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

  • Org Lett. 2015 Sep 4;17(17):4264-7. doi: 10.1021/acs.orglett.5b02057.
Yohei Okada  1 ,  Hiroki Wakamatsu  2 ,  Masae Sugai  2 ,  Esko I Kauppinen  1  3 ,  Kazuhiro Chiba  2
Affiliations
  • 1. Department of Chemical Engineering, Tokyo University of Agriculture and Technology , 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
  • 2. Department of Applied Biological Chemistry, Tokyo University of Agriculture and Technology , 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
  • 3. Department of Applied Physics, Aalto University School of Science , Puumiehenkuja 2, 00076 Aalto, Finland.
PMID: 26274781 DOI: 10.1021/acs.orglett.5b02057
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.

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