Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki–Miyaura cross-coupling

Cerezo, Vanessa; Amblard, Muriel; Martinez, Jean; Verdié, Pascal; Planas, Marta; Feliu, Lidia

doi:10.1016/j.tet.2008.08.077

Cited by 26 publications

(51 citation statements)

References 20 publications

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“…It can be concluded that all the previous conventionally heated reaction can be easily performed by microwave heating. 24 Many microwave assisted solid phase reactions have been reported in recent years which may include cellular uptake, and cytotoxicity studies of cymantrene-peptide bioconjugates, 25 solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki-Miyaura cross-coupling, 26 synthesis of 1,2,4-oxadiazoles using polymer-bound triphenylphosphine reagent. 27 Recently solid-phase organic syntheses (SPOS) is evolving as a means to facilitate the manipulation of compound libraries via combinatorial chemistry.…”

Section: Introductionmentioning

confidence: 99%

Application of “Click” Chemistry in Solid Phase Synthesis of Alkyl Halides

Das¹,

Chanda²,

Rokhum

2015

ACSi

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A convenient and highly selective microwave assisted procedure for the conversion of allylic, benzylic and aliphatic alcohols to their corresponding halides using polymer-bound triphenylphosphine and iodine is presented. In case of symmetrical diols, mono-iodination product is obtained in very high yield. Additionally, highly regioselective behavior is observed in our procedure. Simplicity in operation, no column chromatography required for the purification of the products, recyclability of the reagents used, short reaction times and good to excellent yields are the advantages of our protocol. Most functional groups remain unaffected under our reaction condition.

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Section: Introductionmentioning

confidence: 99%

Application of “Click” Chemistry in Solid Phase Synthesis of Alkyl Halides

Das¹,

Chanda²,

Rokhum

2015

ACSi

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“…By switching the solvent system to DME/EtOH/H 2 O 9:9:2, in combination with the use of an aqueous solution of K 3 PO 4 , improved reaction efficiency was obtained, and gratifyingly, target arylated peptides 99 were accessed in acceptable isolated yields. In an extension of their work in solution phase [93], Cerezo reported the first solid-phase derivatization of 5-bromohistidine containing tripeptides (not shown) [159]. The 5-bromo-histidine residue was introduced as the N-terminal amino acid via SPPS on Rink MBHA resin and subjected to Suzuki-Miyaura reactions.…”

Section: Solid-phase Derivatizations Of Peptide Substratesmentioning

confidence: 99%

“…In view of the development of novel antimicrobial peptides, Ng-Choi et al incorporated 5-bromohistidine as a replacement of phenylalanine in undecapeptides at the 1-or 4-position (for example, 131, Figure 19B) [202]. Derivatization of these building blocks was previously reported on solid-phase [159] and afforded a small library of biaryl peptides, which were tested for their biological activity in comparison with the lead peptide H-FKLFKKILKFL-NH 2 . These arylhistidine-containing peptides displayed similar antibacterial and antifungal activity; however, a decreased hemolytic effect was observed.…”

Section: The Suzuki-miyaura Reaction As a Tool Towards Improved Biolomentioning

confidence: 99%

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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“…This methodology has allowed the synthesis of peptides bearing a histidine residue substituted at position 5 of the imidazole ring with a phenyl, a substituted phenyl, a pyridyl, or a thienyl ring, as well as with the benzene ring of a tyrosine residue. 3 A large number of N-aminodipeptide compounds have been obtained via a Mitsunobu protocol performed in solution or by solidphase synthesis. The oligomerisation of some of the products has been studied in solution or on solid support leading to the formation of 1:1[a:a ÀN-amino]mers.…”

Section: Solid-phase Synthesismentioning

confidence: 99%

Combinatorial Chemistry Online

Terrett

2008

Combinatorial Chemistry - an Online Journal

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Solid-phase synthesis of 5-arylhistidines via a microwave-assisted Suzuki–Miyaura cross-coupling

Cited by 26 publications

References 20 publications

Application of “Click” Chemistry in Solid Phase Synthesis of Alkyl Halides

Application of “Click” Chemistry in Solid Phase Synthesis of Alkyl Halides

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

Combinatorial Chemistry Online

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