| Identification | Back Directory | [Name]
4-OXOAZETIDINE-2-CARBOXYLIC ACID | [CAS]
98019-65-9 | [Synonyms]
4-Carboxyazetidin-2-one
4-OXOAZETIDINE-2-CARBOXYLIC ACID
2-Azetidinecarboxylic acid, 4-oxo-
(2R)-2-azetidinone-4-carboxylic acid | [Molecular Formula]
C4H5NO3 | [MDL Number]
MFCD00798160 | [MOL File]
98019-65-9.mol | [Molecular Weight]
115.09 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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. |
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