Chemical synthesis of <i>Torenia</i> plant pollen tube attractant proteins by KAHA ligation

Kumarswamyreddy, Nandarapu; Reddy, Damodara N.; Robkis, D. Miklos; Kamiya, Nao; Tsukamoto, Ryoko; Kanaoka, Masahiro M.; Higashiyama, Tetsuya; Oishi, Shunsuke; Bode, Jeffrey W.

doi:10.1039/d2cb00039c

Cited by 3 publications

(1 citation statement)

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“…The KAHA ligation [67][68][69][70][71][72][73][74][75] operates under acidic conditions with water/organic solvent mixture ideal for solubilizing hydrophobic segments and resulting in more soluble peptide esters such as O-acyl isopeptide or depsi peptide as a primary ligation product. After rearrangement of the ligated product under the basic conditions, the resulting polypeptide contains a noncanonical amino acid residue homoserine (Hse), when using 5-oxaproline as a ligation handle on the N-terminus of the C-terminal peptide fragment.…”

Section: Synthesis Of Epf1 Protein By Kaha Ligationmentioning

confidence: 99%

Chemical synthesis of the EPF-family of plant cysteine-rich proteins and late-stage dye attachment by chemoselective amide-forming ligations

et al. 2022

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Section: Synthesis Of Epf1 Protein By Kaha Ligationmentioning

confidence: 99%

Chemical synthesis of the EPF-family of plant cysteine-rich proteins and late-stage dye attachment by chemoselective amide-forming ligations

et al. 2022

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Deciphering the Synthetic and Refolding Strategy of a Cysteine-Rich Domain in the Tumor Necrosis Factor Receptor (TNF-R) for Racemic Crystallography Analysis and d-Peptide Ligand Discovery

Lander,

Kong,

Jin

et al. 2023

ACS Bio Med Chem Au

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Many cell-surface receptors are promising targets for chemical synthesis because of their critical roles in disease development. This synthetic approach enables investigations by racemic protein crystallography and ligand discovery by mirrorimage methodologies. However, due to their complex nature, the chemical synthesis of a receptor can be a significant challenge. Here, we describe the chemical synthesis and folding of a central, cysteine-rich domain of the cell-surface receptor tumor necrosis factor 1 which is integral to binding of the cytokine TNF-α, namely, TNFR-1 CRD2. Racemic protein crystallography at 1.4 Å confirmed that the native binding conformation was preserved, and TNFR-1 CRD2 maintained its capacity to bind to TNF-α (K D ≈ 7 nM). Encouraged by this discovery, we carried out mirror-image phage display using the enantiomeric receptor mimic and identified a D-peptide ligand for TNFR-1 CRD2 (K D = 1 μM). This work demonstrated that cysteine-rich domains, including the central domains, can be chemically synthesized and used as mimics for investigations.

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Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds

Huang,

Yang,

Zhang

et al. 2024

Chinese Journal of Organic Chemistry

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Amide bond constructions are crucial in peptide synthesis and pharmaceutical chemistry research. The traditional methods of peptide synthesis require the use of excessive amounts reagents and solvents, posing a threat to the environment and human health. It is still the current research focus to develop environmentally friendly novel acylation reagents and efficient, green, and sustainable amide bond synthesis methods. From the green chemistry's principles, this paper is focused on the efficient formation of amide bonds in peptide, including the catalysis of elemental organic chemicals, some green solvents and reagents, and some physical strengthening methods, etc. The application of these methods and technologies was also discussed in peptide chemistry.

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Chemical synthesis of Torenia plant pollen tube attractant proteins by KAHA ligation

Abstract: The synthesis of secreted cysteine rich proteins (CRPs) is a long-standing challenge due to protein aggregation and premature formation of inter- and intramolecular disulfide bonds. Chemical synthesis provides reduced CRPs...

Cited by 3 publications

References 67 publications

Chemical synthesis of the EPF-family of plant cysteine-rich proteins and late-stage dye attachment by chemoselective amide-forming ligations

Chemical synthesis of the EPF-family of plant cysteine-rich proteins and late-stage dye attachment by chemoselective amide-forming ligations

Deciphering the Synthetic and Refolding Strategy of a Cysteine-Rich Domain in the Tumor Necrosis Factor Receptor (TNF-R) for Racemic Crystallography Analysis and d-Peptide Ligand Discovery

Recent Progress on Green Methods and Technologies for Efficient Formation of Amide Bonds

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