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

• ChemBase ID: 152504
• Molecular Formular: C19H20N2O5
• Molecular Mass: 356.3725
• Monoisotopic Mass: 356.13722175
• SMILES: c1ccc(cc1)C[C@@H](C(=O)O)NC(=O)CNC(=O)OCc1ccccc1
• Canonical SMILES: O=C(NCC(=O)N[C@H](C(=O)O)Cc1ccccc1)OCc1ccccc1
• InChI: InChI=1S/C19H20N2O5/c22-17(12-20-19(25)26-13-15-9-5-2-6-10-15)21-16(18(23)24)11-14-7-3-1-4-8-14/h1-10,16H,11-13H2,(H,20,25)(H,21,22)(H,23,24)/t16-/m0/s1
• InChIKey: FLGYJBNDDWLTQR-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-(2-{[(benzyloxy)carbonyl]amino}acetamido)-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-(2-{[(benzyloxy)carbonyl]amino}acetamido)-3-phenylpropanoic acid
• Synonyms: Z-glycyl-L-phenylalanine; Z-Gly-Phe; N-苄氧羰基甘氨酰-L-苯丙氨酸

Database IDs

• CAS Number: 1170-76-9
• EC Number: 214-626-9
• MDL Number: MFCD00037264
• Beilstein Number: 2182728
• PubChem SID: 24890278; 162246649
• PubChem CID: 6998938

CALCULATED PROPERTIES

• Acid pKa: 3.6951535
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 0.33145377
• LogD (pH = 7.4): -1.172477
• Log P: 2.1349428
• Molar Refractivity: 93.5998 cm^3
• Polarizability: 36.46475 Å^3
• Polar Surface Area: 104.73 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 125-126 °C
• Optical Rotation: [α]20/D +40±1°, c = 2.5% in ethanol

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0%
• Linear Formula: C6H5CH2OOCNHCH2CONHCH(CH2C6H5)COOH

DETAILS

Sigma Aldrich - 96260

Other Notes
Z-protected dipeptide employed in the Anteunis′ test to determine racemization in peptide coupling1
Packaging
1 g in glass bottle