17041-36-0

Usage

Uses

Used in Pharmaceutical Industry:
O-(2-Acetamido-2-deoxy-D-glucopyranosyl)-L-serine is used as a key building block for the synthesis of complex carbohydrates and glycoconjugates, which play crucial roles in cellular recognition, adhesion, and signaling. These processes are essential for the development of new drugs targeting various diseases, including cancer and infectious diseases.
Used in Biomedical Research:
In the field of biomedical research, O-(2-Acetamido-2-deoxy-D-glucopyranosyl)-L-serine is utilized as a valuable tool for studying the structure and function of glycoproteins and glycolipids. Understanding the role of these biomolecules in cellular processes can lead to the discovery of novel therapeutic targets and the development of innovative diagnostic tools.
Used in Material Science:
O-(2-Acetamido-2-deoxy-D-glucopyranosyl)-L-serine can be employed in the development of biocompatible and biodegradable materials for various applications, such as drug delivery systems, tissue engineering scaffolds, and medical implants. The unique properties of O-(2-Acetamido-2-deoxy-D-glucopyranosyl)-L-serine, including its biocompatibility and ability to form stable glycosidic linkages, make it an attractive candidate for designing advanced materials with tailored properties.
Used in Food Industry:
In the food industry, O-(2-Acetamido-2-deoxy-D-glucopyranosyl)-L-serine may find applications in the development of novel food additives, preservatives, and flavor enhancers. The compound's ability to interact with other biomolecules can be exploited to improve the texture, taste, and shelf life of various food products.
Used in Cosmetics Industry:
O-(2-Acetamido-2-deoxy-D-glucopyranosyl)-L-serine can be utilized in the cosmetics industry for the development of skin care products, such as moisturizers, anti-aging creams, and sunscreens. The compound's potential to modulate cellular processes and its compatibility with biological systems make it a promising ingredient for formulating innovative cosmetic products with enhanced efficacy and safety profiles.

InChI:InChI=1/C11H20N2O8/c1-4(15)13-7-9(17)8(16)6(2-14)21-11(7)20-3-5(12)10(18)19/h5-9,11,14,16-17H,2-3,12H2,1H3,(H,13,15)(H,18,19)/t5-,6+,7+,8+,9+,11+/m0/s1

Upstream product

• 83956-40-5 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine 
• 83956-38-1 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester 
• 83956-33-6 O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-galactopyranosyl)-N-benzyloxycarbonyl-L-serine benzyl ester 
• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 
• 167688-31-5 O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine 
• 72-87-7 N-acetyl-D-galactosamine 
• 120173-57-1 N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine 
• 136497-88-6 Nα-(fluoren-9-ylmethoxycarbonyl)-3-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine allyl ester 
• 100929-03-1 benzyl O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-serinate 
• 83956-37-0 3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester 
• 83025-11-0 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl trichloroacetimidate 
• 160067-63-0 N^α-(9-flourenylmethoxycarbonyl)-3-O-(2-acetamido-2-deoxy-3,4,6-tri-O-acetyl-Β-D-glucopyranosyl)-L-serine 

Downstream Products

• 60280-57-1 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine 
• 460729-19-5 N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-[(5-acetamido-3,5-dideoxy-D-glycero-α-D-galacto-3-nonulopyranosylonic acid)-(2->6)]-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine 
• 220414-49-3 N-(benzyloxycarbonyl)-O-(3,4-O-isopropylidene-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-4,6-O-isopropylidene-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester 
• 188641-26-1 N-(benzyloxycarbonyl)-O-(β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester 
• 188641-24-9 N-(benzyloxycarbonyl)-O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-(1->3)-L-serine allyl ester 

Relevant academic research and scientific papers

Structure Guided Design of Bacteriophage Qβ Mutants as Next Generation Carriers for Conjugate Vaccines

Vaccines are critical tools to treat and prevent diseases. For an effective conjugate vaccine, the carrier is crucial, but few carriers are available for clinical applications. In addition, a drawback of current protein carriers is that high levels of antibodies against the carrier are induced by the conjugate vaccine, which are known to interfere with the immune responses against the target antigen. To overcome these challenges, we obtained the near atomic resolution crystal structure of an emerging protein carrier, i.e., the bacteriophage Qβ virus like particle. On the basis of the detailed structural information, novel mutants of bacteriophage Qβ (mQβ) have been designed, which upon conjugation with tumor associated carbohydrate antigens (TACAs), a class of important tumor antigens, elicited powerful anti-TACA IgG responses and yet produced lower levels of anticarrier antibodies as compared to those from the wild type Qβ-TACA conjugates. In a therapeutic model against an aggressive breast cancer in mice, 100% unimmunized mice succumbed to tumors in just 12 days even with chemotherapy. In contrast, 80% of mice immunized with the mQβ-TACA conjugate were completely free from tumors. Besides TACAs, to aid in the development of vaccines to protect against COVID-19, the mQβ based conjugate vaccine has been shown to induce high levels of IgG antibodies against peptide antigens from the SARS-CoV-2 virus, demonstrating its generality. Thus, mQβ is a promising next-generation carrier platform for conjugate vaccines, and structure-based rational design is a powerful strategy to develop new vaccine carriers.

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.

COMPOSITIONS AND METHODS OF TREATING CANCER AND INFECTIONS USING BACTERIOPHAGE AND ITS MUTANTS

Provided herein are vaccine composition comprising an antigen conjugated to a capsid, wherein the capsid comprises wild type or native sequence. Provided herein are also vaccine composition comprising an antigen conjugated to a capsid, wherein said capsid comprises at least one mutation, such as a non-natural mutation. Such compositions are useful in the treatment and prevention of pathogenic infections, inflammatory diseases, and neurodegenerative disease, and cancer, among others.

Utilization of bench-stable and readily available nickel(II) triflate for access to 1,2-cis-2-aminoglycosides

The utilization of substoichiometric amounts of commercially available nickel(II) triflate as an activator in the reagent-controlled glycosylation reaction for the stereoselective construction of biologically relevant targets containing 1,2-cis-2-amino gl

Stereoselective synthesis of natural and non-natural thomsen-nouveau antigens and hydrazide derivatives

A selective glycosylation strategy enabling access to all stereochemical combinations of tumor associated Thomsen-nouveau (Tn) antigen, d-GalNAc-O-Ser/Thr, has been developed. The key component for selectivity is the phthalimide-protected d- or l-amino acid acceptors which allow access to α- or β-anomers in excellent yields (72-96%) and selectivity (～100%) when appropriate C-2 substitution is installed. The glycoamino acid intermediates were divergently converted to Tn-based carboxylates or to hydrazides by tandem Pd-C debenzylation followed by treatment with hydrazine hydrate or hydrazine hydrate treatment alone.

α-Selective glycosylation affords mucin-related GalNAc amino acids and diketopiperazines active on Trypanosoma cruzi

This work addresses the synthesis and biological evaluation of glycosyl diketopiperazines (DKPs) cyclo[Asp-(αGalNAc)Ser] 3 and cyclo[Asp-(αGalNAc)Thr] 4 for the development of novel anti-trypanosomal agents and Trypanosoma cruzi trans-sialidase (TcTS) inhibitors. The target compounds were synthetized by coupling reactions between glycosyl amino acids αGalNAc-Ser 7 or αGalNAc-Thr 8 and the amino acid (O-tBu)-Asp 17, followed by one-pot deprotection-cyclisation reaction in the presence of 20% piperidine in DMF. The protected glycosyl amino acid intermediates 7 and 8 were, in turn, obtained by α-selective, HgBr2-catalysed glycosylation reactions of Fmoc-Ser/Thr benzyl esters 12/14 with αGalN3Cl 11, being, subsequently, fully deprotected for comparative biological assays. The DKPs 3 and 4 showed relevant anti-trypanosomal effects (IC50 282-124 μM), whereas glycosyl amino acids 1 and 2 showed better TcTS inhibition (57-79%) than the corresponding DKPs (13-25%).

Condensation reactions catalyzed by α-N-acetylgalactosaminidase from Aspergillus niger yielding α-N-acetylgalactosaminides

Extracellular α-N-acetylgalactosaminidase from Aspergillus niger catalyzed glycosylation yielding a series of 2-acetamido-2-deoxy-α-D- galactobiosides using 2-acetamido-2-deoxy-D-galactopyranose as a glycosyl donor. The isomers α-D-GalpNAc-(1→6)-D-GalpNAc, α-D-GalpNAc- (1→3)-D-GalpNAc and α-D-GalpNAc-(1→6)-D-GalfNAc were isolated and spectrally characterized. The purified enzyme was further used for the glycosylation of free amino acids (serine and threonine) and their N-(tert-butoxycarbonyl)-protected analogs to synthesize the Tn antigen (GalpNAc-α-O-Ser/Thr) and its N-(tert-butoxycarbonyl)-protected derivatives.

Chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant

The efficient chemoenzymatic synthesis of the Thomsen-Friedenreich antigen determinant is demonstrated under transglycosylation conditions employing β-galactosidase from bovine testes.

Azidochlorination and diazidization of glycals

The invention describes a one-pot single step procedure for the azidochlorination or diazidization of glycals, including glycal elements of carbohydrates. Compounds such as 3,4,6-tri-O-benzyl-2-azido-2-deoxy-alpha-D-galactopyranosy chloride, and 3,4,6-tri

Synthesis of the glycopeptide O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-desoxy-alpha-D-galactopyranosyl)-(1 to 3)-L-serine and -L-threonine

In the presence of silver carbonate-silver perchlorate and dichloromethane-toluene as solvent, 3,4,6-tri-O-acetyl-2-azido-2-deoxy-beta-D-galactopyranosyl chloride, and derivatives of L-serine and -L-serine and -L-threonine, gave, with high stereoselectivity, the benzyl esters of N-(benzyloxycarbonyl)-3-O-(3,4,6-tri-O-acetyl-2-azido-2-deoxy-alpha-D-galactopyranosyl)-L-serine (7) and -L-threonine (22), which were hydrogenolyzed and deblocked to give 3-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-serine and -L-threonine, respectively, corresponding to the hapten of the Tn-antigen. Reduction of the azido group of 7, followed by selective O-deacetylation and benzylidenation, gave a derivative that was glycosylated with 2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl bromide to yield a disaccharide. A similar sequence of reactions, starting from 22, gave the L-threonine analog. Removal of the protecting groups from both compounds afforded O-beta-D-galactopyranosyl-(1 to 3)-O-(2-acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-serine and -L-serine and -L-threonine, respectively, the hapten of the T-antigen.