Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2022; 18(09): 1041
DOI: 10.1055/s-0041-1738561
DOI: 10.1055/s-0041-1738561
Innovative Drug Discovery and Development
Isonitrile Couplings Enable a Modular Synthesis of Cyclosporin A
Wu X,
Stockdill JL,
Wang P,
Danishefsky SJ.
*
Sloan-Kettering Institute for Cancer Research and Columbia University, New York, USA
Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions.
J. Am. Chem. Soc. 2010;
132: 4098-4100
DOI: 10.1021/ja100517v.
Total Synthesis of Cyclosporine: Access to N-Methylated Peptides via Isonitrile Coupling Reactions.
J. Am. Chem. Soc. 2010;
132: 4098-4100
DOI: 10.1021/ja100517v.
Significance
Cyclosporin A is a reversible inhibitor of cytokines in T helper cells. Clinically, it is used as an immunosuppressant, allowing for otherwise non-sustainable organ transplants. Additionally, it is used to treat rheumatoid arthritis and Crohn’s disease.
#
Comment
Novel isonitrile couplings were used to form peptide bonds. A nucleophilic addition yielded a thio-formimidate mixed anhydride, which underwent a 1,3-O→N acyl shift to generate an N-thioformyl amide.
#
#
Publication History
Article published online:
18 August 2022
© 2022. Thieme. All rights reserved
Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany