(S)-4-Oxopyrrolidine-2-carboxylic acid

CAS No. 4347-18-6
Cat. No. CS-0271190
Purity≥95%
MDL No.None

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(S)-4-Oxopyrrolidine-2-carboxylic acid|CS-0271190

Structure of 4347-18-6

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Description

(S)-4-Oxopyrrolidine-2-carboxylic acid is a chiral pyrrolidine derivative featuring a ketone at the C4 position and a carboxylic acid at C2. This configuration imparts distinct stereochemical control in asymmetric synthesis, enabling its use as a building block for bioactive molecules. The molecule's rigid, electron-deficient ring system enhances binding affinity in peptidomimetic applications, while its bench-stable nature simplifies handling under standard conditions.

Application

(S)-4-Oxopyrrolidine-2-carboxylic acid serves as a versatile chiral building block in medicinal chemistry, enabling efficient access to pyrrolidine-based pharmacophores. Its enantiopure structure facilitates stereoselective synthesis of bioactive molecules, particularly in the construction of constrained peptidomimetics and heterocyclic scaffolds. The molecule exhibits good bench stability, tolerates common functional groups, and participates reliably in amide coupling, reduction, and cyclization reactions under standard conditions.

General Information

CAS No. 4347-18-6
Cat. No. CS-0271190
Purity ≥95%
MDL No. None
Storage -20°C, sealed storage, away from moisture
Shipping Room temperature in continental US; may vary elsewhere.
Molecular Formula C₅H₇NO₃
Molecular Weight 129.11
Synonym(s) 4-Oxo-L-proline
SMILES C1C(=O)CN[C@@H]1C(=O)O

Computational Chemistry Data

TPSA 66.4
LogP -0.998
H_Acceptors 3
H_Donors 2
Rotatable_Bonds 1

Safety Information

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GHS Pictogram :	GHS No : GHS07
Signal Word : Warning	UN#: N/A
Class : N/A	Packing Group : N/A
Hazard Statements : H302-H312-H332
Precautionary Statements : P261-P264-P270-P271-P280-P302+P352-P304+P340-P330-P362+P364-P501

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Other Classifications

Building Blocks Skeleton Chiral compounds Chiral Building Blocks

Life Science Amino Acids and their Derivatives Proline and derivatives

Chemical Biology Peptide Chemistry Unnatural Amino Acid Derivatives

Key Words

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(S)-4-Oxopyrrolidine-2-carboxylic acid

CAS No. 4347-18-6

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