Hydrophobic tag-assisted liquid-phase peptide synthesis technique and disulfide bond formation have been well-combined, leading to the efficient and practical preparation of a growth hormone-inhibiting peptide somatostatin. Intramolecular disulfide bond formation has successfully been carried out even under relatively high concentrations, enabling the effective peptide modifications in preparative scale.
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| http://dx.doi.org/10.1016/j.bmcl.2011.06.004 | DOI Listing |
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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.
Fluorous-tag assisted synthesis of a glycosaminoglycan mimetic tetrasaccharide as a high-affinity FGF-2 and midkine ligand.
Bioorg Med Chem
March 2018
Glycosystems Laboratory, Instituto de Investigaciones Químicas (IIQ), cicCartuja, CSIC and Universidad de Sevilla, Americo Vespucio, 49, 41092 Sevilla, Spain. Electronic address:
Here, we present the preparation of a sulfated, fully protected tetrasaccharide derivative following the glycosaminoglycan (GAG)-related sequence GlcNAc-β(1 → 4)-Glc-β(1 → 3). The tetramer was efficiently assembled via an iterative glycosylation strategy using monosaccharide building blocks. A fluorous tag was attached at position 6 of the reducing end unit enabling the purification of reaction intermediates by simple fluorous solid phase extraction.
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 PDFTag-assisted liquid-phase peptide synthesis using hydrophobic benzyl alcohols as supports.
J Org Chem
January 2013
Department of Applied Biological Science, Tokyo University of Agriculture and Technology, Fuchu, Tokyo 183-8509, Japan.
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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