Acid-Triggered Colorimetric Hydrophobic Benzyl Alcohols for Soluble Tag-Assisted Liquid-Phase Synthesis.

Abstract

Simple screening of acid-triggered reactions of methoxybenzyl alcohols led to the development of a novel colorimetric hydrophobic benzyl alcohol (HBA) tag. HBA tag-3 (14) retained high solubility in less polar solvents and excellent precipitation properties in polar solvents. Our routine procedure for tag-assisted liquid phase peptide synthesis was applied using HBA tag-3 (14), and an effective synthesis of β-sheet breaker peptide iAβ5 (4) was achieved. The tagged peptides showed a vivid blue color under acidic conditions both on TLC plates and in solution, enabling quantitative assay.