(S)-3-(benzylamino)-2-(((benzyloxy)carbonyl)amino)propanoic acid
$450.00
CAS No.: 160885-24-5
Catalog No.: 196581
Purity: 95%
MF: C18H20N2O4
MW: 328.368
Storage: 2-8 degree Celsius
SMILES: C(C1=CC=CC=C1)NC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
Catalog No.: 196581
Purity: 95%
MF: C18H20N2O4
MW: 328.368
Storage: 2-8 degree Celsius
SMILES: C(C1=CC=CC=C1)NC[C@@H](C(=O)O)NC(=O)OCC1=CC=CC=C1
(S)-3-(benzylamino)-2-(((benzyloxy)carbonyl)amino)propanoic acid; CAS No.: 160885-24-5; (S)-3-(benzylamino)-2-(((benzyloxy)carbonyl)amino)propanoic acid. PROPERTIES: This amino acid derivative is a white crystalline powder with molecular formula C16H19N3O4. It has molecular weight of 325.34 g/mol and melting point between 135-140 C. The compound is moderately soluble in methanol and water but has limited solubility in non-polar solvents. Recommended storage is in tightly sealed containers at 2-8 C to prevent hydrolysis of the carbamate group. Being an amine and acid containing compound, it may cause skin and eye irritation; standard laboratory safety practices should be observed. APPLICATIONS: In peptide synthesis, this compound serves as protected amino acid building block for constructing bioactive peptides. The (S)-configuration matches natural amino acid stereochemistry, enabling native peptide bond formation (Journal of Peptide Research). The benzyloxycarbonyl group protects the alpha-amino group, which can be removed by hydrogenolysis using palladium catalyst. Additionally, it functions as intermediate for producing beta-lactam antibiotics where the three-membered azetidine ring is formed from this precursor through intramolecular cyclization (Journal of Antibiotics). The benzylamino group provides additional steric and electronic effects that influence peptide conformation and binding properties. These applications highlight its utility as versatile chiral building block in medicinal chemistry.
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