O-(N-acetyl-alpha-D-galactosaminyl)-L-serine
Basic information
- CAS
67262-86-6- Standard SMILES
CC(=O)N[C@H]1[C@@H](OC[C@H](N)C(=O)O)O[C@H](CO)[C@H](O)[C@@H]1O- InChIKey
REDMNGDGDYFZRE-WKWISIMFSA-N- Molecular formula
- C11H20N2O8
- Average molar mass
- 308.29 g/mol
- Monoisotopic mass
- 308.1219656
Overview
O-(N-acetyl-alpha-D-galactosaminyl)-L-serine is a non-proteinogenic L-amino acid that is N-acetyl-alpha-D-galactosamine linked via an alpha glycosidic bond to the O at position 3 of L-serine. It has a role as a tumour antigen. It is a non-proteinogenic L-alpha-amino acid and a L-serine derivative.
Names & identifiers
- Preferred name
- O-(N-acetyl-alpha-D-galactosaminyl)-L-serine
- IUPAC
- (2S)-3-[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-aminopropanoic acid
- English name
- TN ANTIGEN
- Molecular formula
- C11H20N2O8
- Molecular weight
- 308.29
Names & synonyms
Tn Antigen67262-86-6alpha-D-GalNAc-SerO-(2-ACETAMIDO-2-DEOXY-ALPHA-D-GALACTOPYRANOSYL)-L-SERINEO-(N-acetyl-alpha-D-galactosaminyl)-L-serineGalNAc(alpha1->O)SerCHEBI:53608O-[2-(Acetylamino)-2-deoxy-alpha-D-galactopyranosyl]-L-serineO-(2-(acetylamino)-2-deoxy-alpha-D-galactopyranosyl)-L-serineGalNAc-1-serineGalNAcalpha1-ThrGalNAc-1-threonine
Show more names
TN EPITOPESer(α-D-GalNHAc)-OHGALNAC-ALPHA1-O-SERGalNac-α-1-O-serineOlanzapine Impurity 50Tn Antigen: H-Ser(α-D-GalNAc)-OHGalactose Impurity 9 (Tn Epitope)N-ACETYLGALACTOSAMINE, ALPHA1-O-SERINEN-Acetyl-α-D-galactosaMinyl- 1-O-serine
Thomsen-Nouveau antigenThomsen-nouvelle antigenalpha-D-GalpNAc-ONH2CD175 protein, humanN-Acetyl-alpha-D-galactosaminyl-1-O-serineRefChem:167107GalNac-alpha-1-O-serineCD175
Properties
Computed structural properties
- XLogP
- -5.6
- Topological polar surface area
- 172 Ų
- Hydrogen bond donors
- 6
- Hydrogen bond acceptors
- 9
- Rotatable bonds
- 6
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 379
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Melting point
- 198 · 198-201°C
- Boiling point
- 701.2 · 701.2±60.0 °C(Predicted)
- Density
- 1.51 · 1.51±0.1 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Water
- pka
- 2.05 · 2.05±0.10(Predicted)
- form
- Solid
- color
- Off-White to Yellow
- Stability
- HYGROSCOPIC
- 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
- InChIKey
- REDMNGDGDYFZRE-WKWISIMFSA-N
- SMILES
- CC(=O)N[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1OC[C@H](N)C(O)=O
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesA cancer associated carbohydrate tumor antigen which may be effective as cancer specific targets for immunotherapy as well as in the development of diagnostic monoclonal antibodies. Has been used or considered for use in human vaccines.
UsesTN ANTIGEN is a cancer associated carbohydrate tumor antigen which may be effective as cancer specific targets for immunotherapy as well as in the development of diagnostic monoclonal antibodies. Has been used or considered for use in human vaccines
General DescriptionTn antigenis a truncated O-glycan, that is commonly noticed in colorectal cancer (CRC). It is usually expressed at high levels in cancer cells. Tn antigen is small in size and simple in structure. It has a non-physiological glycan structure in humans, hence it may be identified as foreign by the immune system.
Additional notes
DefinitionChEBI: O-(N-acetyl-alpha-D-galactosaminyl)-L-serine is a non-proteinogenic L-amino acid that is N-acetyl-alpha-D-galactosamine linked via an alpha glycosidic bond to the O at position 3 of L-serine. It has a role as a tumour antigen. It is a L-serine derivative and a non-proteinogenic L-alpha-amino acid.
Related reactions
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Compound notes
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