76391-12-3

Basic information

• Product Name: 1-(1,2-DIOXOPROPYL)-S-PROLINE
• Synonyms: 1-(1,2-DIOXOPROPYL)-S-PROLINE;Dioxopropyl proline
• CAS NO: 76391-12-3
• Molecular Formula: C₈H₁₁NO₄
• Molecular Weight: 185.18
• Mol File: 76391-12-3.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 360.296 °C at 760 mmHg
• Flash Point: 171.701 °C
• Appearance: /
• Density: 1.353 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• CAS DataBase Reference: 1-(1,2-DIOXOPROPYL)-S-PROLINE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(1,2-DIOXOPROPYL)-S-PROLINE(76391-12-3)
• EPA Substance Registry System: 1-(1,2-DIOXOPROPYL)-S-PROLINE(76391-12-3)

Safety Data

• Hazardous Substances Data: 76391-12-3(Hazardous Substances Data)

Usage

General Description

1-(1,2-Dioxopropyl)-S-proline is a chemical compound consisting of a proline molecule attached to a 1,2-dioxopropyl functional group. It is also known as 1-(2-oxo-1,3-propandiol)-S-proline and has the molecular formula C8H13NO5. 1-(1,2-DIOXOPROPYL)-S-PROLINE is a derivative of proline, which is an amino acid that is important for the synthesis of proteins in the body. 1-(1,2-Dioxopropyl)-S-proline is used in organic synthesis and biochemical research, and its unique structure makes it potentially useful in the development of pharmaceuticals and other biologically active compounds.

InChI:InChI=1/C8H11NO4/c1-5(10)7(11)9-4-2-3-6(9)8(12)13/h6H,2-4H2,1H3,(H,12,13)/t6-/m0/s1

Upstream product

• 52060-81-8 N-pyruvoyl-L-proline-t-butyl ester 
• 10076-48-9 methyl 2,2-dimethoxypropionate 
• 7664-93-9 sulfuric acid 
• 7732-18-5 water 
• 147-85-3 L-proline 
• 16652-71-4 benzyl (2S)-2-pyrrolidinecarboxylate hydrochloride 
• 108415-26-5 N-(2-Oxopropionyl)prolin-benzylester 

Downstream Products

• 13485-59-1 L-alanyl-L-proline 
• 137155-61-4 N-(1-ethoxycarbonyl-2-phenylpropyl)-DL-alanyl-L-proline 
• 137219-37-5 dehydrodidemnin B 

Relevant articles and documents

Intracellular oxidation of dipeptides. Base-promoted elimination from N-halodipeptides to 2-[N-alkyl-N-(2-N- alkylimino-2-alkyl-ethanoyl)amino]-2,2-dialkylethanoic acids

One of the possible ways of intracellular oxidation of peptides is via the formation of the corresponding (N-X)-dipeptides, that then undergo base-promoted elimination to yield intermediate 2-[N-alkyl-N-(2-N-alkylimino-2-alkylethanoyl)amino]-2,2-dialkylethanoic acids, which subsequently hydrolyze. Such an elimination process is general-base catalyzed, with Bronsted β values ranging from 0.26 to 0.31, which suggests an essentially constant degree of proton transfer at the TS. For (N-X)-dipeptides, the ratio kN-Br/kN-Cl ranges from 2.5 to 15, suggesting a structural dependence of the degree of N-X bond breaking at the TS. The values of β and kN-Br/kN-Cl support a concerted asynchronous AxhDHDN mechanism, its TS changing from reactant-like to slightly nitrenium-like depending on the structure of the starting dipeptide. As a consequence of the antiperiplanarity requirements of the reaction, the steric interaction between the leaving group and the substituent on the C bearing the H to be eliminated controls the reaction rate. Such steric interaction is rather important, as indicated by the steric crossed-interaction coefficient (pssy = 0.33). Semiempirical calculations show that bulky substituents in the vicinity of the reaction center imply additional energy requirements for the system to achieve the antiperiplanarity needed at the TS for the reaction to proceed. From the observations reported it follows that (N-X)-dipeptides lose their oxidizing power more readily than analogous (N-X)-amino acids or (N-X)-amines, opening a possible pathway to lessen intracellular halogen-based oxidative stress.

Total synthesis of dehydrodidemnin B. Use of uronium and phosphonium salt coupling reagents in peptide synthesis in solution

New total syntheses of didemnin A and of dehydrodidemnin B are described. The latter didemnin has the highest antiproliferative activity of all members of this family of macrocyclic depsipeptides. It was produced on coupling the side chain Pyr-Pro-OH to d

Novel complex amido and imido derivatives of carboxyalkyl peptides

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