A soluble tag-assisted liquid-phase peptide synthesis was successfully established based on simple hydrophobic benzyl alcohols, which can be easily prepared from naturally abundant materials. Excellent precipitation yields can be obtained at each step, combining the best properties of solid-phase and liquid-phase techniques. This approach can also be applied efficiently to fragment couplings, allowing chemical synthesis of several bioactive peptides.
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Article Synopsis
- Tag-assisted liquid-phase peptide synthesis (LPPS) is crucial for pharmaceutical discovery, and incorporating simple silyl groups as hydrophobic tags enhances peptide synthesis.
- New super silyl-based groups (tris(trihexylsilyl)silyl and propargyl super silyl) were developed to improve solubility and reactivity during LPPS, allowing for efficient peptide synthesis.
- These groups are compatible with various chemistry methods (Cbz, Fmoc, and Boc) and have proven effective in synthesizing the peptide Nelipepimut-S with fewer preparation steps than previous methods.
Biphasic electrochemical peptide synthesis.
Chem Sci
October 2021
Department of Applied Biological Science, Tokyo University of Agriculture and Technology 3-5-8- Saiwai-cho Fuchu Tokyo 183-8509 Japan
The large amount of waste derived from coupling reagents is a serious drawback of peptide synthesis from a green chemistry viewpoint. To overcome this issue, we report an electrochemical peptide synthesis in a biphasic system. Anodic oxidation of triphenylphosphine (PhP) generates a phosphine radical cation, which serves as the coupling reagent to activate carboxylic acids, and produces triphenylphosphine oxide (PhP[double bond, length as m-dash]O) as a stoichiometric byproduct.
View Article and Find Full Text PDFAcid-Triggered Colorimetric Hydrophobic Benzyl Alcohols for Soluble Tag-Assisted Liquid-Phase Synthesis.
Org Lett
September 2015
Department of Applied Biological Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
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.
View Article and Find Full Text PDFHydrophobic benzyl amines as supports for liquid-phase C-terminal amidated peptide synthesis: application to the preparation of ABT-510.
J Pept Sci
September 2015
Department of Applied Biological Chemistry, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo, 183-8509, Japan.
C-terminal amidation is one of the most common modification of peptides and frequently found in bioactive peptides. However, the C-terminal modification must be creative, because current chemical synthetic techniques of peptides are dominated by the use of C-terminal protecting supports. Therefore, it must be carried out after the removal of such supports, complicating reaction work-up and product isolation.
View Article and Find Full Text PDFSoluble tag-assisted peptide head-to-tail cyclization: total synthesis of mahafacyclin B.
Org Lett
March 2013
Department of Applied Biological Science, Tokyo University of Agriculture and Technology, 3-5-8 Saiwai-cho, Fuchu, Tokyo 183-8509, Japan.
A soluble tag-assisted liquid-phase method was successfully applied to peptide head-to-tail cyclization, leading to the total synthesis of antimalarial cyclic heptapeptide, mahafacyclin B (1). The cyclization was carried out in the liquid phase with the tag remaining, which allowed rapid reaction workup and product isolation.
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