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

• ChemBase ID: 102115
• Molecular Formular: C13H15NO6
• Molecular Mass: 281.2613
• Monoisotopic Mass: 281.08993721
• SMILES: OC(=O)CC[C@H](NC(=O)OCc1ccccc1)C(=O)O
• Canonical SMILES: O=C(N[C@H](C(=O)O)CCC(=O)O)OCc1ccccc1
• InChI: InChI=1S/C13H15NO6/c15-11(16)7-6-10(12(17)18)14-13(19)20-8-9-4-2-1-3-5-9/h1-5,10H,6-8H2,(H,14,19)(H,15,16)(H,17,18)/t10-/m0/s1
• InChIKey: PVFCXMDXBIEMQG-JTQLQIEISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioic acid
• IUPAC Traditional name: (2S)-2-{[(benzyloxy)carbonyl]amino}pentanedioic acid
• Synonyms: CARBOBENZOXY-L-GLUTAMIC ACID; (S)-2-(((benzyloxy)carbonyl)amino)pentanedioic acid; N-[(Phenylmethoxy)carbonyl]-L-glutamic Acid; N-CBz-L-Glutamic Acid; Benzyloxycarbonyl-L-Glutamic Acid; Carbobenzoxy-L-glutamic Acid; N-Carbobenzoxy-L-glutamic Acid; NSC 555; NSC 88494; N-Carbobenzyloxy-L-glutamic Acid; N-Benzyloxycarbonyl-L-glutamic acid; N-(Carbobenzyloxy)-L-glutamic acid; Z-L-Glutamic acid; Z-Glu-OH; N-CBZ-L-GLUTAMIC ACID; Z-Glu-OH; N-苄氧羰基-L-谷氨酸; N-苄氧羰基-L-谷氨酸; 苄氧羰基-L-谷氨酸

Database IDs

• CAS Number: 1155-62-0
• EC Number: 214-584-1
• MDL Number: MFCD00002801
• Beilstein Number: 2061272
• PubChem SID: 24888482; 162088415
• PubChem CID: 70866

CALCULATED PROPERTIES

• Acid pKa: 3.3612714
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -2.3186991
• LogD (pH = 7.4): -5.3282924
• Log P: 1.2307489
• Molar Refractivity: 66.9677 cm^3
• Polarizability: 26.296143 Å^3
• Polar Surface Area: 112.93 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; Methanol
• Apperance: Off-White Solid
• Melting Point: 108-116°C; 115-117 °C(lit.)
• Optical Rotation: [α]22/D -7.4°, c = 10 in acetic acid; -7.5 (c=4 in acetic acid)

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• TSCA Listed: 是
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: 99%
• Linear Formula: HOOCCH2CH2CH(NHCOOCH2C6H5)COOH

DETAILS

MP Biomedicals - 05203817

MP Biomedicals Rare Chemical collection

MP Biomedicals - 02100215

Crystalline

Sigma Aldrich - 859060

Packaging
25 g in glass bottle

Toronto Research Chemicals - C176510

Used for the synthesis of carboxyalkyl peptides as inhibitors of angiotensin-converting enzyme of human blood serum.

REFERENCES

• Anderson, A., et al.: Chem. Biol., 8, 445 (2001)
• Claussen, H., et al.: J. Mol. Biol., 308, 377 (2001)
• Sherman, W., et al.: J. Med. Chem., 49, 534 (2001)