Synlett 2020; 31(16): 1537-1542
DOI: 10.1055/s-0040-1707165
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© Georg Thieme Verlag Stuttgart · New York

Peptide Cyclization at High Concentration

Rachel D. Wills
,
Victor T. Adebomi
,
Monika Raj
Department of Chemistry and Biochemistry, Auburn University Auburn, AL 36830, USA   Email: [email protected]
› Author Affiliations
This research was supported by the National Science Foundation (Grant No. CHE-1752654) granted to M.R.
Further Information

Publication History

Received: 11 May 2020

Accepted after revision: 21 May 2020

Publication Date:
08 July 2020 (online)


Abstract

The emergence of cyclic peptides as pharmaceuticals has led to an eruption of new methodologies for macrocyclization. However, the cyclization of peptides at high concentrations presents a challenge due to the production of side products like dimers and oligomers. This factor is more pronounced with the cyclization of peptides composed of fewer than seven amino acids, thus has created a need for a new synthetic strategy. Herein, we will elucidate a new chemoselective method termed ‘CyClick’ that works in an exclusively intramolecular fashion preventing the formation of commonly occurring side products such as dimers and oligomers, even at relatively high concentration.

1 Introduction

2 Known Methodologies

3 Novel CyClick Chemistry

4 Conclusion and Outlook

 
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