L-Thioproline
[CAS# 34592-47-7]

Identification

• Classification: Biochemical >> Amino acids and their derivatives >> Proline derivatives
• Name: L-Thioproline
• Synonyms: L(-)-Thiazolidine-4-carboxylic acid
• Molecular Formula: C₄H₇NO₂S
• Molecular Weight: 133.16
• Protein Sequence: X
• CAS Registry Number: 34592-47-7
• EC Number: 252-106-3
• SMILES: C1[C@H](NCS1)C(=O)O

Properties

• Melting point: 203 °C
• alpha: -101 ° (c=1, 1N HCl)
• Water solubility: 28.5 g/L (20 °C)

Safety Data

• Hazard Symbols: GHS06;GHS07 Danger
• Risk Statements: H301-H302-H312+H332-H312-H315-H319-H332-H335
• Safety Statements: P261-P264-P264+P265-P270-P271-P280-P301+P316-P301+P317-P302+P352-P304+P340-P305+P351+P338-P317-P319-P321-P330-P332+P317-P337+P317-P362+P364-P403+P233-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Skin irritation	Skin Irrit.	2	H315
Eye irritation	Eye Irrit.	2	H319
Specific target organ toxicity - single exposure	STOT SE	3	H335
Acute toxicity	Acute Tox.	4	H332
Acute toxicity	Acute Tox.	4	H312
Acute toxicity	Acute Tox.	3	H301
Acute toxicity	Acute Tox.	4	H302
Eye irritation	Eye Irrit.	2A	H319

Discovery and Applications

L-Thioproline is a sulfur-containing analog of proline, a non-essential amino acid that plays a crucial role in protein structure and function. This compound, with the chemical formula C5H6N2O2S, is notable for its unique properties and applications in various fields, including medicinal chemistry and materials science.

The discovery of L-Thioproline dates back to the early 1960s, when it was first synthesized as part of efforts to explore new amino acid analogs with potential biological activities. The synthesis of L-Thioproline involves the substitution of the hydroxyl group in proline with a thiol group, resulting in the incorporation of sulfur into the proline structure. This modification imparts distinct chemical properties to the compound, making it an interesting subject of study for researchers.

One of the primary applications of L-Thioproline is in the field of medicinal chemistry, where it is used as a building block for the development of novel pharmaceuticals. Its unique sulfur-containing structure allows for the creation of compounds with altered biological activities compared to their non-sulfur analogs. For instance, L-Thioproline has been investigated for its potential as an inhibitor of specific enzymes and as a ligand for various biological targets. Its incorporation into peptide and protein structures can affect their stability, reactivity, and interactions with other molecules, making it a valuable tool for drug design and development.

In addition to its applications in medicinal chemistry, L-Thioproline is also used in materials science. Its chemical properties enable it to participate in various reactions that are useful for synthesizing functional materials. For example, L-Thioproline can be employed in the preparation of polymers and coordination complexes that exhibit unique physical and chemical properties. These materials can find applications in fields such as catalysis, sensor technology, and nanotechnology.

L-Thioproline is also of interest in the study of protein folding and stability. The introduction of a thiol group into a proline residue can influence the folding and stabilization of proteins, which is critical for understanding protein function and designing therapeutics that target specific protein conformations. Researchers use L-Thioproline to probe the effects of sulfur substitution on protein structure and dynamics, providing valuable insights into protein chemistry and biochemistry.

In summary, L-Thioproline is a sulfur-containing analog of proline with significant applications in medicinal chemistry, materials science, and protein research. Its unique chemical properties, derived from the incorporation of sulfur into the proline structure, make it a valuable tool for drug development, material synthesis, and the study of protein folding. The ongoing research into L-Thioproline continues to reveal new possibilities for its use in various scientific and industrial applications.

References

2020. Synthesis of Thiazolidine-4-carboxylic acid derivatives. Bioorganic & Medicinal Chemistry, 28(12).
DOI: 10.1016/j.bmc.2020.115543