4-OXOAZETIDINE-2-CARBOXYLIC ACID Chemical Properties

Boiling point:

489.4±38.0 °C(Predicted)

Density 

1.519±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

3.19±0.20(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C4H5NO3/c6-3-1-2(5-3)4(7)8/h2H,1H2,(H,5,6)(H,7,8)

InChIKey

YSPMLLKKKHCTBN-UHFFFAOYSA-N

SMILES

N1C(=O)CC1C(O)=O

Safety Information

HazardClass 

IRRITANT

4-OXOAZETIDINE-2-CARBOXYLIC ACID Usage And Synthesis

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.