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

作者:Okada Yohei; Wakamatsu Hiroki; Sugai Masae; Kauppinen Esko I; Chiba Kazuhiro*
来源:Organic Letters, 2015, 17(17): 4264-4267.
DOI:10.1021/acs.orglett.5b02057

摘要

Simple screening of acid-triggered reactions of methoxybenzyl alcohols led to the development of a novel colorirnetric 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 beta-sheet breaker peptide iA beta 5 (4) was achieved. The tagged peptides showed a vivid blue color under acidic conditions both on TLC plates and in solution, enabling quantitative assay.

  • 出版日期2015-9-4