Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic Flash Switching in a Micro-flow Reactor.

Rapid and Mild Synthesis of Amino Acid N-Carboxy Anhydrides Using Basic-to-Acidic Flash Switching in a Micro-flow Reactor. Angew Chem Int Ed Engl. 2018 Jul 12;: Authors: Otake Y, Nakamura H, Fuse S Abstract Polymerization of N-carboxy anhydrides (NCAs) is the primary process used to prepare polypeptides. The synthesis of various pure NCAs is a 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. We used "basic-to-acidic flash switching" and subsequent "flash dilution" technology in a micro-flow reactor to demonstrate synthesis of NCAs that is both rapid (0.1 s) and mild (20 °C) and includes versions containing acid-labile functional groups. The basic-to-acidic flash switching enabled both an acceleration of the desired NCA formation and an avoidance of the undesired ring opening of NCAs. The flash dilution avoided the undesired decomposition of acid-labile functional groups. The developed process allowed us to synthesize various NCAs that cannot be readily synthesized using conventional batch methods. PMID: 29998576 [PubMed - as supplied by publisher]
Source: Angewandte Chemie - Category: Chemistry Authors: Tags: Angew Chem Int Ed Engl Source Type: research
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