49873-82-7

Basic information

• Product Name: C₁₄H₁₉NO₅
• Synonyms: C₁₄H₁₉NO₅
• CAS NO: 49873-82-7
• Molecular Weight: 281.309
• Mol File: 49873-82-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₄H₁₉NO₅(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₄H₁₉NO₅(49873-82-7)
• EPA Substance Registry System: C₁₄H₁₉NO₅(49873-82-7)

Safety Data

• Hazardous Substances Data: 49873-82-7(Hazardous Substances Data)

Upstream product

• 3426-71-9 Benzyl N-hydroxycarbamate 
• 28659-87-2 (S)-2-bromo-4-methylpentanoic acid 
• 61-90-5 L-leucine 

Downstream Products

• 795300-59-3 C₁₉H₃₀N₂O₄ 
• 795300-51-5 C₁₅H₁₉N₃O₄ 
• 795300-55-9 (R)-5-Isobutyl-3-oxo-isoxazolidine-2-carboxylic acid benzyl ester 

Relevant articles and documents

α-Aminoxy Oligopeptides: Synthesis, Secondary Structure, and Cytotoxicity of a New Class of Anticancer Foldamers

α-Aminoxy peptides are peptidomimetic foldamers with high proteolytic and conformational stability. To gain an improved synthetic access to α-aminoxy oligopeptides we used a straightforward combination of solution- and solid-phase-supported methods and obtained oligomers that showed a remarkable anticancer activity against a panel of cancer cell lines. We solved the first X-ray crystal structure of an α-aminoxy peptide with multiple turns around the helical axis. The crystal structure revealed a right-handed 28-helical conformation with precisely two residues per turn and a helical pitch of 5.8 ?. By 2D ROESY experiments, molecular dynamics simulations, and CD spectroscopy we were able to identify the 28-helix as the predominant conformation in organic solvents. In aqueous solution, the α-aminoxy peptides exist in the 28-helical conformation at acidic pH, but exhibit remarkable changes in the secondary structure with increasing pH. The most cytotoxic α-aminoxy peptides have an increased propensity to take up a 28-helical conformation in the presence of a model membrane. This indicates a correlation between the 28-helical conformation and the membranolytic activity observed in mode of action studies, thereby providing novel insights in the folding properties and the biological activity of α-aminoxy peptides.

Synthesis and characterization of chiral N-O turns induced by α-aminoxy acids

Chiral α-aminoxy acids of various side chains were synthesized with high optical purity starting from chiral α-amino acids. The conformations of diamides 13a-e, 15, and 16 were probed by using NMR, FT-IR, and CD spectroscopic methods as well as X-ray crystallography. The right-handed turns with eight-membered-ring intramolecular hydrogen bonds between adjacent residues (called the N-O turns) were found to be preferred for D-aminoxy acid residues, and they were independent of the side chains. The rigid chiral N-O turns should have great potential in molecular design.