1,5-dibenzyl (2S)-2-[(2S)-2-aminopropanamido]pentanedioate

• ChemBase ID: 159613
• Molecular Formular: C22H26N2O5
• Molecular Mass: 398.45224
• Monoisotopic Mass: 398.18417194
• SMILES: c1(COC(=O)CC[C@@H](C(=O)OCc2ccccc2)NC(=O)[C@@H](N)C)ccccc1
• Canonical SMILES: O=C(CC[C@@H](C(=O)OCc1ccccc1)NC(=O)[C@@H](N)C)OCc1ccccc1
• InChI: InChI=1S/C22H26N2O5/c1-16(23)21(26)24-19(22(27)29-15-18-10-6-3-7-11-18)12-13-20(25)28-14-17-8-4-2-5-9-17/h2-11,16,19H,12-15,23H2,1H3,(H,24,26)/t16-,19-/m0/s1
• InChIKey: UQRIFZCMNCZLJQ-LPHOPBHVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1,5-dibenzyl (2S)-2-[(2S)-2-aminopropanamido]pentanedioate
• IUPAC Traditional name: 1,5-dibenzyl (2S)-2-[(2S)-2-aminopropanamido]pentanedioate
• Synonyms: L-Alanyl-L-glutamic Acid Bis(phenylmethyl) Ester; N-L-Alanyl-L-glutamic Acid Bis(phenylmethyl) Ester; N-L-Alanyl-L-glutamic Acid Bis(benzyl) Ester

Database IDs

• CAS Number: 87063-91-0
• PubChem SID: 162253748
• PubChem CID: 67676282

CALCULATED PROPERTIES

• Acid pKa: 12.233695
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.38153443
• LogD (pH = 7.4): 1.2459974
• Log P: 2.2723534
• Molar Refractivity: 107.3485 cm^3
• Polarizability: 42.60219 Å^3
• Polar Surface Area: 107.72 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A511000

N-L-Alanyl-L-glutamic Acid Bis(benzyl) Ester is used in the preparation of alanine-glutamic dendrimer and other polypetides.

REFERENCES

• Xia, X.-Y. et al.: Zhong. Xin. Zaz., 20, 1813 (2011)