54680-72-7Relevant academic research and scientific papers
Studies on the mechanism of 1,2-dihydropyrazin-2-one ring formation from dipeptidyl chloromethyl ketone and its chemical properties: Immediate deamination during catalytic hydrogenation
Miyazaki, Anna,Fujisawa, Yutaka,Shiotani, Kimitaka,Fujita, Yoshio,Li, Tingyou,Tsuda, Yuko,Yokoi, Toshio,Bryant, Sharon D.,Lazarus, Lawrence H.,Okada, Yoshio
, p. 1152 - 1158 (2007/10/03)
1,2-Dihydropyrazin-2-one derivatives, which have two aminoalkyl groups at the positions 3 and 6, were found to be efficient tools for the construction of potent, selective and long-acting opioid mimetics. During the course of preparation, we found that the catalytic hydrogenation of 3,6- bis(benzyloxycarbonylaminomethyl)-5-methyl-1,2-dihydropyrazin-2-one to remove the benzyloxycarbonyl groups resulted in a side reaction. By MS and NMR studies and by preparation of additional 1,2-dihydropyrazin-2-one derivatives, the structure of the by-product was identified as 3-aminomethyl-5,6-dimethyl-1,2- dihydropyrazin-2-one. Preparation of additional compounds substituted with deuterium provided us with sufficient information to confirm the structure of the product and to support a cyclization mechanism in its formation.
Thermitase - A Thermostable Serine Protease. III. Synthesis of N-Acylated Peptide Methyl Ketones as Inhibitors Reversibly Bound to the Enzyme
Fittkau, Siegfried,Jahreis, Guenther
, p. 48 - 53 (2007/10/02)
Methyl ketone derivatives of dipeptides to pentapeptides are used as suitable tools in the investigation of the non-covalent binding for subsite mapping of the active site of the enzyme.The synthesis is mainly performed by fragment condensation of N-acylated peptides or amino acids with methyl ketone derivatives of amino acids.These are prepared from the Z-protected chloromethyl ketones by catalytic hydrogenation.For the coupling steps the Z-protection is preferred.The peptide methyl ketones used in kinetic studies were N-protected by the Z, acetyl, Boc or pyroglutamyl residue.
