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A trimethyllysine-containing trityl tag for solubilizing hydrophobic peptides
Shun Masuda1, Shugo Tsuda1, Taku Yoshiya1
1Peptide Institute, Inc., Ibaraki, Osaka 567-0085, Japan. t.yoshiya@peptide.co.jp.
Organic & Biomolecular Chemistry
|November 30, 2019
Summary
Preparing hydrophobic peptides is challenging due to low water solubility. Researchers compared several peptidic trityl tags, finding that Nε-tri-Me-Lys tags offer superior solubilization for hydrophobic peptides.
Area of Science:
- Biochemistry
- Protein Chemistry
- Biotechnology
Background:
- Hydrophobic membrane peptides and proteins present challenges in preparation due to poor water solubility.
- Temporal introduction of solubilizing tags is a viable strategy to improve peptide and protein solubility.
Purpose of the Study:
- To comparatively evaluate the solubilizing abilities of various peptidic trityl tags.
- To identify the most effective tag for enhancing the solubility of hydrophobic peptides.
Main Methods:
- Synthesis and application of several peptidic trityl tags, including those with Lys, Arg, Glu, Asn, Nε-tri-Me-Lys, and Cys-sulfonate.
- Testing the efficacy of these tags on two hydrophobic model peptides.
Main Results:
- The Nε-tri-Me-Lys containing tag demonstrated superior solubilizing ability compared to other evaluated tags.
- The study provides a comparative analysis of different tag compositions for hydrophobic peptide solubilization.
Conclusions:
- Peptidic trityl tags are effective for improving the solubility of hydrophobic peptides.
- Nε-tri-Me-Lys based tags represent a promising approach for overcoming solubility limitations in peptide preparation.

