(2R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6S)-6-[(2S)-2-carboxy-2-acetamidoethoxy]-5-acetamido-3,4-dihydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

• ChemBase ID: 177884
• Molecular Formular: C24H39N3O17
• Molecular Mass: 641.57636
• Monoisotopic Mass: 641.2279468
• SMILES: [C@H]1([C@@H]([C@@H]([C@H](O[C@H]1CO[C@@]1(C[C@H]([C@H]([C@@H](O1)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)OC[C@H](NC(=O)C)C(=O)O)NC(=O)C)O)O
• Canonical SMILES: OC[C@H]([C@H]([C@@H]1O[C@](OC[C@@H]2O[C@H](OC[C@@H](C(=O)O)NC(=O)C)[C@H]([C@H]([C@H]2O)O)NC(=O)C)(C[C@H]([C@H]1NC(=O)C)O)C(=O)O)O)O
• InChI: InChI=1S/C24H39N3O17/c1-8(29)25-11(21(37)38)6-41-22-16(27-10(3)31)19(36)18(35)14(43-22)7-42-24(23(39)40)4-12(32)15(26-9(2)30)20(44-24)17(34)13(33)5-28/h11-20,22,28,32-36H,4-7H2,1-3H3,(H,25,29)(H,26,30)(H,27,31)(H,37,38)(H,39,40)/t11-,12-,13+,14+,15+,16+,17+,18-,19+,20+,22-,24+/m0/s1
• InChIKey: XTQCCEVOMHPMKD-ZUQXEXIASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6S)-6-[(2S)-2-carboxy-2-acetamidoethoxy]-5-acetamido-3,4-dihydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• IUPAC Traditional name: (2R,4S,5R,6R)-2-{[(2R,3R,4R,5R,6S)-6-[(2S)-2-carboxy-2-acetamidoethoxy]-5-acetamido-3,4-dihydroxyoxan-2-yl]methoxy}-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
• Synonyms: 6-O-α-Sialyl-2-acetamido-2-deoxy-α-D-galactopyranosyl-1-O-L-serine N-Acetate; N-Acetyl-O-[2-(acetylamino)-6-O-(N-acetyl-α-neuraminosyl)-2-deoxy-α-D-galactopyranosyl]-L-serine; STn Epitope N-Acetate

Database IDs

• CAS Number: 385398-89-0
• PubChem SID: 164233794
• PubChem CID: 71752246

CALCULATED PROPERTIES

• Acid pKa: 2.8517747
• H Acceptors: 17
• H Donor: 11
• LogD (pH = 5.5): -10.795512
• LogD (pH = 7.4): -13.136697
• Log P: -6.2678795
• Molar Refractivity: 135.2707 cm^3
• Polarizability: 55.480515 Å^3
• Polar Surface Area: 320.2 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Warm Methanol; Water
• Apperance: Off-White Amorphous Solid

Safety Information

• Storage Warning: Moisture Sensitive

DETAILS

Toronto Research Chemicals - S687050

Sialosyl-Tn epitope is a cancer associated carbohydrate antigen which may be effective as cancer specific targets for immunotherapy as well as in the development of diagnostic monoclonal antibodies. These antigens appear as clusters of glycopeptide repea

REFERENCES

• Kim, J.M., and Roy, R.: Tetrahedron Lett., 38, 3487 (1997)
• Qiu, D., and Koganty, R.: Tetrahedron Lett., 38, 961 (1997)
• Toyokuni, T., and Singhal, A.K.: Chem. Soc. Rev., 231, (1995)