Side-Chain Modification of Peptides Using a Phosphoranylidene Amino Acid

Masri, Enaam; Ahsanullah,; Accorsi, Matteo; Rademann, Jörg

doi:10.1021/acs.orglett.0c00713

Cited by 10 publications

(10 citation statements)

References 47 publications

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“…for the incorporation of phosphorane moiety as side chain of peptides (Scheme 25). 60 Scheme 25. Synthesis of peptides containing phosphorane side chain and their ligation reactions 60 The synthetic plan involved conversion of N-Fmoc-protected Laspartic acid into the unnatural amino acid 89 carrying a triarylphosphonium salt in its side chain.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…Model peptides 90 were subsequently employed in side-chain variations using Wittig reactions to provide peptides carrying E-configured a,ß-unsaturated ketones 91 and applying 1,3-dipolar cycloaddition reactions to form peptides with 1,5disubstituted 1,2,3-triazole residues 92. 60 The methodology enables the systematic variation and replacement of native amino acid residues by alternative fragments and will allow the optimization of peptides for application in medicinal chemistry and chemical biology. Moreover, the peptides bearing vinyl ketones as Michael acceptors in the side chain might serve as electrophilic probe for subsequent reactions, including addition of bis-nucleophiles leading to diverse heterocycles.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…An interesting application of this chemistry is the cyclization of peptides through side chain triazole ligation. 61 3. 63 Scheme 26.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

“…This chemistry was extended by the Rademann group to the incorporation of the phosphorane moiety into the side chain of peptides (Scheme 25). 60 Scheme 25 Synthesis of peptides containing a phosphorane side chain and their ligation reactions 60 The synthetic plan involved conversion of N-Fmoc-protected L-aspartic acid into the unnatural amino acid 89 carrying a triarylphosphonium salt in its side chain. The preparation of phosphoranylidene amino acid 89 was achieved by C-acylation of phosphoranylideneacetate 88 with aspartic acid.…”

Section: Short Review Synthesismentioning

confidence: 99%

“…This chemistry was extended by the Rademann group to the incorporation of the phosphorane moiety into the side chain of peptides (Scheme 25 ). 60…”

Section: Ylides As Substrates For C -Acylationmentioning

confidence: 99%

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Integration of C-Acylation in the Solid-Phase Synthesis of Peptides and Peptidomimetics Employing Meldrum’s Acid, Phosphorus, and Sulfur Ylides

et al. 2021

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Modification of native peptides to peptidomimetics is an important goal in medicinal chemistry and requires in many cases the integration of C-acylation steps involving amino acids with peptide synthesis. Many classical C-acylation protocols involving Claisen condensations or the use of ylides are not compatible with peptide synthesis, mostly due to the requirement of strong bases leading to epimerization or deprotection of peptides. Meldrum’s acid as well as several specific phosphorus and sulfur ylides, however, are acidic enough to provide reactive C-nucleophiles at mildly basic conditions tolerated during peptide synthesis. This review provides an overview of peptide-compatible C-acylations of Meldrum´s acid, phosphorus and sulfur ylides and their application in the medicinal chemistry of peptides.

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Section: Accepted Manuscriptmentioning

confidence: 99%

Section: Accepted Manuscriptmentioning

confidence: 99%

“…An interesting application of this chemistry is the cyclization of peptides through side chain triazole ligation. 61 3. 63 Scheme 26.…”

Section: Accepted Manuscriptmentioning

confidence: 99%

Section: Short Review Synthesismentioning

confidence: 99%

“…This chemistry was extended by the Rademann group to the incorporation of the phosphorane moiety into the side chain of peptides (Scheme 25 ). 60…”

Section: Ylides As Substrates For C -Acylationmentioning

confidence: 99%

See 3 more Smart Citations

Integration of C-Acylation in the Solid-Phase Synthesis of Peptides and Peptidomimetics Employing Meldrum’s Acid, Phosphorus, and Sulfur Ylides

et al. 2021

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Rational Design of Peptides and Protein Molecules in Drug Discovery

Padhy,

Biswas,

Nayak

et al. 2024

Computational Methods for Rational Drug Design

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Advances in screening, synthesis, modification, and biomedical applications of peptides and peptide aptamers

Liu,

Lu,

Chen

et al. 2023

BioFactors

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Peptides and peptide aptamers have emerged as promising molecules for a wide range of biomedical applications due to their unique properties and versatile functionalities. The screening strategies for identifying peptides and peptide aptamers with desired properties are discussed, including high‐throughput screening, display screening technology, and in silico design approaches. The synthesis methods for the efficient production of peptides and peptide aptamers, such as solid‐phase peptide synthesis and biosynthesis technology, are described, along with their advantages and limitations. Moreover, various modification techniques are explored to enhance the stability, specificity, and pharmacokinetic properties of peptides and peptide aptamers. This includes chemical modifications, enzymatic modifications, biomodifications, genetic engineering modifications, and physical modifications. Furthermore, the review highlights the diverse biomedical applications of peptides and peptide aptamers, including targeted drug delivery, diagnostics, and therapeutic. This review provides valuable insights into the advancements in screening, synthesis, modification, and biomedical applications of peptides and peptide aptamers. A comprehensive understanding of these aspects will aid researchers in the development of novel peptide‐based therapeutics and diagnostic tools for various biomedical challenges.

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Side-Chain Modification of Peptides Using a Phosphoranylidene Amino Acid

Cited by 10 publications

References 47 publications

Integration of C-Acylation in the Solid-Phase Synthesis of Peptides and Peptidomimetics Employing Meldrum’s Acid, Phosphorus, and Sulfur Ylides

Integration of C-Acylation in the Solid-Phase Synthesis of Peptides and Peptidomimetics Employing Meldrum’s Acid, Phosphorus, and Sulfur Ylides

Rational Design of Peptides and Protein Molecules in Drug Discovery

Advances in screening, synthesis, modification, and biomedical applications of peptides and peptide aptamers

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