(2S)-2-amino-3-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid

• ChemBase ID: 154526
• Molecular Formular: C11H20N2O8
• Molecular Mass: 308.2851
• Monoisotopic Mass: 308.12196561
• 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
• Canonical SMILES: OC[C@H]1O[C@H](OC[C@@H](C(=O)O)N)[C@@H]([C@H]([C@H]1O)O)NC(=O)C
• 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
• InChIKey: REDMNGDGDYFZRE-WKWISIMFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3-{[(2S,3R,4R,5R,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propanoic acid
• IUPAC Traditional name: GalNAcα1-Ser
• Synonyms: GalNac-α-1-O-serine; O-[2-(Acetylamino)-2-deoxy-α-D-galactopyranosyl]-L-serine; Tn Antigen; Serinyl 2-Acetamido-2-deoxy-α-galactopyranoside; N-Acetyl-α-D-galactosaminyl-1-O-serine; Tn Epitope

Database IDs

• CAS Number: 67262-86-6
• MDL Number: MFCD01863462
• PubChem SID: 162248665
• PubChem CID: 447272

CALCULATED PROPERTIES

• Acid pKa: 1.8044195
• H Acceptors: 9
• H Donor: 6
• LogD (pH = 5.5): -5.9466543
• LogD (pH = 7.4): -5.961738
• Log P: -5.946677
• Molar Refractivity: 65.5556 cm^3
• Polarizability: 27.125751 Å^3
• Polar Surface Area: 171.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Water
• Apperance: Off-White to Yellow Solid
• Melting Point: 182-188°C (dec.)

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Storage Warning: HYGROSCOPIC
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥99.0% (TLC)
• Empirical Formula (Hill Notation): C11H20N2O8

DETAILS

Toronto Research Chemicals - T020050

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.

REFERENCES

• Springer, G., et al.: Science, 224, 1198 (1984)
• Springer, G., et al.: J. Mol. Med., 75, 594 (1984)
• Iida, S., et al.: J. Biol. Chem., 274, 10697 (1984)
• Wu, A., et al.: Biochem. J., 371, 311 (1984)