(2S,3R)-3-{[(2S,3R,4R,5R,6R)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]-3-acetamidooxan-2-yl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid

• ChemBase ID: 169338
• Molecular Formular: C33H38N2O13
• Molecular Mass: 670.66042
• Monoisotopic Mass: 670.23738929
• SMILES: c1ccc2c(c1)C(c1c2cccc1)COC(=O)N[C@@H]([C@H](O[C@@H]1[C@H]([C@H]([C@H]([C@@H](O1)COC(=O)C)OC(=O)C)OC(=O)C)NC(=O)C)C)C(=O)O
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@H](O[C@@H]([C@@H](C(=O)O)NC(=O)OCC2c3ccccc3c3c2cccc3)C)[C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C33H38N2O13/c1-16(27(31(40)41)35-33(42)44-14-25-23-12-8-6-10-21(23)22-11-7-9-13-24(22)25)45-32-28(34-17(2)36)30(47-20(5)39)29(46-19(4)38)26(48-32)15-43-18(3)37/h6-13,16,25-30,32H,14-15H2,1-5H3,(H,34,36)(H,35,42)(H,40,41)/t16-,26-,27+,28-,29+,30-,32+/m1/s1
• InChIKey: OXLCJWGAUPPZQJ-ZNHCDWFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3R)-3-{[(2S,3R,4R,5R,6R)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]-3-acetamidooxan-2-yl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid
• IUPAC Traditional name: (2S,3R)-3-{[(2S,3R,4R,5R,6R)-4,5-bis(acetyloxy)-6-[(acetyloxy)methyl]-3-acetamidooxan-2-yl]oxy}-2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}butanoic acid
• Synonyms: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranosyl]-L-threonine; Fmoc-Thr(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-OH; Fmoc-Thr-(Ac3AcNH-α-Gal)-OH; N-Fmoc-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranosyl]-L-threonine

Database IDs

• CAS Number: 116783-35-8
• PubChem SID: 162263470
• PubChem CID: 11050650

CALCULATED PROPERTIES

• Acid pKa: 3.416131
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -0.3926776
• LogD (pH = 7.4): -1.7193078
• Log P: 1.6794876
• Molar Refractivity: 161.5087 cm^3
• Polarizability: 65.96606 Å^3
• Polar Surface Area: 202.09 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F667920

Fluorescently labeled glycopeptides containing GalNAcα1-O-Ser/Thr residues provide valuable immunology probes for the development of cancer vaccines.

REFERENCES

• Hanisch, F., et al.: Biol. Chem., 382, 143 (2001)
• Davis, B., et al.: Science, 303, 480 (2001)
• Hang, H., et al.: Bioorg. Med. Chem., 13, 5021 (2001)