Submitted by api_import on December 20, 2019 - 3:16pm
| Title | Macrocyclization of Unprotected Peptide Isocyanates. |
| Publication Type | Journal Article |
| Year of Publication | 2016 |
| Authors | Vinogradov AA, Choo Z-N, Totaro KA, Pentelute BL |
| Journal | Org Lett |
| Volume | 18 |
| Issue | 6 |
| Pagination | 1226-9 |
| Date Published | 2016 Mar 18 |
| ISSN | 1523-7052 |
| Keywords | Amino Acid Sequence, Catalysis, Cyclization, Dicarboxylic Acids, Glutamates, Isocyanates, Molecular Structure, Peptides, Peptides, Cyclic |
| 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 |
| Alternate Journal | Org. Lett. |
| PubMed ID | 26948900 |