Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage

Ng-Choi, Iteng; Oliveras, Àngel; Planas, Marta; Feliu, Lidia

doi:10.1016/j.tet.2019.03.014

Cited by 11 publications

(8 citation statements)

References 48 publications

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“…The diversity of synthetic peptides entering clinical trials has increased over the last 13 years, stimulating advances in Fmoc SPPS technologies in response to the growing demand for medicinal chemistry and pharmacology (Behrendt et al, 2016). Several groups have synthesized linear (Tran et al, 2008;Magliani et al, 2011;Konno et al, 2015;Cools et al, 2017;Park et al, 2018) and cyclic peptides (Mosca et al, 2000;Schaaper et al, 2001;Konno et al, 2015;Ng-Choi et al, 2019) using Fmoc SPPS.…”

Section: Chemical Synthesismentioning

confidence: 99%

Antifungal Peptides as Therapeutic Agents

Ullivarri

Arbulu

García-Gutiérrez

et al. 2020

Front. Cell. Infect. Microbiol.

174

132

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Fungi have been used since ancient times in food and beverage-making processes and, more recently, have been harnessed for the production of antibiotics and in processes of relevance to the bioeconomy. Moreover, they are starting to gain attention as a key component of the human microbiome. However, fungi are also responsible for human infections. The incidence of community-acquired and nosocomial fungal infections has increased considerably in recent decades. Antibiotic resistance development, the increasing number of immunodeficiency-and/or immunosuppression-related diseases and limited therapeutic options available are triggering the search for novel alternatives. These new antifungals should be less toxic for the host, with targeted or broader antimicrobial spectra (for diseases of known and unknown etiology, respectively) and modes of actions that limit the potential for the emergence of resistance among pathogenic fungi. Given these criteria, antimicrobial peptides with antifungal properties, i.e., antifungal peptides (AFPs), have emerged as powerful candidates due to their efficacy and high selectivity. In this review, we provide an overview of the bioactivity and classification of AFPs (natural and synthetic) as well as their mode of action and advantages over current antifungal drugs. Additionally, natural, heterologous and synthetic production of AFPs with a view to greater levels of exploitation is discussed. Finally, we evaluate the current and potential applications of these peptides, along with the future challenges relating to antifungal treatments.

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Section: Chemical Synthesismentioning

confidence: 99%

Antifungal Peptides as Therapeutic Agents

Ullivarri

Arbulu

García-Gutiérrez

et al. 2020

Front. Cell. Infect. Microbiol.

174

132

View full text Add to dashboard Cite

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“…In fact, a scarce number of research groups has addressed the solid-phase synthesis of cyclic peptides incorporating a Phe-Phe, Phe-Tyr, Tyr-Tyr, Trp-Phe or a Trp-Tyr linkage (Afonso et al 2011(Afonso et al , 2012Meyer et al 2012;Mendive-Tapia et al 2015;García-Pindado et al 2017;Ng-Choi et al 2019a). In this context, we have recently developed a solid-phase strategy for the synthesis of biaryl cyclic peptides containing a His-Tyr bond (Ng-Choi et al 2019b). A linear peptidyl resin incorporating a 5-bromohistidine and a 3-boronotyrosine was used as precursor and the cyclization was performed through a microwave-assisted Suzuki-Miyaura cross-coupling.…”

Section: Introductionmentioning

confidence: 99%

Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a Histidine-Phenylalanine Linkage

Ng-Choi

Oliveras

Feliu

et al. 2019

Int J Pept Res Ther

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The feasibility of the solid-phase intramolecular 4(5)-arylation of a histidine residue to obtain biaryl cyclic peptides bearing a His-Phe linkage was established. The synthetic strategy involved the preparation of a linear peptidyl resin incorporating a 5-bromohistidine and a 4-boronophenylalanine, and its cyclization through the formation of the biaryl bond between the imidazole of histidine and the phenyl group of phenylalanine via a microwave-assisted Suzuki-Miyaura cross-coupling. This methodology was applied to the preparation of biaryl cyclic peptides consisting of a 3-or 5-residue ring, incorporating the His residue at the N-or the C-terminus and bearing a Leu-Leu spacer or a -NH2 group at the C-terminus.In the case of the 3-residue ring peptides, the position of the His did not influence the macrocyclization.In contrast, to obtain the 5-member ring biaryl cyclic peptides, the His residue should be located at the N-terminus. It was also observed that the Leu-Leu spacer is crucial for the intramolecular arylation. These results suggest that this approach could be useful for the preparation of a diversity of synthetic and natural biaryl cyclic peptides bearing a His-Phe linkage.

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“…In order to build on their previous work employing MW-assisted Suzuki–Miyaura macrocyclization reaction [ 111 ], in 2020, Ng-Choi et al reported the MW-assisted synthesis of biaryl cyclopeptides via on-resin intramolecular Suzuki–Miyaura coupling [ 112 ]. Suzuki–Miyaura macrocyclization of 113 was performed on solid-support using Pd 2 (dba) 3 (0.2 eq), SPhos (0.4 eq), and KF (4 eq) in DME/EtOH/H 2 O (9/9/2) at 120 or 140 °C under MW irradiation for 30 min, followed by simultaneous resin cleavage and side-chain deprotections in TFA/TIS/H 2 O to provide 114 ( Scheme 33 ).…”

Section: Microwave-assisted And/or Solid-supported Synthesis Of Macro...mentioning

confidence: 99%

Recent Advances in Macrocyclic Drugs and Microwave-Assisted and/or Solid-Supported Synthesis of Macrocycles

Sun

2022

Molecules

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Macrocycles represent attractive candidates in organic synthesis and drug discovery. Since 2014, nineteen macrocyclic drugs, including three radiopharmaceuticals, have been approved by FDA for the treatment of bacterial and viral infections, cancer, obesity, immunosuppression, etc. As such, new synthetic methodologies and high throughput chemistry (e.g., microwave-assisted and/or solid-phase synthesis) to access various macrocycle entities have attracted great interest in this chemical space. This article serves as an update on our previous review related to macrocyclic drugs and new synthetic strategies toward macrocycles (Molecules, 2013, 18, 6230). In this work, I first reviewed recent FDA-approved macrocyclic drugs since 2014, followed by new advances in macrocycle synthesis using high throughput chemistry, including microwave-assisted and/or solid-supported macrocyclization strategies. Examples and highlights of macrocyclization include macrolactonization and macrolactamization, transition-metal catalyzed olefin ring-closure metathesis, intramolecular C–C and C–heteroatom cross-coupling, copper- or ruthenium-catalyzed azide–alkyne cycloaddition, intramolecular SNAr or SN2 nucleophilic substitution, condensation reaction, and multi-component reaction-mediated macrocyclization, and covering the literature since 2010.

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Solid-phase synthesis of biaryl cyclic peptides containing a histidine-tyrosine linkage

Cited by 11 publications

References 48 publications

Antifungal Peptides as Therapeutic Agents

Antifungal Peptides as Therapeutic Agents

Solid-Phase Synthesis of Biaryl Cyclic Peptides Containing a Histidine-Phenylalanine Linkage

Recent Advances in Macrocyclic Drugs and Microwave-Assisted and/or Solid-Supported Synthesis of Macrocycles

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