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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.
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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.
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Publication History
Article published online:
18 August 2022
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