A fascinating journey into history: Exploration of the world of isonitriles en route to complex amides Journal Article
| Authors: | Wilson, R. M.; Stockdill, J. L.; Wu, X.; Li, X.; Vadola, P. A.; Park, P. K.; Wang, P.; Danishefsky, S. J. |
| Article Title: | A fascinating journey into history: Exploration of the world of isonitriles en route to complex amides |
| Abstract: | We describe herein our recent explorations in the field of isonitrile chemistry. An array of broadly useful coupling methodologies has been developed for the formation of peptidyl and glycopeptidyl amide bonds. We further describe the application of these methods to the syntheses of complex systems, including the cyclic peptide cyclosporine A, constrained peptide systems, and heterocycles. New take on an old classic: Recent explorations in the field of isonitrile chemistry led to the development of an array of broadly useful coupling methods for the formation of peptidyl and glycopeptidyl amide bonds. The methods were applied to the syntheses of complex systems, including the cyclic peptide cyclosporine A, constrained peptide systems, and heterocycles (see scheme; FCMA=formimidate carboxylate mixed anhydride). Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. |
| Keywords: | peptide; chemistry; glycosylation; peptides; heterocyclic compounds; heterocyclic compound; cyclosporin; cyclosporine; nitriles; synthesis; cyclic peptides; glycopeptide; glycopeptides; isonitriles; nitrile; stereoisomerism; carboxylic acids; amide bond; amides; amide; carboxylic acid; en-route; thiol derivative; heterocycles; multicomponent coupling; carboxylation; sulfhydryl compounds; coupling methods; cyclosporine a; multi-component coupling; peptide system |
| Journal Title: | Angewandte Chemie - International Edition |
| Volume: | 51 |
| Issue: | 12 |
| ISSN: | 1433-7851 |
| Publisher: | Wiley Blackwell |
| Date Published: | 2012-03-19 |
| Start Page: | 2834 |
| End Page: | 2848 |
| Language: | English |
| DOI: | 10.1002/anie.201106628 |
| PROVIDER: | scopus |
| PUBMED: | 22368033 |
| PMCID: | PMC3409437 |
| DOI/URL: | |
| Notes: | --- - "Export Date: 2 April 2012" - "CODEN: ACIEF" - "Source: Scopus" |
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