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Sustainable synthesis of N -methylated peptides in a continuous-flow fixed bed reactor

Sustainable synthesis of N -methylated peptides in a continuous-flow fixed bed reactor Abstract A rapid, simplified and highly efficient continuous-flow solid-phase peptide synthesis technology is reported for the direct synthesis of mono and multiple N-methylated cyclic alanine and valine peptides. Through an optimization study, we find that only 1.5 equivalents of the amino acids are sufficient for the couplings to maintain excellent conversions. Importantly, the technology is outstandingly sustainable, since three chemical steps are cancelled from the procedure and low amount of solvent is used, compared to traditional technologies. Furthermore, it is also applicable to the coupling of challenging amino acids, since pentavalines were constructed with high yield. The technology was successfully upscaled and peptide cyclization was carried out too. ᅟ http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Journal of Flow Chemistry Springer Journals

Sustainable synthesis of N -methylated peptides in a continuous-flow fixed bed reactor

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Publisher
Springer Journals
Copyright
2018 Akadémiai Kiadó
ISSN
2062-249X
eISSN
2063-0212
DOI
10.1007/s41981-018-0002-9
Publisher site
See Article on Publisher Site

Abstract

Abstract A rapid, simplified and highly efficient continuous-flow solid-phase peptide synthesis technology is reported for the direct synthesis of mono and multiple N-methylated cyclic alanine and valine peptides. Through an optimization study, we find that only 1.5 equivalents of the amino acids are sufficient for the couplings to maintain excellent conversions. Importantly, the technology is outstandingly sustainable, since three chemical steps are cancelled from the procedure and low amount of solvent is used, compared to traditional technologies. Furthermore, it is also applicable to the coupling of challenging amino acids, since pentavalines were constructed with high yield. The technology was successfully upscaled and peptide cyclization was carried out too. ᅟ

Journal

Journal of Flow ChemistrySpringer Journals

Published: Mar 1, 2018

References