Biaryl Peptides from 4‐Iodophenylalanine by Solid‐Phase Borylation and Suzuki–Miyaura Cross‐Coupling

Afonso, Ana; Rosés, Cristina; Planas, Marta; Feliu, Lidia

doi:10.1002/ejoc.200901350

Cited by 21 publications

(22 citation statements)

References 27 publications

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“…This process is the first example to construct the C−C bond containing‐biaryl skeleton on amino acid‐based isoxazole moiety. Later, Feliu and co‐workers extended this strategy to peptide modification via SM coupling. Hackenberger and Böhrsch described a simple and an efficient catalytic system under aqueous reaction conditions for the synthesis of the biaryl moiety via SM cross‐coupling with the aid of a pyrimidine ligand.…”

Section: Peptide Modificationmentioning

confidence: 99%

Development of New Synthetic Strategies, Tactics and their Applications

Kotha

Meshram

2019

The Chemical Record

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This account covers our work related to the development of various synthetic methodologies since 1994. We summarized our strategies and their application to design various functional molecules. In this regard, we also report the utility of our methodologies in others research work. These methods we report here are simple and efficient for the synthesis of a wide variety of intricate molecules such as heterocycles, polycycles, unusual α‐amino acids, star‐shaped molecules, and modified peptides. For this purpose, we used various transition metal‐based reagents and catalysts. Various popular reactions such as metathesis, Suzuki coupling, [2+2+2] cyclotrimerization were used to assemble these targets. Moreover, rongalite has been used to expand the Diels‐Alder chemistry.

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Section: Peptide Modificationmentioning

confidence: 99%

Development of New Synthetic Strategies, Tactics and their Applications

Kotha

Meshram

2019

The Chemical Record

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“…Interestingly, Afonso et al disclosed for the first time the preparation of biaryl-containing peptides from 4-iodophenylalanine by sequential solid-phase borylation and Suzuki-Miyaura conversion [158]. Their approach relied on the introduction of the arylboron group by Miyaura borylation on Rink Amide resin.…”

Section: Solid-phase Derivatizations Of Peptide Substratesmentioning

confidence: 99%

“…Afonso et al extended their work on cross-couplings of borylated peptides on solid support [158] through the cyclization of a linear peptide, for example, 111, containing both the boronate and the halogenated aromatic amino acid [120]. Different ring sizes were obtained by varying both the length of the peptide sequence (three to eight residues) and the position of the halogen atom on the Figure 16A.…”

Section: Formation Of Biaryl-bridges In Peptidic Natural Products Andmentioning

confidence: 99%

“…However, in case of transformations on highly complex proteins, containing multiple complexation sites, superstoichiometrical quantities (often palladium >50 eq, boronic acid >500 eq) are required. Since the allowed palladium level thresholds in active pharmaceutical ingredients are Afonso et al extended their work on cross-couplings of borylated peptides on solid support [158] through the cyclization of a linear peptide, for example, 111, containing both the boronate and the halogenated aromatic amino acid [120]. Different ring sizes were obtained by varying both the length of the peptide sequence (three to eight residues) and the position of the halogen atom on the N-terminal amino acid (p-I-Phe, m-I-Tyr and 3-Br-His).…”

Section: Protein Derivatizationmentioning

confidence: 99%

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The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

et al. 2017

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Abstract:The (site-selective) derivatization of amino acids and peptides represents an attractive field with potential applications in the establishment of structure-activity relationships and labeling of bioactive compounds. In this respect, bioorthogonal cross-coupling reactions provide valuable means for ready access to peptide analogues with diversified structure and function. Due to the complex and chiral nature of peptides, mild reaction conditions are preferred; hence, a suitable cross-coupling reaction is required for the chemical modification of these challenging substrates. The Suzuki reaction, involving organoboron species, is appropriate given the stability and environmentally benign nature of these reactants and their amenability to be applied in (partial) aqueous reaction conditions, an expected requirement upon the derivatization of peptides. Concerning the halogenated reaction partner, residues bearing halogen moieties can either be introduced directly as halogenated amino acids during solid-phase peptide synthesis (SPPS) or genetically encoded into larger proteins. A reversed approach building in boron in the peptidic backbone is also possible. Furthermore, based on this complementarity, cyclic peptides can be prepared by halogenation, and borylation of two amino acid side chains present within the same peptidic substrate. Here, the Suzuki-Miyaura reaction is a tool to induce the desired cyclization. In this review, we discuss diverse amino acid and peptide-based applications explored by means of this extremely versatile cross-coupling reaction. With the advent of peptide-based drugs, versatile bioorthogonal conversions on these substrates have become highly valuable.

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“…Among them, complex cyclic peptides with a biaryl bridge motif show biologically relevant activities, such as antimicrobial, proteasome inhibition or cytotoxic . Over recent years, the use of catalyzed cross‐coupling reactions has been extended to solid‐phase peptide synthesis (SPPS) . In particular, the Suzuki–Miyaura reaction allows C–C bond construction in mild conditions and in a safe environment, thereby allowing access to drug‐like molecules that can mimic the natural biaryl bond used as a conformational constraint and a site for recognition of protein surfaces.…”

Section: Introductionmentioning

confidence: 99%

Bike peptides: a ride through the membrane

García-Pindado

Royo

Teixidó

et al. 2017

Journal of Peptide Science

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Several natural peptides have a biaryl or biaryl ether motif in their biologically active structures. A model bicyclic pentapeptide containing a biaryl bridge has been synthesized by solid-phase peptide synthesis combining on-resin Suzuki and Miyaura cross-coupling reactions. Its biological properties in terms of permeability, stability and cytotoxicity have been studied, demonstrating the positive contribution of the biaryl bridge, excellent membrane penetration and serum stability Copyright © 2017 European Peptide Society and John Wiley & Sons, Ltd.

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Biaryl Peptides from 4‐Iodophenylalanine by Solid‐Phase Borylation and Suzuki–Miyaura Cross‐Coupling

Cited by 21 publications

References 27 publications

Development of New Synthetic Strategies, Tactics and their Applications

Development of New Synthetic Strategies, Tactics and their Applications

The Suzuki–Miyaura Cross-Coupling as a Versatile Tool for Peptide Diversification and Cyclization

Bike peptides: a ride through the membrane

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