(2S)-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}propanoic acid

• ChemBase ID: 169337
• Molecular Formular: C32H36N2O13
• Molecular Mass: 656.63384
• Monoisotopic Mass: 656.22173922
• SMILES: c1ccc2c(c1)C(c1c2cccc1)COC(=O)N[C@@H](CO[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(=O)O
• Canonical SMILES: CC(=O)OC[C@@H]1O[C@H](OC[C@@H](C(=O)O)NC(=O)OCC2c3ccccc3c3c2cccc3)[C@H]([C@H]([C@H]1OC(=O)C)OC(=O)C)NC(=O)C
• InChI: InChI=1S/C32H36N2O13/c1-16(35)33-27-29(46-19(4)38)28(45-18(3)37)26(15-42-17(2)36)47-31(27)43-14-25(30(39)40)34-32(41)44-13-24-22-11-7-5-9-20(22)21-10-6-8-12-23(21)24/h5-12,24-29,31H,13-15H2,1-4H3,(H,33,35)(H,34,41)(H,39,40)/t25-,26+,27+,28-,29+,31-/m0/s1
• InChIKey: ORICVOOXZDVFIP-VOZJJELXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-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}propanoic acid
• IUPAC Traditional name: (2S)-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}propanoic acid
• Synonyms: N-[(9H-Fluoren-9-ylmethoxy)carbonyl]-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranosyl]-L-serine; Fmoc-Ser(2-acetamido-3,4,6,-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-OH; Fmoc-Ser-(Ac3AcNH-α-Gal)-OH; N-Fmoc-O-[3,4,6-tri-O-acetyl-2-(acetylamino)-2-deoxy-α-D-galactopyranosyl]-L-serine

Database IDs

• CAS Number: 120173-57-1
• PubChem SID: 162263469
• PubChem CID: 10908465

CALCULATED PROPERTIES

• Acid pKa: 3.3809648
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -0.84287906
• LogD (pH = 7.4): -2.1447508
• Log P: 1.2629125
• Molar Refractivity: 157.0899 cm^3
• Polarizability: 64.13853 Å^3
• Polar Surface Area: 202.09 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F667900

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)