65167-28-4

Basic information

• Product Name: (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline
• Synonyms: (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline;N-(3-ACETYLTHIO-2R-METHYLPROPIONYL)-L-PROLINE;N-(3-ACETYLTHIO-2R-METHYLPROPIONYL)-L-PROLINECAPTOPRIL;1-[(R)-3-(Acetylthio)-2-methyl-1-oxopropyl]-L-proline;Captopril Related Compound 7
• CAS NO: 65167-28-4
• Molecular Formula: C₁₁H₁₇NO₄S
• Molecular Weight: 259.32198
• EINECS: 265-586-4
• Mol File: 65167-28-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 464.8°C at 760 mmHg
• Flash Point: 234.9°C
• Appearance: /
• Density: 1.291g/cm³
• Vapor Pressure: 6.32E-10mmHg at 25°C
• Refractive Index: 1.548
• CAS DataBase Reference: (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline(65167-28-4)
• EPA Substance Registry System: (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline(65167-28-4)

Safety Data

• Hazardous Substances Data: 65167-28-4(Hazardous Substances Data)

Usage

General Description

(R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline, also known as acetylthio-2-methylproline, is a chemical compound with the molecular formula C9H15NO3S. It is a derivative of proline, an amino acid that is important for the structure and function of proteins. (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline contains an acetylthio group, which is a sulfur-containing functional group, and a methyl group, and it is classified as a thiol. (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline may have potential applications in organic synthesis, pharmaceuticals, and biochemical research due to its unique structure and properties. Further studies and research are needed to fully understand the potential uses and effects of (R)-1-[3-(acetylthio)-2-methyl-1-oxopropyl]-L-proline.

InChI:InChI=1/C11H17NO4S/c1-7(6-17-8(2)13)10(14)12-5-3-4-9(12)11(15)16/h7,9H,3-6H2,1-2H3,(H,15,16)/t7-,9-/m0/s1

Upstream product

• 74431-52-0 (R)-3-acetylsulfanyl-2-methyl-propionic acid 
• 69570-39-4 (S)-(-)-3-acetylthio-2-methylpropionyl chloride 
• 147-85-3 L-proline 
• 51161-88-7 N-methacryloyl-L-proline 
• 507-09-5 tiolacetic acid 

Downstream Products

• 63250-36-2 captopril 
• 64838-55-7 (2S)-1-[(2S)-3-acetylthio-2-methylpropanoyl]pyrrolidine-2-carboxylic acid 

Relevant articles and documents

Structural basis of metallo-β-lactamase inhibition by captopril stereoisomers

β-Lactams are the most successful antibacterials, but their effectiveness is threatened by resistance, most importantly by production of serine- and metallo-β-lactamases (MBLs). MBLs are of increasing concern because they catalyze the hydrolysis of almost all β-lactam antibiotics, including recent-generation carbapenems. Clinically useful serine-β-lactamase inhibitors have been developed, but such inhibitors are not available for MBLs. L-Captopril, which is used to treat hypertension via angiotensin-converting enzyme inhibition, has been reported to inhibit MBLs by chelating the active site zinc ions via its thiol(ate). We report systematic studies on B1 MBL inhibition by all four captopril stereoisomers. High-resolution crystal structures of three MBLs (IMP-1, BcII, and VIM-2) in complex with either the L- or D-captopril stereoisomer reveal correlations between the binding mode and inhibition potency. The results will be useful in the design of MBL inhibitors with the breadth of selectivity required for clinical application against carbapenem-resistant Enterobacteriaceae and other organisms causing MBL-mediated resistant infections.