract

Synthesis and biological evaluation of 3β-O-neoglycosides of caudatin and its analogues as potential anticancer agents

In order to study the structure–activity relationship (SAR) of C21-steroidal glycosides toward human cancer cell lines and explore more potential anticancer agents, a series of 3β-O-neoglycosides of caudatin and its analogues were synthesized. The results revealed that most of peracetylated 3β-O-monoglycosides demonstrated moderate to significant antiproliferative activities against four human cancer cell lines (MCF-7, HCT-116, HeLa, and HepG2). Among them, 3β-O-(2,3,4-tri-O-acetyl-β-L-glucopyranosyl)-caudatin (2k) exhibited the highest antiproliferative activity aganist HepG2 cells with an IC50 value of 3.11 μM. Mechanical studies showed that compound 2k induced both apoptosis and cell cycle arrest at S phase in a dose dependent manner. Overall, these present findings suggested that glycosylation is a promising scaffold to improve anticancer activity for naturally occurring C21-steroidal aglycones, and compound 2k represents a potential anticancer agent deserved further investigation.

S-ANTIGEN TRANSPORT INHIBITING OLIGONUCLEOTIDE POLYMERS AND METHODS

Various embodiments provide STOPS? polymers that are S-antigen transport inhibiting oligonucleotide polymers, processes for making them and methods of using them to treat diseases and conditions. In some embodiments the STOPS? modified oligonucleotides include an at least partially phosphorothioated sequence of alternating A and C units having modifications as described herein. The sequence independent antiviral activity against hepatitis B of embodiments of STOPS? modified oligonucleotides, as determined by HBsAg Secretion Assay, is an EC50 that is less than 100 nM.

A silyl ether-protected building block forO-GlcNAcylated peptide synthesis to enable one-pot acidic deprotection

In this report, we introduce a novel building block for Fmoc/tBu solid phase peptide synthesis (SPPS) of β-linkedO-GlcNAcylated peptides. This building block carries acid labile silyl ether protecting groups, which are fully removed under TFA-mediated peptide cleavage conditions from the resin, thus requiring fewer synthetic steps and no intermediate purification as compared to other acid or base labile protecting group strategies.

2,3-Carbamate mannosamine glycosyl donors in glycosylation reactions of diacetone-D-glucose. An experimental and theoretical study

The role of the cyclic 2,3-N,O-carbamate protecting group in directing the selectivity of mannosylation reactions of diacetone-D-glucose, promoted by BSP/Tf2O via α-triflate intermediates, has been investigated through a combined computational

Synthesis of Asparagine Derivatives Harboring a Lewis X Type DC-SIGN Ligand and Evaluation of their Impact on Immunomodulation in Multiple Sclerosis

The protein myelin oligodendrocyte glycoprotein (MOG) is a key component of myelin and an autoantigen in the disease multiple sclerosis (MS). Post-translational N-glycosylation of Asn31 of MOG seems to play a key role in modulating the immune response towards myelin. This is mediated by the interaction of Lewis-type glycan structures in the N-glycan of MOG with the DC-SIGN receptor on dendritic cells (DCs). Here, we report the synthesis of an unnatural Lewis X (LeX)-containing Fmoc-SPPS-compatible asparagine building block (SPPS=solid-phase peptide synthesis), as well as asparagine building blocks containing two LeX-derived oligosaccharides: LacNAc and Fucα1-3GlcNAc. These building blocks were used for the glycosylation of the immunodominant portion of MOG (MOG31-55) and analyzed with respect to their ability to bind to DC-SIGN in different biological setups, as well as their ability to inhibit the citrullination-induced aggregation of MOG31-55. Finally, a cytokine secretion assay was carried out on human monocyte-derived DCs, which showed the ability of the neoglycopeptide decorated with a single LeX to alter the balance of pro- and anti-inflammatory cytokines, inducing a tolerogenic response.

Substituted pyrazole compound, preparation method, pharmaceutical composition and applications thereof

The invention discloses a substituted pyrazole compound represented by a formula I, and a preparation method, a pharmaceutical composition and applications thereof, wherein the compound has characteristics of good stability, excellent solubility, low cytotoxicity and remarkable neuroprotective effect, can effectively prevent and treat nerve cell injury, and is an ideal medicinal compound for preventing or treating cerebral stroke, cerebral embolism, cerebral stroke sequelae, cerebral stroke dyskinesia, mitochondrial encephalomyopathy and amyotrophic lateral sclerosis of spinal cord.

Protein S-Glyco-Modification through an Elimination-Addition Mechanism

Per-O-acetylated unnatural monosaccharides containing a bioorthogonal group have been widely used for metabolic glycan labeling (MGL) in live cells for two decades, but it is only recently that we discovered the existence of an artificial "S-glycosylation" between protein cysteines and per-O-acetylated sugars. While efforts are being made to avoid this nonspecific reaction in MGL, the reaction mechanism remains unknown. Here, we present a detailed mechanistic investigation, which unveils the "S-glycosylation" being an atypical glycosylation termed S-glyco-modification. In alkaline protein microenvironments, per-O-acetylated monosaccharides undergo base-promoted β-elimination to form thiol-reactive α,β-unsaturated aldehydes, which then react with cysteine residues via Michael addition. This S-glyco-modification produces 3-thiolated sugars in hemiacetal form, rather than typical glycosides. The elimination-addition mechanism guides us to develop 1,6-di-O-propionyl-N-azidoacetylgalactosamine (1,6-Pr2GalNAz) as an improved unnatural monosaccharide for MGL.

A terpyridine zinc complex for selective detection of lipid pyrophosphates: A model system for monitoring bacterial O- And N-transglycosylations

To develop an effective method for probing O- and Nglycosyltransfer reactions that are accompanied by the release of undecaprenyl pyrophosphate, solanesyl pyrophosphate (SPP) is used as a surrogate to bind a terpyridine zinc complex (Tpy-Zn), forming a fluorescent [Tpy-Zn]-SPP complex (Kass 106,000 M-1 in EtOH-CHCl3) with 5.8 μM LOD in HEPES buffer (10 mM, pH 7.4) containing 10 mM CaCl2 and 0.08% decyl PEG, which is similar to the bioassay conditions for lipid II polymerization.

Pseudo-enantiomeric carbohydrate-based N-heterocyclic carbenes as promising chiral ligands for enantiotopic discrimination

The practical synthesis of carbohydrate-based NHC-Rh complexes bearing C1 or C3 sterically differentiated positions, accessed by glycosylation or SNAr strategies, is reported. These catalysts exhibit pseudo-enantiomeric behaviour in the hydrosilylation of acetophenone. We show that steric bulk at C1 gives preference for (S)-phenyl-1-ethanol, while bulk at C3 leads to the (R)-enantiomer. These results represent the first example of pseudo-enantiomeric carbohydrate-based NHC ligands leading to enantiotopic discrimination.