67262-86-6

Basic information

• Product Name: TN ANTIGEN
• Synonyms: GALNAC-ALPHA1-O-SER;SERINYL 2-ACETAMIDO-2-DEOXY-A-GALACTOPYRANOSIDE;N-ACETYLGALACTOSAMINE, ALPHA1-O-SERINE;N-ACETYL-ALPHA-D-GALACTOSAMINYL-1-O-SERINE;TN EPITOPE;TN ANTIGEN;Serinyl 2-acetamido-2-deoxy-a-galactopyranoside, N-acetyl-a-D-galactosaminyl-1-O-serine;Serinyl 2-acetamido-2-deoxy-α-galactopyranoside, N-acetyl-α-D-galactosaminyl-1-O-serine
• CAS NO: 67262-86-6
• Molecular Formula: C₁₁H₂₀N₂O₈
• Molecular Weight: 308.29
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives;Amino Acids & Derivatives
• Mol File: 67262-86-6.mol
• Article Data: 9

Chemical Properties

• Melting Point: 198-201°C
• Boiling Point: 701.205°C at 760 mmHg
• Flash Point: 377.875°C
• Appearance: /
• Density: 1.517g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.583
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Water
• PKA: 2.05±0.10(Predicted)
• Stability: HYGROSCOPIC
• CAS DataBase Reference: TN ANTIGEN(CAS DataBase Reference)
• NIST Chemistry Reference: TN ANTIGEN(67262-86-6)
• EPA Substance Registry System: TN ANTIGEN(67262-86-6)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 67262-86-6(Hazardous Substances Data)

Usage

Description

TN ANTIGEN, also known as Thomsen-Friedenreich Antigen, is a cancer-associated carbohydrate tumor antigen that plays a significant role in the field of cancer research and treatment. It is characterized by its unique structure and properties, which make it a promising target for immunotherapy and diagnostic applications.
Source:
TN ANTIGEN is primarily found in various types of cancer cells, where it is overexpressed compared to normal cells. It is also present in some normal tissues, but at much lower levels.
Production Methods:
The production of TN ANTIGEN involves the enzymatic modification of glycoproteins and glycolipids, which leads to the exposure of the antigenic structure. This process can be achieved through various biochemical and biotechnological approaches.

Uses

Used in Cancer Immunotherapy:
TN ANTIGEN is used as a cancer-specific target for immunotherapy, as it is overexpressed in various types of cancer cells. It has the potential to stimulate the immune system to recognize and attack cancer cells, leading to the destruction of tumors and prevention of metastasis.
Used in Diagnostic Monoclonal Antibodies:
TN ANTIGEN is used in the development of diagnostic monoclonal antibodies, which can specifically bind to the antigen and help in the detection and monitoring of cancer. These antibodies can be used in various diagnostic assays, such as immunohistochemistry, flow cytometry, and enzyme-linked immunosorbent assays (ELISA).
Used in Human Vaccines:
TN ANTIGEN has been used or considered for use in human vaccines, as it can potentially elicit an immune response against cancer cells. Vaccines targeting TN ANTIGEN may help in the prevention of cancer development or the recurrence of the disease in patients who have already been treated.

Biochem/physiol Actions

Tn antigen stimulates colorectal cancer metastasis through the activation of epithelial-mesenchymal transition, mediated by H-Ras. It acts as a precursor to several significant complex O-glycans. Subpopulations of blood cells in all lineages carrying the Tn antigen results in a hematological disorder called Tn syndrome.

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

• 83956-33-6 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 
• 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 
• 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 
• 120173-57-1 N-(9-fluorenylmethoxycarbonyl)-O-(3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α-D-galactopyranosyl)-L-serine 
• 72-87-7 N-acetyl-D-galactosamine 
• 167688-31-5 O-(2-acetamido-2-deoxy-α-D-galactopyranosyl)-N-(tert-butoxycarbonyl)-L-serine 
• 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 
• 83956-38-1 3-O-(2-Acetamido-2-desoxy-α-D-galactopyranosyl)-N-(benzyloxycarbonyl)-L-serinbenzylester 
• 83956-40-5 O-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-L-serine 

Downstream Products

• 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 
• 60280-57-1 3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine 

Relevant articles and documents

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.

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

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%).