(2R)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoic acid

• ChemBase ID: 155169
• Molecular Formular: C17H17NO4
• Molecular Mass: 299.32118
• Monoisotopic Mass: 299.11575803
• SMILES: c1ccc(cc1)C[C@H](C(=O)O)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(N[C@@H](C(=O)O)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C17H17NO4/c19-16(20)15(11-13-7-3-1-4-8-13)18-17(21)22-12-14-9-5-2-6-10-14/h1-10,15H,11-12H2,(H,18,21)(H,19,20)/t15-/m1/s1
• InChIKey: RRONHWAVOYADJL-OAHLLOKOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoic acid
• IUPAC Traditional name: (2R)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoic acid
• Synonyms: N-Cbz-D-phenylalanine; Z-D-phenylalanine; Z-D-Phe-OH

Database IDs

• CAS Number: 2448-45-5
• MDL Number: MFCD00063151
• Beilstein Number: 4355833
• PubChem SID: 24892665; 162249307; 24890374
• PubChem CID: 675678

CALCULATED PROPERTIES

• Acid pKa: 3.8783662
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.6136721
• LogD (pH = 7.4): 0.0155921485
• Log P: 3.2402258
• Molar Refractivity: 80.7963 cm^3
• Polarizability: 31.54406 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C17H17NO4

DETAILS

Sigma Aldrich - C4127

Application
N-Cbz-D-phenylalanine is used for affinity chromatography of proteinases such as the extracellular fibrinogenolytic enzyme of Aspergillus fumigatus.