3190-70-3

Basic information

• Product Name: (S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE
• Synonyms: (S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE;(S)-4-ISOBUTYL-OXAZOLIDINE-2,5-DIONE;L-Leucine N-carboxyanhydride;(4S)-4β-(2-Methylpropyl)oxazolidine-2,5-dione;(S)-4β-(2-Methylpropyl)-2,5-oxazolidinedione;L-Leucine NCA;N-Carboxy-L-leucine anhydride;L-Leu-NCA
• CAS NO: 3190-70-3
• Molecular Formula: C₇H₁₁NO₃
• Molecular Weight: 157.17
• EINECS: 221-692-2
• Mol File: 3190-70-3.mol
• Article Data: 45

Chemical Properties

• Melting Point: 76-77°C
• Appearance: /
• Density: 1.125 g/cm³
• Refractive Index: 1.451
• Storage Temp.: Inert atmosphere,Room Temperature
• PKA: 9.38±0.40(Predicted)
• CAS DataBase Reference: (S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE(3190-70-3)
• EPA Substance Registry System: (S)-(-)-4-ISOBUTYLOXAZOLIDINE-2,5-DIONE(3190-70-3)

Safety Data

• Safety Statements: 22-24/25
• Hazardous Substances Data: 3190-70-3(Hazardous Substances Data)

Usage

Uses

N-Carboxyleucine Anhydride is a reagent in the synthesis of hybrid polypeptide micelles which are used to load indocyanine green dyes into lab rats for tumor imaging and photothermal effect studies.

InChI:InChI=1/C7H11NO3/c1-4(2)3-5-6(9)11-7(10)8-5/h4-5H,3H2,1-2H3,(H,8,10)/t5-/m0/s1

Upstream product

• 61-90-5 L-leucine 
• 24424-95-1 di-tert-butyl tricarbonate 
• 328-38-1 (R)-leucine 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 42534-05-4 N-carbamoyl-DL-leucine 
• 328-39-2 LEUCINE 
• 75-44-5 phosgene 
• 61-90-5 L-leucine 
• 15984-97-1 leucine 
• 2018-66-8 N-carbobenzyloxy leucine 
• 117919-56-9 methoxycarbonyl-dl-leucine 
• 503-38-8 trichloromethyl chloroformate 
• 114488-94-7 H-D-Leu-OH 
• 13139-15-6 N-tert-butoxycarbonyl-L-leucine 

Downstream Products

• 54745-19-6 4-isobutyl-3-(2-nitro-phenylsulfanyl)-oxazolidine-2,5-dione 
• 462-60-2 N-carbamoylglycine 
• 3063-05-6 Leu-Phe-OH 
• 125814-21-3 (S)-4-Isobutyl-2,5-dioxo-oxazolidine-3-carboxylic acid 9H-fluoren-9-ylmethyl ester 
• 75779-22-5 H-Leu-Ala-OH 
• 77167-53-4 HCl*H-Leu₂-OBn 
• 47094-27-9 H-Leu-Gly-OBzl 
• 84111-39-7 L-leucyl-L-valine benzyl ester 
• 66900-32-1 (S)-2-Amino-4-methyl-pentanoic acid [(2S,3S,4S,6R)-6-((1S,3S)-3-acetyl-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-1-yloxy)-3-hydroxy-2-methyl-tetrahydro-pyran-4-yl]-amide 
• 142380-48-1 (S)-2-(3-Cyclohexyl-ureido)-4-methyl-pentanoic acid 
• 1141472-21-0 C₁₈H₂₆N₂O₅ 
• 686-50-0 L-leucyl-glycine 
• 7298-84-2 Leu-Ala 
• 55903-68-9 Nps-L-Leu-NCA 

Relevant articles and documents

Cooperative hierarchical self-assembly of peptide dendrimers and linear polypeptides into nanoarchitectures mimicking viral capsids

Peptidesomes are nanoparticles that are built by a two-step self-assembly of globular peptide dendrimers with lysine endgroups (red spheres in picture) and poly(L-leucine) carrying one glutamic acid residue (blue lines with red dot). These viral-capsid-mimicking nanoarchitectures exhibit high gene transfection efficacy and thus are promising nonviral vectors for biomedical applications. Copyright

A scalable synthesis of L-leucine-N-carboxyanhydride

Due to its relevance in the synthesis of well-defined oligopeptides, the L-leucine-N-carboxyanhydride (leucine-NCA) synthesis was selected for fine chemical scale-up with a scope on application on larger scales. The heterogeneous gas-solid-liquid nature of the leucine-NCA synthesis implied a mass transfer limited reaction rate towards phosgenation and was investigated on bench scale. Upon scale increase, the liquid-gas mass transport of HCl is drastically reduced, retarding the reaction and consequently rendering the process unsuitable for scale-up. Addition of an HCl scavenger such as (+)-limonene prevented side reactions thus allowing a cost reduction, a considerably faster reaction, and minimization of the amount of phosgene source used. The modified leucine-NCA synthesis has successfully been made scalable, maintaining high product purity on a 1.0 dm3 scale.

Synthesis of α-Amino Acid N-Carboxyanhydrides

A simple phosgene- and halogen-free method for synthesizing α-amino acid N-carboxyanhydrides (NCAs) is described. The reaction between Boc-protected α-amino acids and T3P reagent gave the corresponding NCA derivatives in good yield and purity with no detectable epimerization. The process is safe, is easy-to-operate, and does not require any specific installation. It generates nontoxic, easy to remove byproducts. It can apply to the preparation of NCAs for the on-demand on-site production of either little or large quantities.

METHOD FOR PRODUCING AMINO ACID-N-CARBOXYLIC ACID ANHYDRIDE

PROBLEM TO BE SOLVED: To provide: a method for safely and efficiently producing amino acid-N-carboxylic acid anhydride; and a method for producing peptide by using the obtained amino acid-N-carboxylic acid anhydride. SOLUTION: The method for producing an amino acid-N-carboxylic acid anhydride according to the present invention is characterized in that the amino acid-N-carboxylic acid anhydride is represented by the following formula (II), and a step of irradiating a composition containing a halogenated methane and an amino acid compound represented by the following formula (I) with high energy light in the presence of oxygen is included. [In the formula, R1 represents an amino acid side chain group in which the reactive group is protected, and R2 represents H or the like.]. SELECTED DRAWING: None COPYRIGHT: (C)2020,JPOandINPIT