(2S)-2-[(2S)-2-[(2S)-2-[(2-aminophenyl)formamido]-4-methylpentanamido]-3-phenylpropanamido]-6-[(2,4-dinitrophenyl)amino]hexanoic acid; trifluoroacetic acid

• ChemBase ID: 154000
• Molecular Formular: C36H42F3N7O11
• Molecular Mass: 805.7541896
• Monoisotopic Mass: 805.28943986
• SMILES: CC(C)C[C@@H](C(=O)N[C@@H](Cc1ccccc1)C(=O)N[C@@H](CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])C(=O)O)NC(=O)c1ccccc1N.C(=O)(C(F)(F)F)O
• Canonical SMILES: OC(=O)C(F)(F)F.CC(C[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)O)CCCCNc1ccc(cc1[N+](=O)[O-])[N+](=O)[O-])Cc1ccccc1)NC(=O)c1ccccc1N)C
• InChI: InChI=1S/C34H41N7O9.C2HF3O2/c1-21(2)18-28(38-31(42)24-12-6-7-13-25(24)35)32(43)39-29(19-22-10-4-3-5-11-22)33(44)37-27(34(45)46)14-8-9-17-36-26-16-15-23(40(47)48)20-30(26)41(49)50;3-2(4,5)1(6)7/h3-7,10-13,15-16,20-21,27-29,36H,8-9,14,17-19,35H2,1-2H3,(H,37,44)(H,38,42)(H,39,43)(H,45,46);(H,6,7)/t27-,28-,29-;/m0./s1
• InChIKey: BAXBDLHYKKDHEJ-BJRQXHFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2S)-2-[(2S)-2-[(2-aminophenyl)formamido]-4-methylpentanamido]-3-phenylpropanamido]-6-[(2,4-dinitrophenyl)amino]hexanoic acid; trifluoroacetic acid
• IUPAC Traditional name: (2S)-2-[(2S)-2-[(2S)-2-[(2-aminophenyl)formamido]-4-methylpentanamido]-3-phenylpropanamido]-6-[(2,4-dinitrophenyl)amino]hexanoic acid; trifluoroacetic acid
• Synonyms: O-Aminobenzoic acid-Leu-Phe-Lys(DNP)-OH trifluoroacetate salt; Abz-LFK(Dnp)-OH trifluoroacetate salt; O-Aminobenzoic acid-Leu-Phe-Lys(DNP)-OH 三氟乙酸盐; Abz-LFK(Dnp)-OH 三氟乙酸盐

Database IDs

• MDL Number: MFCD11045275
• PubChem SID: 162248139
• PubChem CID: 71311772

CALCULATED PROPERTIES

• Acid pKa: 3.4920683
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): 3.138195
• LogD (pH = 7.4): 1.8205199
• Log P: 4.881304
• Molar Refractivity: 186.494 cm^3
• Polarizability: 69.04604 Å^3
• Polar Surface Area: 254.29 Å^2
• Rotatable Bonds: 20
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >2 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C34H41N7O9 · xC2HF3O2 · yH2O

DETAILS

Sigma Aldrich - A5855

Amino Acid Sequence
Abz-Leu-Phe-Lys-DNP
Biochem/physiol Actions
Abz-LFK(Dnp)-OH is an Angiotensin Converting Enzyme (ACE) fluorescent peptide substrate specific for the C domain for real time fluorescent assay (ACE, Peptidyl Dipeptidase, Kininase II, E.C. 3.4.15.1).
Application
Abz-LFK(Dnp)-OH trifluoroacetate (TFA) salt is an Angiotensin Converting Enzyme (ACE) fluorescent peptide substrate that binds specifically to the C domain of ACE. Abz-LFK(Dnp)-OH TFA has been used to study the development of new antibacterial calixarene derivatives, as well as the efficacy and toxicity of the antimicrobial peptide M33 as a possible antimicrobial agent in lung infections and sepsis.