Macrocyclization of Unprotected Peptide Isocyanates.
| Publication Type | Academic Article |
| Authors | Vinogradov A, Choo Z, Totaro K, Pentelute B |
| Journal | Org Lett |
| Volume | 18 |
| Issue | 6 |
| Pagination | 1226-9 |
| Date Published | 03/07/2016 |
| ISSN | 1523-7052 |
| Keywords | Isocyanates, Peptides |
| Abstract | A chemistry for the facile two-component macrocyclization of unprotected peptide isocyanates is described. Starting from peptides containing two glutamic acid γ-hydrazide residues, isocyanates can be readily accessed and cyclized with hydrazides of dicarboxylic acids. The choice of a nucleophilic linker allows for the facile modulation of biochemical properties of a macrocyclic peptide. Four cyclic NYAD-1 analogues were synthesized using the described method and displayed a range of biological activities. |
| DOI | 10.1021/acs.orglett.5b03626 |
| PubMed ID | 26948900 |