Synthesis of Fluorescent Jasplakinolide Analogues for Live-Cell STED Microscopy of Actin.

ABSTRACT: The nanometer thickness of filaments and the dynamic behavior of actin-a protein playing a crucial role in cellular function and motility-make it attractive for observation with super-resolution optical microscopy. We developed the solution-phase synthesis of des-bromo-des-methyl-jasplakinolide-lysine, used as the "recognition unit" (ligand) for F-actin in living cells. The first amino acid-Fmoc-O-TIPS-β-tyrosine-was prepared in 78% yield (two steps in one pot). The new solution-phase synthesis involves 2-phenylisopropyl protection of the carboxyl group and does not require excesses of commercially unavailable amino acids. The overall yield of the target intermediate obtained in nine steps is about 8%. The 2-phenylisopropyl group can be cleaved from carboxyl with 2-3% (v/v) of TFA i

SUBMITTER: Belov VN 

PROVIDER: S-EPMC7281785 | biostudies-literature | 2020 Jun

REPOSITORIES: biostudies-literature