4-OXOAZETIDINE-2-CARBOXYLIC ACID

Description

4-Oxoazetidine-2-carboxylic acid may be interpreted as a cyclic mimetic of the amino acid Asp. Due to the high reactivity of the four-membered ring, this molecule can serve as an “electrophilic trap” in reactions with nucleophiles. 4-oxoazetidine-2-carboxylic acid can be used as a building block for developing enzyme inhibitors, particularly protease inhibitors. It undergoes coupling reactions with amino acids and oligopeptide esters. Following desilylation of the amino acid residue and deprotection, free β-lactam peptides are obtained^[1].

References

[1] MARTIN SCHNEIDER; Hans H O Prof Dr. β-Lactam Derivatives as Enzyme Inhibitors: Carboxy Peptidyl Derivatives of (S)-4-Oxoazetidine-2-carboxylate as Peptidomimetics[J]. Archiv der Pharmazie, 2001, 334 5: 167-172. DOI:10.1002/1521-4184(200105)334:5\<167::aid-ardp167\>3.0.CO;2-O.