88265-31-0Relevant academic research and scientific papers
Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides: Basic-to-Acidic Flash Switching in a Microflow Reactor
Otake, Yuma,Nakamura, Hiroyuki,Fuse, Shinichiro
supporting information, p. 11389 - 11393 (2018/08/28)
Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is key to the efficient synthesis of polypeptides. The only practical method that can be used to synthesize NCAs requires harsh acidic conditions that make acid-labile substrates unusable and results in an undesired ring opening of NCAs. Basic-to-acidic flash switching and subsequent flash dilution technology in a microflow reactor was used to demonstrate the synthesis of NCAs. It is both rapid (0.1 s) and mild (20 °C) and includes substrates containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and avoided the undesired ring opening of NCAs. The flash dilution precluded the undesired decomposition of acid-labile functional groups. The developed process allowed the synthesis of various NCAs which cannot be readily synthesized using conventional batch methods.
Solid-phase, solution, and segment condensation peptide syntheses incorporating chromium carbene complex-derived nonproteinogenic ("unnatural") amino acid fragments
Pulley, Shon R.,Hegedus, Louis S.
, p. 9037 - 9047 (2007/10/02)
Photolysis of optically active chromium aminocarbene complexes in the presence of tripeptide methyl esters gave protected tetrapeptide methyl esters in good yield and with good diastereoselectivity. Photolysis of these same carbene complexes in the presen
