(2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanoic acid

• ChemBase ID: 131907
• Molecular Formular: C11H21NO4
• Molecular Mass: 231.28874
• Monoisotopic Mass: 231.14705816
• SMILES: CC(C)C[C@@H](C(=O)O)NC(=O)OC(C)(C)C
• Canonical SMILES: CC(C[C@@H](C(=O)O)NC(=O)OC(C)(C)C)C
• InChI: InChI=1S/C11H21NO4/c1-7(2)6-8(9(13)14)12-10(15)16-11(3,4)5/h7-8H,6H2,1-5H3,(H,12,15)(H,13,14)/t8-/m0/s1
• InChIKey: MDXGYYOJGPFFJL-QMMMGPOBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid
• Synonyms: (S)-2-((tert-Butoxycarbonyl)amino)-4-methylpentanoic acid; N-[(1,1-Dimethylethoxy)carbonyl]-L-leucine; N-(tert-Butoxycarbonyl)-L-leucine; N-(α-tert-Butoxycarbonyl)leucine; N-Boc-L-Leucine; N-Carboxy-L-leucine N-tert-Butyl Ester; N-[(1,1-Dimethylethoxy)carbonyl]leucine; N-tert-Butoxycarbonylleucine; NSC 108690; tert-Butoxycarbonyl-L-leucine; Boc-Leu-OH; Boc-L-leucine; (2S)-2-{[(tert-butoxy)carbonyl]amino}-4-methylpentanoic acid; Boc-L-亮氨酸

Database IDs

• CAS Number: 13139-15-6
• EC Number: 236-073-2
• MDL Number: MFCD00066067
• Beilstein Number: 1711814
• PubChem SID: 162226184; 24849448
• PubChem CID: 83170

CALCULATED PROPERTIES

• Acid pKa: 4.1984906
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 0.8473822
• LogD (pH = 7.4): -0.86698675
• Log P: 2.1674962
• Molar Refractivity: 59.0439 cm^3
• Polarizability: 23.466265 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetic Acid; DMSO
• Apperance: White Solid
• Melting Point: 84-86°C; 85-90 °C; 87 - 89°C
• Optical Rotation: [α]20/D -25±0.5°, c = 2% in acetic acid
• Hydrophobicity(logP): 2.629

Safety Information

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

Product Information

• Purity: ≥99.0% (HPLC); 95%; 98%
• Ignition Residue: ≤0.05% (as SO4)
• Linear Formula: (CH3)2CHCH2CH(COOH)NHCOOC(CH3)3

DETAILS

Sigma Aldrich - 15450

Packaging
5, 25, 100 g in glass bottle

Toronto Research Chemicals - B690575

Protected amino acid with antimicrobial activity.

REFERENCES

• Oancea, S. et al.: J. Med. Biochem. 3, 239 (1999)