4-{[(tert-butoxy)carbonyl]amino}-1-hydroxy-2,2,6,6-tetramethylpiperidine-4-carboxylic acid

• ChemBase ID: 162651
• Molecular Formular: C15H28N2O5
• Molecular Mass: 316.39322
• Monoisotopic Mass: 316.19982201
• SMILES: C1C(N(C(CC1(NC(=O)OC(C)(C)C)C(=O)O)(C)C)O)(C)C
• Canonical SMILES: O=C(NC1(CC(C)(C)N(C(C1)(C)C)O)C(=O)O)OC(C)(C)C
• InChI: InChI=1S/C15H28N2O5/c1-12(2,3)22-11(20)16-15(10(18)19)8-13(4,5)17(21)14(6,7)9-15/h21H,8-9H2,1-7H3,(H,16,20)(H,18,19)
• InChIKey: PEFAGYOGVDZSOM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-{[(tert-butoxy)carbonyl]amino}-1-hydroxy-2,2,6,6-tetramethylpiperidine-4-carboxylic acid
• IUPAC Traditional name: 4-[(tert-butoxycarbonyl)amino]-1-hydroxy-2,2,6,6-tetramethylpiperidine-4-carboxylic acid
• Synonyms: 4-Carboxy-4-[[(1,1-dimethylethoxy)carbonyl]amino]-2,2,6,6-tetramethyl-1-piperidinyloxy; N-Boc-TOAC; N-Boc-2,2,6,6-tetramethylpiperidine-N-oxyl-4-amino-4-carboxylic Acid

Database IDs

• CAS Number: 124843-12-5
• PubChem SID: 162256786
• PubChem CID: 71314175

CALCULATED PROPERTIES

• Acid pKa: 4.0936236
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): -0.2069164
• LogD (pH = 7.4): -1.8840069
• Log P: 1.092975
• Molar Refractivity: 80.9512 cm^3
• Polarizability: 32.2637 Å^3
• Polar Surface Area: 99.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Solid
• Melting Point: >150°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - B667850

Used in the synthesis of peptides containing TOAC, a spin-labeled Cα,α-disubstituted glycine.

REFERENCES

• Wintjens, R., et al.: J. Mol. Biol., 255, 235 (1996)
• Mitra, J., et al.: Int. J. Pept. Protein. Res., 9, 27 (1996)
• Broda, M., et al.: J. Pept. Sci., 10, 448 (1996)