(2S)-4-carbamoyl-2-dodecanamidobutanoic acid

• ChemBase ID: 172245
• Molecular Formular: C17H32N2O4
• Molecular Mass: 328.44698
• Monoisotopic Mass: 328.23620751
• SMILES: NC(=O)CC[C@H](NC(=O)CCCCCCCCCCC)C(=O)O
• Canonical SMILES: CCCCCCCCCCCC(=O)N[C@H](C(=O)O)CCC(=O)N
• InChI: InChI=1S/C17H32N2O4/c1-2-3-4-5-6-7-8-9-10-11-16(21)19-14(17(22)23)12-13-15(18)20/h14H,2-13H2,1H3,(H2,18,20)(H,19,21)(H,22,23)/t14-/m0/s1
• InChIKey: USMCNVFGYLZLGM-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-4-carbamoyl-2-dodecanamidobutanoic acid
• IUPAC Traditional name: (2S)-4-carbamoyl-2-dodecanamidobutanoic acid
• Synonyms: N2-(1-Oxododecyl)-L-glutamine; N2-Lauroyl-L-glutamine; (2S)-4-carbamoyl-2-dodecanamidobutanoic acid

Database IDs

• CAS Number: 109570-04-9
• MDL Number: MFCD00216729
• PubChem SID: 164228155
• PubChem CID: 16213882

CALCULATED PROPERTIES

• Acid pKa: 3.93967
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 1.2141879
• LogD (pH = 7.4): -0.41096258
• Log P: 2.7816958
• Molar Refractivity: 88.5896 cm^3
• Polarizability: 34.999523 Å^3
• Polar Surface Area: 109.49 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 131 - 133°C; 132-134°C
• Hydrophobicity(logP): 3.104

Safety Information

• Storage Condition: Refrigerator

Product Information

• Purity: 95%

DETAILS

Toronto Research Chemicals - L178650

N2-Lauroyl-L-glutamine is used as a solubilizing detergent in a novel protein refolding system. N2-Lauroyl-L-glutamine can be synthesized enzymatically in glycerol-water system useing acylase I from pig kidney.

REFERENCES

• Kudou, M. et al.: Protein Express. Purif., 75, 46 (2011)
• Wada, E. et al.: J. Am. Oil Chem. Soc., 79, 41 (2011)