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 |