60280-58-2

Basic information

• Product Name: T Epitope, Threonyl
• Synonyms: 3-O-b-D-galactosyl, N-acetyl-a-D-galactosaminyl-1-O-Threonine;Threonyl 2-acetamido-2-deoxy-3-O-(b-D-galactopyranosyl)-a-D-galactopyranoside;3-O-β-D-galactosyl, N-acetyl-α-D-galactosaminyl-1-O-Threonine;Threonyl 2-acetamido-2-deoxy-3-O-(b-D-galactopyranosyl)-α-D-galactopyranoside;Gal beta(1-3)GalNAc-alpha-Thr;2-Acetamido-2-deoxy-3-O-(b-D-galactopyranosyl)-a-D-galactopyranosyl threonine;O-[2-(AcetylaMino)-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl]-L-threonine;Threonyl 2-AcetaMido-2-deoxy-3-O-(β-D-galactopyranosyl)-α-D-galactopyranos ide
• CAS NO: 60280-58-2
• Molecular Formula: C18H32N2O13
• Molecular Weight: 484.452
• Product Categories: Oligosaccharide Compounds;Oligosaccharides;Amino Acids & Derivatives
• Mol File: 60280-58-2.mol
• Article Data: 5

Chemical Properties

• Melting Point: >170 (dec.)
• Boiling Point: 872.474°C at 760 mmHg
• Flash Point: 481.455°C
• Appearance: /
• Density: 1.587g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.613
• Storage Temp.: -20°C Freezer, Under Inert Atmosphere
• CAS DataBase Reference: T Epitope, Threonyl(CAS DataBase Reference)
• NIST Chemistry Reference: T Epitope, Threonyl(60280-58-2)
• EPA Substance Registry System: T Epitope, Threonyl(60280-58-2)

Safety Data

• Hazardous Substances Data: 60280-58-2(Hazardous Substances Data)

Usage

Description

T Epitope, Threonyl, also known as Galβ(1-3)GalNAc-α-Thr, is a cancer-associated carbohydrate tumor antigen that is found as a white solid. It is a promising candidate for various applications in the field of cancer research and treatment due to its unique properties and potential as a target for immunotherapy.

Uses

Used in Cancer Research and Treatment:
T Epitope, Threonyl is used as a cancer-specific target for immunotherapy. Its unique properties allow it to be recognized by the immune system, making it a potential target for the development of cancer treatments that can specifically target cancer cells without harming healthy cells.
Used in Diagnostics:
T Epitope, Threonyl is also used in the development of diagnostic monoclonal antibodies. These antibodies can be designed to specifically recognize and bind to the T Epitope, Threonyl, allowing for the detection and monitoring of cancer cells in patients.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, T Epitope, Threonyl can be used as a key component in the development of new drugs and therapies targeting cancer. Its unique properties make it a valuable tool for researchers and drug developers in their quest to create more effective and targeted cancer treatments.
Used in Biomedical Research:
T Epitope, Threonyl is also used in biomedical research as a valuable tool for studying the mechanisms of cancer cell growth and progression. Understanding the role of this antigen in cancer development can lead to the discovery of new therapeutic targets and the development of novel treatment strategies.
Overall, T Epitope, Threonyl is a versatile and promising compound with a wide range of applications in the fields of cancer research, treatment, diagnostics, and pharmaceutical development. Its unique properties and potential as a cancer-specific target make it an important focus for ongoing research and development efforts.

InChI:InChI=1/C18H32N2O13/c1-5(9(19)16(28)29)30-17-10(20-6(2)23)15(12(25)8(4-22)31-17)33-18-14(27)13(26)11(24)7(3-21)32-18/h5,7-15,17-18,21-22,24-27H,3-4,19H2,1-2H3,(H,20,23)(H,28,29)/t5-,7?,8?,9+,10+,11+,12+,13+,14+,15-,17+,18+/m1/s1

Upstream product

• 59837-14-8 p-nitrophenyl β-D-galactopyranosyl-(1->3)-2-acetamido-2-deoxy-α-D-galactopyranoside 
• 72-19-5 L-threonine 
• 83982-56-3 O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 83982-55-2 N-(Benzyloxycarbonyl)-3-O-(3,4,6-tri-O-acetyl-2-azido-2-desoxy-α-D-galactopyranosyl)-L-threoninbenzylester 
• 83956-44-9 3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 83956-46-1 3-O-(2-Acetamido-4,6-O-benzyliden-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 83956-45-0 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-threoninbenzylester 
• 67817-37-2 3,4,6-tri-O-acetyl-2-azido-2-deoxy-β-D-galactopyranosyl chloride 
• 87376-57-6 2-azido-4,6-di-O-benzoyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl bromide 
• 17041-35-9 O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-threonine 
• 3150-24-1 4-nitrophenyl-β-D-galactopyranoside 
• 96031-32-2 O-<(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1->3)-O-(2-acetamido-4,6-di-O-benzoyl-2-desoxy-α-D-galactopyranosyl)>-L-threonin 
• 83956-47-2 O-(2,3,4,6-Tetra-O-acetyl-β-D-galactopyranosyl)-(1<*>3)-O-(2-acetamido-2-desoxy-α-D-galactopyranosyl)-(1<*>3)-L-threonin 
• 96043-06-0 3-O-<2-Acetamido-4,6-di-O-benzoyl-2-desoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl>-N-benzyloxycarbonyl-L-threoninbenzylester 

Relevant articles and documents

Syntheses of mucin-type O-glycopeptides and oligosaccharides using transglycosylation and reverse-hydrolysis activities of Bifidobacterium endo-α-N-acetylgalactosaminidase

Endo-α-N-acetylgalactosaminidase catalyzes the release of Galβ1-3GalNAc from the core 1-type O-glycan (Galβ1-3GalNAcα1- Ser/Thr) of mucin glycoproteins and synthetic p-nitrophenyl (pNP) α-linked substrates. Here, we report the enzymatic syntheses of core 1 disaccharide-containing glycopeptides using the transglycosylation activity of endo-α-N-acetylgalactosaminidase (EngBF) from Bifidobacterium longum. The enzyme directly transferred Galβ1-3GalNAc to serine or threonine residues of bioactive peptides such as PAMP-12, bradykinin, peptide-T and MUC1a when Galβ1-3GalNAcα1-pNP was used as a donor substrate. The enzyme was also found to catalyze the reverse-hydrolysis reaction. EngBF synthesized the core 1 disaccharide-containing oligosaccharides when the enzyme was incubated with either glucose or lactose and Galβ1-3GalNAc prepared from porcine gastric mucin using bifidobacterial cells expressing endo-α-N- acetylgalactosaminidase. Synthesized oligosaccharides are promising prebiotics for bifidobacteria.

BLOCKSYNTHESE VON O-GLYCOPEPTIDEN UND ANDEREN T-ANTIGEN STRUKTUREN

Under the conditions of in situ anomerisation, the 2-azido-4,6-di-O-benzoyl-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl bromide reacted directly and with high selectivity with the reactive hydroxyl groups of L-serine and L-threonine derivatives to form α-glycosidically-linked products.Thus, the glycopeptides containing L-serine and L-threonine are more accessible.The disaccharide block could also be coupled with other reactive hydroxyl compounds to give compounds that contain the T-receptor.

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.