67262-86-6 , TN ANTIGEN, GalNac-α-1-O-serine, CAS:67262-86-6
C11H20N2O8 / 308.29
MFCD01863462
2-Acetamido-2-deoxy-a-D-galactopyranosyl serine
2-Acetamido-2-deoxy-a-D-galactopyranosyl serine (2AGPS) is a naturally occurring glycosaminoglycan. It has been shown to inhibit the growth of cancer cells and to reduce the size of mouse tumors in vivo. This compound also inhibits viral replication in vitro, and its antiviral properties have been shown to work on several different types of viruses, including herpes simplex virus type 1, human cytomegalovirus, and influenza A virus. 2AGPS is also a potent inducer of toll-like receptor 4 signaling pathways in macrophages and dendritic cells. 2AGPS can be synthesized by using a polymerase chain reaction (PCR) technique with synthetic oligosaccharides as a template.
O-(2-Acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-serine or GalNAc-Ser (GalNAc = N-Acetyl-D-galactosamine) is a glycosylation product found in diverse biological systems, including mucus, serum glycoproteins, and extracellular matrix proteins. It is a highly conserved feature of the glycoproteins that play a vital role in various biological processes such as signal transduction, cell adhesion, and antigen recognition. In this paper, we will explore the various aspects of GalNAc-Ser, including its physical and chemical properties, synthesis, characterization, analytical methods, biological properties, toxicity, safety, applications, current state of research, potential implications, limitations, and future directions.
Definition and Background:
GalNAc-Ser is a type of carbohydrate moiety that is covalently linked to the hydroxyl group of serine on the protein or peptide backbone. This process is referred to as O-glycosylation, which is a type of post-translational modification. The glycosylation of proteins is an essential process that adds diversity and complexity to the proteome, which results in the regulation of various biological functions.
Synthesis and Characterization:
GalNAc-Ser is synthesized through the action of specific enzymes, which recognize and modify the hydroxyl group of serine residues on the protein or peptide backbone. The modification is usually initiated by the transfer of N-acetylgalactosamine (GalNAc) to the hydroxyl group of serine, resulting in GalNAc-Ser. The specific glycosyltransferases involved in the synthesis of GalNAc-Ser depend on the cell type, tissue, and developmental stage.
Analytical Methods:
The most commonly used analytical methods for the detection and quantification of GalNAc-Ser in biological samples are mass spectrometry, liquid chromatography, and lectin-based assays. These methods are highly sensitive and specific, enabling the detection of even trace amounts of the molecule in complex biological samples.
Biological Properties:
GalNAc-Ser is a highly conserved glycosylation product that plays a vital role in modulating various biological processes. Its biological activity is dependent on its stereochemistry, which affects its interaction with other biological molecules such as lectins and antibodies. The carbohydrate moiety is known to affect the immunogenicity of proteins, enabling the modulation of immune responses.
Toxicity and Safety in Scientific Experiments:
GalNAc-Ser is generally considered safe and non-toxic, as it is a natural product found in various biological systems. However, as with any chemical substance, the toxicity of GalNAc-Ser depends on its concentration, route of administration, and exposure duration. Therefore, caution should be taken when working with GalNAc-Ser to avoid exposure or accidental ingestion.
Applications in Scientific Experiments:
GalNAc-Ser has significant applications in various scientific experiments, including protein glycosylation studies, biomarker discovery, immunogenicity studies, and drug delivery. Its unique stereochemistry and biological activity enable the modulation of various biological processes, making it an attractive target for therapeutic interventions.
Current State of Research:
The current state of research on GalNAc-Ser is focused on elucidating its role in various biological processes, including signal transduction, cell adhesion, and antigen recognition. The recent advancements in analytical techniques have enabled the detection of GalNAc-Ser in complex biological samples, enabling the investigation of its biological function and activity.
Potential Implications in Various Fields of Research and Industry:
The potential implications of GalNAc-Ser in various fields of research and industry are significant, including the development of new drugs, vaccines, and biomarkers. The ability to modulate immune responses through the manipulation of GalNAc-Ser has significant implications for the treatment of various autoimmune diseases and cancer.
Limitations and Future Directions:
Despite the significant potential for GalNAc-Ser, several limitations need to be addressed, including the development of better analytical techniques for its detection, the identification of specific glycosyltransferases involved in its synthesis and regulation, and the standardization of protocols for its safe handling. Furthermore, future directions should focus on the investigation of the structure-activity relationship of GalNAc-Ser and the development of new therapeutic interventions based on its biological activity.
Future Directions:
- Investigation of the role of GalNAc-Ser in modulating immune responses in autoimmune diseases and cancer.
- Development of new analytical techniques for the detection and quantification of GalNAc-Ser in complex biological samples.
- Identification of specific glycosyltransferases involved in the synthesis and regulation of GalNAc-Ser.
- Investigation of the structure-activity relationship of GalNAc-Ser to develop new therapeutic interventions.
- Standardization of protocols for the safe handling of GalNAc-Ser in scientific experiments and industry.
- Exploration of the potential of GalNAc-Ser as a biomarker for the diagnosis and prognosis of various diseases.
- Investigation of the effect of GalNAc-Ser-containing proteins on the immune system.
- Integration of GalNAc-Ser into drug delivery systems to enhance their efficacy and specificity.
- Development of GalNAc-Ser-based immunotherapies for the treatment of autoimmune diseases and cancer.
CAS Number | 67262-86-6 |
Product Name | O-(2-Acetamido-2-deoxy-alpha-D-galactopyranosyl)-L-serine |
IUPAC Name | (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-aminopropanoic acid |
Molecular Formula | C11H20N2O8 |
Molecular Weight | 308.29 g/mol |
InChI | InChI=1S/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 |
InChI Key | REDMNGDGDYFZRE-WKWISIMFSA-N |
SMILES | CC(=O)NC1C(C(C(OC1OCC(C(=O)O)N)CO)O)O |
Synonyms | Serinyl 2-Acetamido-2-deoxy-α-galactopyranoside; N-Acetyl-α-D-galactosaminyl-1-O-serine; O-[2-(Acetylamino)-2-deoxy-α-D-galactopyranosyl]-L-serine; |
Canonical SMILES | CC(=O)NC1C(C(C(OC1OCC(C(=O)O)N)CO)O)O |
Isomeric SMILES | CC(=O)N[C@@H]1[C@H]([C@H]([C@H](O[C@@H]1OC[C@@H](C(=O)O)N)CO)O)O |
CAS No: 67262-86-6 Synonyms: N-Acetyl-a-D-galactosaminyl-1-O-serineTn AntigenGalNAc-a-1-O-Serine MDL No: MFCD01863462 Chemical Formula: C11H20N2O8 Molecular Weight: 308.29 |
Contact: Miss.Xing
Phone: 18310328607 , 13621067991,13552979007
Tel: 86+10-61274189
Email: chemsynlab@163.com, zhangchao@chemsynlab.com
Add: A411 Room,No.26,Jinyuan Road,Daxing Industrial Developing District,Beijing,China post code:102628