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

• ChemBase ID: 53041
• Molecular Formular: C11H14N2O4
• Molecular Mass: 238.23986
• Monoisotopic Mass: 238.09535694
• SMILES: NC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• Canonical SMILES: NC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C11H14N2O4/c12-6-9(10(14)15)13-11(16)17-7-8-4-2-1-3-5-8/h1-5,9H,6-7,12H2,(H,13,16)(H,14,15)/t9-/m0/s1
• InChIKey: FOXRXVSTFGNURG-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoic acid
• IUPAC Traditional name: (2S)-3-amino-2-{[(benzyloxy)carbonyl]amino}propanoic acid
• Synonyms: (S)-3-Amino-2-(benzyloxycarbonylamino)-propanoic acid; 3-Amino-N-[(phenylmethoxy)carbonyl]-L-alanine; CBZ-L-β-Aminoalanine; (S)-2-(Benzyloxycarbonylamino)-3-aminopropionic Acid; Nα-Carbobenzyloxy-β-amino-L-alanine; Z-Dpr-OH; Nα-Z-L-2,3-Diaminopropionic acid; Z-Dap-OH; Nα-苄氧羰基-L-2,3-二氨基丙酸

Database IDs

• CAS Number: 35761-26-3
• MDL Number: MFCD00237345
• Beilstein Number: 4486950
• PubChem SID: 162057804; 24890256
• PubChem CID: 2756313

CALCULATED PROPERTIES

• Acid pKa: 3.1277213
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -1.8339537
• LogD (pH = 7.4): -1.8378004
• Log P: -1.8330592
• Molar Refractivity: 59.3785 cm^3
• Polarizability: 23.530632 Å^3
• Polar Surface Area: 101.65 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dilute Acid
• Apperance: White Solid
• Melting Point: ~240 °C (dec.); 219-221°C dec.
• Optical Rotation: [α]20/D -39±1°, c = 1% in 1 M HCl

Safety Information

• Storage Condition: Refrigerator
• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (NT); 95%
• Linear Formula: H2NCH2CH(NHCO2CH2C6H5)CO2H

DETAILS

Sigma Aldrich - 96085

Other Notes
Important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins1,2,3
Packaging
5 g in glass bottle

Toronto Research Chemicals - C176175

Important building block for the synthesis of peptides containing DAP residues, e.g. bleomycins, edeines, tuberactinomycins.

REFERENCES

• Thuring, J., et al.: Biochem., 41, 2002 (2002)
• Hausch, F., et al.: Chem. Biol., 10, 225 (2002)
• Palucki, B., et al.: Bioorg. Med. Chem. Lett.,15, 1993 (2002)