14009-96-2

Usage

Uses

Used in Pharmaceutical Industry:
L-Leucine, N-acetyl-, 4-nitrophenyl ester is used as a building block for the synthesis of various pharmaceuticals, leveraging its unique properties to contribute to the development of new drugs and therapeutic agents.
Used in Biochemical Research:
In the field of biochemical research, L-Leucine, N-acetyl-, 4-nitrophenyl ester serves as a reagent in peptide synthesis, facilitating the study of protein structures, functions, and interactions.
Used in Chemical Synthesis:
L-Leucine, N-acetyl-, 4-nitrophenyl ester is employed as a reagent in the synthesis of various organic compounds, taking advantage of its unique chemical properties to create a wide range of products in the chemical industry.

Upstream product

• 6600-40-4 L-Norvaline 
• 100-02-7 4-nitro-phenol 
• 1188-21-2 N-Ac-Leu 

Downstream Products

• 100-02-7 4-nitro-phenol 

Relevant academic research and scientific papers

Oxidative Damage in Aliphatic Amino Acids and Di- and Tripeptides by the Environmental Free Radical Oxidant NO3?: the Role of the Amide Bond Revealed by Kinetic and Computational Studies

Kinetic and computational data reveal a complex behavior of the important environmental free radical oxidant NO3? in its reactions with aliphatic amino acids and di- and tripeptides, suggesting that attack at the amide N-H bond in the peptide backbone is a highly viable pathway, which proceeds through a proton-coupled electron transfer (PCET) mechanism with a rate coefficient of about 1 × 106 M-1 s-1 in acetonitrile. Similar rate coefficients were determined for hydrogen abstraction from the α-carbon and from tertiary C-H bonds in the side chain. The obtained rate coefficients for the reaction of NO3? with aliphatic di- and tripeptides suggest that attack occurs at all of these sites in each individual amino acid residue, which makes aliphatic peptide sequences highly vulnerable to NO3?-induced oxidative damage. No evidence for amide neighboring group effects, which have previously been found to facilitate radical-induced side-chain damage in phenylalanine, was found for the reaction of NO3? with side chains in aliphatic peptides.

Preparation of N-acetyl, tert-butyl amide derivatives of the 20 natural amino acids

N-Acetyl-AA(amino acid)-NHtBu derivatives of all 20 naturally occurring amino acids have been synthesized. Syntheses were performed via solution-phase methodology with yields that allow for access to gram quantities of substrates, in most cases. Syntheses include the coupling of a hindered amine, tert-butylamine, with each amino acid, either directly or in two steps using an activated ester isolated as an intermediate. The introduction of protecting groups was necessary in some cases. The development of synthetic sequences to access challenging substrates, such as the one derived from asparagine, are discussed.