1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-4-carboxylic acid

• ChemBase ID: 152810
• Molecular Formular: C26H30N2O6
• Molecular Mass: 466.5262
• Monoisotopic Mass: 466.21038669
• SMILES: CC(C)(C)OC(=O)N1CCC(CC1)(C(=O)O)NC(=O)OCC1c2ccccc2c2c1cccc2
• Canonical SMILES: O=C(NC1(CCN(CC1)C(=O)OC(C)(C)C)C(=O)O)OCC1c2ccccc2c2c1cccc2
• InChI: InChI=1S/C26H30N2O6/c1-25(2,3)34-24(32)28-14-12-26(13-15-28,22(29)30)27-23(31)33-16-21-19-10-6-4-8-17(19)18-9-5-7-11-20(18)21/h4-11,21H,12-16H2,1-3H3,(H,27,31)(H,29,30)
• InChIKey: BOFOACPQHWDRLH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-[(tert-butoxy)carbonyl]-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-4-carboxylic acid
• IUPAC Traditional name: 1-(tert-butoxycarbonyl)-4-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}piperidine-4-carboxylic acid
• Synonyms: 4-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-1,4-piperidinedicarboxylic Acid 1-(1,1-Dimethylethyl) Ester; 1-(tert-Butoxycarbonyl)-4-[[[(9H-fluoren-9-yl)methoxy]carbonyl]amino]piperidine-4-carboxylic Acid; N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic Acid; N-Boc-4-(Fmoc-amino)piperidine-4-carboxylic acid; N-Boc-4-(Fmoc-氨基)哌啶-4-羧酸

Database IDs

• CAS Number: 183673-66-7
• MDL Number: MFCD01318741
• Beilstein Number: 7609053
• PubChem SID: 24889428; 162246953
• PubChem CID: 2734399

CALCULATED PROPERTIES

• Acid pKa: 3.7690747
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 1.8995821
• LogD (pH = 7.4): 0.35533914
• Log P: 3.6316512
• Molar Refractivity: 125.2745 cm^3
• Polarizability: 49.90869 Å^3
• Polar Surface Area: 105.17 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C26H30N2O6

DETAILS

Sigma Aldrich - 90976

Other Notes
Amino acid for preparation of water-soluble highly helical peptides1
Amino acid for preparing water-soluble highly helical peptides1
Packaging
500 mg in poly tube

Toronto Research Chemicals - B619250

N-Boc-amino-(4-N-Fmoc-piperidinyl)carboxylic acid is used in the preparation of synthetic peptide amides as kappa opioid receptor agonists for treatment of pain, pruritis and inflammation associated with a variety of diseases.

REFERENCES

• Ghosh, S., et al.: J. Med. Chem., 49, 2669 (2006)