5-(2-{[(tert-butoxy)carbonyl]amino}-3-(methanesulfonylsulfanyl)propanamido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid

• ChemBase ID: 162510
• Molecular Formular: C29H28N2O10S2
• Molecular Mass: 628.67002
• Monoisotopic Mass: 628.11853711
• SMILES: c12c(cc(cc1)O)oc1c(c2c2ccc(cc2C(=O)O)NC(=O)C(CSS(=O)(=O)C)NC(=O)OC(C)(C)C)ccc(=O)c1
• Canonical SMILES: O=C(OC(C)(C)C)NC(C(=O)Nc1ccc(c(c1)C(=O)O)c1c2ccc(=O)cc2oc2c1ccc(c2)O)CSS(=O)(=O)C
• InChI: InChI=1S/C29H28N2O10S2/c1-29(2,3)41-28(37)31-22(14-42-43(4,38)39)26(34)30-15-5-8-18(21(11-15)27(35)36)25-19-9-6-16(32)12-23(19)40-24-13-17(33)7-10-20(24)25/h5-13,22,32H,14H2,1-4H3,(H,30,34)(H,31,37)(H,35,36)
• InChIKey: ZZUGASBFWLQFLK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-(2-{[(tert-butoxy)carbonyl]amino}-3-(methanesulfonylsulfanyl)propanamido)-2-(6-hydroxy-3-oxo-3H-xanthen-9-yl)benzoic acid
• IUPAC Traditional name: 5-{2-[(tert-butoxycarbonyl)amino]-3-(methanesulfonylsulfanyl)propanamido}-2-(3-hydroxy-6-oxoxanthen-9-yl)benzoic acid
• Synonyms: t-Boc-MTSEA-Fluorescein; (L)-2-[(t-Boc)amino]-2-[(5-Fluoresceinyl)aminocarbonyl]ethyl Methanethiosulfonate

Database IDs

• CAS Number: 1042688-20-9
• PubChem SID: 162256645
• PubChem CID: 5175853

CALCULATED PROPERTIES

• LogD (pH = 5.5): 0.46173203
• LogD (pH = 7.4): -1.8214264
• Log P: 2.1430387
• Molar Refractivity: 171.9077 cm^3
• Polarizability: 61.49704 Å^3
• Polar Surface Area: 185.4 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 2.8207345
• H Acceptors: 9
• H Donor: 4

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Methanol
• Apperance: Yellow to Orange Solid

Safety Information

• Storage Condition: Amber Vial, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B619050

A thiol specific fluorescent probe useful for ion channel and protein topology research. The recently available MTS-fluorophores may find application in the real-time monitoring of conformational changes, since fluorophores coupled to introduced cysteine

REFERENCES

• Mannuzzu, L.M., et al.: Science, 271, 213 (1996)
• Goulett, C.C., et al.: JBC, 273, 45, 30012 (1996)
• Adams, C.M., et al.: JBC, 273, 46, 30204 (1998)