(2S)-2,6-di{[(benzyloxy)carbonyl]amino}hexanoic acid

• ChemBase ID: 131630
• Molecular Formular: C22H26N2O6
• Molecular Mass: 414.45164
• Monoisotopic Mass: 414.17908656
• SMILES: c1ccc(cc1)COC(=O)NCCCC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• Canonical SMILES: O=C(OCc1ccccc1)NCCCC[C@@H](C(=O)O)NC(=O)OCc1ccccc1
• InChI: InChI=1S/C22H26N2O6/c25-20(26)19(24-22(28)30-16-18-11-5-2-6-12-18)13-7-8-14-23-21(27)29-15-17-9-3-1-4-10-17/h1-6,9-12,19H,7-8,13-16H2,(H,23,27)(H,24,28)(H,25,26)/t19-/m0/s1
• InChIKey: BLZXFNUZFTZCFD-IBGZPJMESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2,6-di{[(benzyloxy)carbonyl]amino}hexanoic acid
• IUPAC Traditional name: (2S)-2,6-di{[(benzyloxy)carbonyl]amino}hexanoic acid
• Synonyms: Z-Lys(Z)-OH; N,N′-Di-Cbz-L-lysine; Nα,Nε-Di-Z-L-lysine; N2,N6-Bis[(phenylmethoxy)carbonyl]-L-lysine; N,N'-Bis(benzyloxycarbonyl)-L-lysine; N2,N6-Dicarbobenzoxy-L-lysine; NSC 88474; N2,N6-Bis(benzyloxycarbonyl)-L-lysine; Z-Lys(Z)-OH; N,N′-双苄氧羰基-L-赖氨酸; Nα,Nε-二-Z-L-赖氨酸

Database IDs

• CAS Number: 405-39-0
• EC Number: 206-971-9
• MDL Number: MFCD00037822
• Beilstein Number: 1897206
• PubChem SID: 162225907; 24890354
• PubChem CID: 7269422

CALCULATED PROPERTIES

• Acid pKa: 3.637827
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.7557561
• LogD (pH = 7.4): 0.28514734
• Log P: 3.6146097
• Molar Refractivity: 109.1695 cm^3
• Polarizability: 42.684494 Å^3
• Polar Surface Area: 113.96 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White Solid

Safety Information

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

Product Information

• Purity: ≥98.0% (TLC); 95+%
• Linear Formula: C6H5CH2O2CNH(CH2)4CH(NHCO2CH2C6H5)CO2H

DETAILS

Sigma Aldrich - 96835

Packaging
5 g in poly bottle

Toronto Research Chemicals - B410905

Protected L-lysine

REFERENCES

• Yang, C., et al.: J. Pharm. Sci., 90, 617 (2001)
• Yamashita, A., et al.: Bioorg. Med. Chem. Lett., 13, 3345 (2001)
• Vangapandu, S., et al.: Bioorg. Med. Chem., 12, 239 (2001)