Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides

García-Pindado, Júlia; Willemse, Tom; Goss, Rebecca J. M.; Maes, Bert U. W.; Giralt, Ernest; Ballet, Steven; Teixidó, Meritxell

doi:10.1002/bip.23112

Cited by 12 publications

(20 citation statements)

References 35 publications

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“…in 2017, in which the cross‐coupling reaction took place between a boronophenylalanine and a iodophenylalanine to generate the biaryl bridge on resin . This approach was extended to bromotryptophan containing peptides in 2018 . The methodology comprises an on‐resin Miyaura borylation of the first introduced bromotryptophan followed by completion of the linear precursor sequence including the second bromotryptophan moiety.…”

Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

“…Reaction conditions: A) Pd(PPh 3 ) 4 (10 mol %), Cs 2 CO 3 (3 equiv), DMF, 60 °C, 72 h. B) TFA:H 2 O:TIS 95:2.5:2.5. C) PyBOP, HOAt, DCM with 1 % DMF, RT, 24–48 h. D) NaS 2 O 4 , H 2 O/ACN/EtOH 1:1:1, 48 h …”

Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

“…As a result, the 7,7‐bicyclic peptide showed the highest transport rate in a parallel artificial membrane permeability assay, which is a model for the BBB. The serum stability of the bicyclic tryptophan peptides was not investigated . However, the previous study on a bicyclic peptide with a phenylalanine–phenylalanine biaryl bridge did not show any significant degradation in human serum within 24 h …”

Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

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Late‐Stage Diversification of Tryptophan‐Derived Biomolecules

Gruß

Sewald

2020

Chemistry A European J

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Pd-mediated reactions have emergeda sapowerful tool for the site-selective and bioorthogonall ate-stage diversification of amino acids, peptides and related compounds. Indole moieties of tryptophan derivatives are susceptible to C 2 H-activation, whereas halogenated aromatic amino acids such as halophenylalanines or halotryptophans provide ab road spectrum of different functionalisations. The compatibility of transition-metal-catalysed cross-couplings with functional groups in peptides, other biologically active compoundsa nd even proteins hasb een demonstrated. ThisReview primarily compiles the applicationo fd ifferent crosscoupling reactions to modify halotryptophans,h alotryptophan containing peptides or halogenated, biologically active compounds derived from tryptophan. Moderna pproaches use regio-and stereoselective biocatalytic strategies to generate halotryptophans and derivatives on ap reparative scale. The combination of bio-and chemocatalysis in cascade reactions is given by the biocompatibility and bioorthogonality of Pd-mediated reactions. Pd-Catalysed C 2 ÀHA ctivationo fT ryptophansThe C 2 position of indoles and tryptophans can be selectively addressed by transition-metal-catalysed C(sp 2 )ÀHa ctiva- [a] H. Gruß,P rof. Dr.N.S ewald

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Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

Section: Suzuki–miyaura Cross‐couplingmentioning

confidence: 99%

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Late‐Stage Diversification of Tryptophan‐Derived Biomolecules

Gruß

Sewald

2020

Chemistry A European J

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“…In this context, herein our aim was to extend our expertise in the formation of biaryl linkages to the solid-phase synthesis of biaryl bicyclic peptides. To the best of our knowledge, there is only one example on the preparation of this type of compounds on solid support, even though the final cyclization was performed in solution [24–25]. In contrast, in the present study we envisaged a synthetic strategy for the preparation of biaryl bicyclic peptides in which all the steps would be carried out on solid phase.…”

Section: Introductionmentioning

confidence: 99%

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

Ng-Choi¹,

Oliveras²,

Feliu³

et al. 2019

Beilstein J. Org. Chem.

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A methodology for the solid-phase synthesis of biaryl bicyclic peptides containing a Phe-Phe, a Phe-Tyr or a Tyr-Tyr motif has been devised. This approach comprises two key steps. The first one involves the cyclization of a linear peptidyl resin containing the corresponding halo- and boronoamino acids via a microwave-assisted Suzuki–Miyaura cross coupling. This step is followed by the macrolactamization of the resulting biaryl monocyclic peptidyl resin leading to the formation of the expected biaryl bicyclic peptide. This study provides the first solid-phase synthesis of this type of bicyclic compounds being amenable to prepare a diversity of synthetic or natural biaryl bicyclic peptides.

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“…[34] The use of an intramolecular Suzuki-Miyaura reactionp erformedo n-resin to form Trp-Trpc yclic peptides showed the potential to improve biological properties by extending the p-system. [35] Moreover,S uzuki-Miyaura cross-couplingr esulted in as idec hain-to-tail-cyclized RGD peptides with biaryl moieties, providing an ew dimension of structure-activity relationships. [36] We additionally envisaged exploring the use of intramolecular Suzuki-Miyaurac ross-coupling on resin between 7-bromotryptophan and phenothiazine (Ptz) boronic acids to build novel bioactive and fluorescent cyclic RGDderivatives, c(RGD(W/w)(7-3-Ptz)) (Scheme1).…”

Section: Introductionmentioning

confidence: 99%

Phenothiazine‐Biaryl‐Containing Fluorescent RGD Peptides

Ghabraie

Kemker

Tonali

et al. 2020

Chemistry A European J

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Cyclic RGD peptides are well‐known ligands of integrins. The integrins αVβ3 and α5β1 are involved in angiogenesis, and integrin αVβ3 is abundantly present on cancer cells, thus representing a therapeutic target. Hence, synthetic and biophysical studies continuously are being directed towards the understanding of ligand‐integrin interaction. In this context, the development of versatile synthetic strategies to obtain fluorescent building blocks that can add molecular diversity and modular spectral characteristics while not compromising binding affinity or selectivity is a relevant task. An on‐resin intramolecular Suzuki–Miyaura cross‐coupling (SMC) between l‐ or d‐7‐bromotryptophan (7BrTrp) and a phenothiazine (Ptz) boronic acid affords fluorescent cyclic RGD pseudopeptides, c(RGD(W/w)Ptz). Ring closure by SMC establishes a phenothiazine–indole moiety with axial chirality. An array of eight novel compounds has been synthesized, among them one fluorescent compound with good affinity to integrin αVβ3. The fluorescence properties of the analogues can be efficiently tuned depending on the substituents in Ptz moiety even for fluorescence emission in the visible (red) spectral range.

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Bromotryptophans and their incorporation in cyclic and bicyclic privileged peptides

Cited by 12 publications

References 35 publications

Late‐Stage Diversification of Tryptophan‐Derived Biomolecules

Late‐Stage Diversification of Tryptophan‐Derived Biomolecules

Solid-phase synthesis of biaryl bicyclic peptides containing a 3-aryltyrosine or a 4-arylphenylalanine moiety

Phenothiazine‐Biaryl‐Containing Fluorescent RGD Peptides

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