78854-27-0

Basic information

• Product Name: L-Proline,4-mercapto-,hydrochloride(1:1),
• Synonyms: L-Proline,4-mercapto-,hydrochloride(1:1),;(2S,4S)-4-sulfanylpyrrolidine-2-carboxylic acid hydrochloride;(4S)-4-Mercapto-L-proline chloride
• CAS NO: 78854-27-0
• Molecular Formula: C₅H₉NO₂S*ClH
• Molecular Weight: 147.2
• Mol File: 78854-27-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: L-Proline,4-mercapto-,hydrochloride(1:1),(CAS DataBase Reference)
• NIST Chemistry Reference: L-Proline,4-mercapto-,hydrochloride(1:1),(78854-27-0)
• EPA Substance Registry System: L-Proline,4-mercapto-,hydrochloride(1:1),(78854-27-0)

Safety Data

• Hazardous Substances Data: 78854-27-0(Hazardous Substances Data)

Usage

Uses

Used in Biochemical Research:
L-Proline,4-mercapto-,hydrochloride(1:1), is used as a research compound for various biochemical studies due to its role in protein synthesis and its solubility in aqueous solutions.
Used in Pharmaceutical Industry:
In the pharmaceutical industry, L-Proline,4-mercapto-,hydrochloride(1:1), is used as an active pharmaceutical ingredient or a stabilizer in the development of drugs that target protein synthesis and wound healing processes.
Used in Biotechnological Applications:
L-Proline,4-mercapto-,hydrochloride(1:1), is utilized in biotechnology for applications such as protein crystallization, enzyme assays, and the formulation of cell culture media, given its compatibility with biological systems and its role in cellular processes.
Used in Laboratory Procedures:
L-Proline,4-mercapto-,hydrochloride(1:1), serves as a reagent in various laboratory procedures that require an amino acid with enhanced solubility and stability, supporting a wide array of experiments in molecular biology and related fields.

Upstream product

• 78854-26-9 4(S)-(benzylthio)pyrrolidine-2(S)-carboxylic acid hydrochloride 
• 57750-51-3 (3R,5S)-5-(methoxycarbonyl)-1-acetylpyrrolidin-3-yl 4-methylbenzenesulfonate 
• 78854-22-5 methyl N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxylate 
• 78854-23-6 N-acetyl-4(S)-(benzylthio)pyrrolidine-2(S)-carboxic acid 

Downstream Products

• 83624-62-8 (2S,4S)-4-(benzylsulfanyl)-pyrrolidine-2-carboxylic acid 
• 215113-34-1 (4S)-4-(4-cyclohexylbenzylthio)-L-proline 
• 1067189-38-1 (4S)-(4-tert-butyl)benzylthio-L-proline 

Relevant articles and documents

Sulfinic Acids and Related Compounds. 13. Unsymmetrical Disulfides Based on Methyl 4-Mercaptobutanesulfinate and 4(S)- or 4(R)-Mercaptoprolines

In a study of disulfide-sulfinates containing prolylthio moieties epimeric at C-4, the OH group of N-acetylated 4(R)-hydroxy-2(S)-pyrrolidinecarboxylic acid ("trans-4-hydroxy-L-proline", 3) was converted to an epimeric SH group (11) by replacing a 4-O-tosyl group with PhCH2S (to give 5) and debenzylating.Reaction of 11 as the disodium salt with 1,2-dithiane 1,1-dioxide (2) replaced the H of the SH with S(CH2)4SO2Na to give a disulfide-sulfinate salt (9).Since 9 was unstable in solution, with conversion of disodium 4,4'-trithiobis(butanesulfinate) (22) to the diester 23 as a model, 9 was converted to the disulfide-sulfinic ester 10.Subsidiary peaks in the 13C NMR spectra of N-acetyl derivatives were shown to originate from rotamers.Similarly, the epimeric 4(S)-hydroxyproline (16) was converted to the 4(R)-mercaptoproline epimer (19) of 11, which was converted in turn to the disulfide-sulfinate epimer (21) of the sulfinic ester 10.The two disulfide-sulfinate esters 10 and 21 were stable under ambient conditions and began to disproportionate to the two symmetrical disulfides in refluxing ethylacetate in 1.5 (21) to ca. 7 h (10).The sulfinic esters 10, 21, and 23 seem likely to serve as biological precursors of sulfinate and thiolate salts, which may be usefull for several purposes.