Acid-Triggered Colorimetric Hydrophobic Benzyl Alcohols for Soluble Tag-Assisted Liquid-Phase Synthesis.
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.
Department of Chemical Engineering, Tokyo University of Agriculture and Technology , 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.
Yohei
Y
Okada
Department of Applied Biological Chemistry, Tokyo University of Agriculture and Technology , 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
Hiroki
H
Wakamatsu
Department of Applied Biological Chemistry, Tokyo University of Agriculture and Technology , 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
Masae
M
Sugai
Department of Chemical Engineering, Tokyo University of Agriculture and Technology , 2-24-16 Naka-cho, Koganei, Tokyo 184-8588, Japan.|Department of Applied Physics, Aalto University School of Science , Puumiehenkuja 2, 00076 Aalto, Finland.
Esko I
EI
Kauppinen
Department of Applied Biological Chemistry, Tokyo University of Agriculture and Technology , 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
Kazuhiro
K
Chiba
D000438:Alcohols; D016229:Amyloid beta-Peptides / Q000737:chemistry; D001592:Benzyl Alcohols / Q000737:chemistry*; D060326:Chemistry Techniques, Synthetic; D003124:Colorimetry; D057927:Hydrophobic and Hydrophilic Interactions; D015394:Molecular Structure; D010446:Peptide Fragments / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D012995:Solubility; D012996:Solutions; D012997:Solvents / Q000737:chemistry
D000438:Alcohols; D016229:Amyloid beta-Peptides; D001592:Benzyl Alcohols; D010446:Peptide Fragments; D010455:Peptides; D012996:Solutions; D012997:Solvents; C474023:iAbeta5 peptide