Preparation of the Central Tryptophan Moiety of the Celogentin/Moroidin Family of Anti-Mitotic Cyclic Peptides

Yuen, Alexander K. L.; Jolliffe, Katrina A.; Hutton, Craig A.

doi:10.1071/ch06324

Cited by 16 publications

(11 citation statements)

References 23 publications

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“…Two decades of peptide research have yielded a lot of information on the design, synthesis, and characterization of the structures of peptides. [1][2][3][4] Various polymer supports for the solid-phase synthesis of peptides have been studied. 5,6 The recent development of the incorporation of biopolymers with timeresolved fluorescence (TRF) for the imaging and therapy of tumors has become a stimulus for the design and synthesis of novel peptide polymers.…”

Section: Introductionmentioning

confidence: 99%

Convenient and efficient synthesis of a lanthanide³⁺‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Gao¹,

Handl²,

Vagner³

et al. 2007

J of Applied Polymer Sci

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To develop an assay for the cholecystokinin B receptor with an Eu 3+ -labeled cholecystokinin peptide via a diethylene triamine pentaacetic acid chelating linker, a commercial dianhydride diethylene triamine pentaacetic acid precursor was directly attached to the N-terminus of cholecystokinin peptides by a solid-phase synthesis method with a satisfactory yield and purity after reverse-phase high-performance liquid chromatography separation. Lanthanide was then coordinated to the peptide via a diethylene triamine pentaacetic acid bifunctional agent. This method is a useful approach to the large-scale synthesis of lanthanide 3+ -coordinated, diethylene triamine pentaacetic acid labeled biopolymers. This research provides not only a simple and convenient method for the preparation of lanthanide-based peptide ligand libraries but also possible lanthanide-based high-throughput screening of peptide receptors with a timeresolved fluorescence assay system. Five biopolymers were synthesized and characterized with high-resolution electrospray ionization in this study.

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Section: Introductionmentioning

confidence: 99%

Convenient and efficient synthesis of a lanthanide³⁺‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Gao¹,

Handl²,

Vagner³

et al. 2007

J of Applied Polymer Sci

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“…[6] Among these compounds, Celogentin C ( 2 , Figure 1) is most potent and inhibits tubulin polymerization with an IC 50 value of 0.8 μM. [7] Other naturally occurring bicyclic peptides include phallotoxins and amatoxins, which are isolated from poisonous mushrooms of the genus amanita. Phalloidin ( 3 , Figure 1), the first of seven bicyclic heptapeptidyl phallotoxins isolated from the death cap mushroom ( Amanita phalloides ), inhibits cytokinesis and cytotaxis by preventing the depolarization of actin filaments.…”

Section: Bicyclic Peptides In Naturementioning

confidence: 99%

Bicyclic Peptides as Next‐Generation Therapeutics

Rhodes

Pei

2017

Chemistry A European J

122

107

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Bicyclic peptides have greater conformational rigidity and metabolic stability than linear and monocyclic peptides and are capable of binding to challenging drug targets with antibody-like affinity and specificity. Powerful combinatorial library technologies have recently been developed to rapidly synthesize and screen large bicyclic peptide libraries for ligands against enzymes, receptors, and protein-protein interaction targets. Bicyclic peptides have been developed as potential therapeutics against a wide range of diseases, drug targeting agents, imaging/diagnostic probes, and research tools. In this minireview, we provide a summary of the recent progresses on the synthesis and applications of bicyclic peptides.

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“…Previous work within our group initially centred on conjugated addition of an isopropyl anion to generate the leucine-tryptophan motif, [8] analogous to Castle's radical conjugate addition methodology. However, despite modest success with model systems, functional group intolerance on the fully functionalized system led us to abandon this route.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the Leu - Trp Component of the Celogentin Family of Cyclic Peptides Through a C - H Activation - Cross-Coupling Strategy

White

Hutton

2010

Aust. J. Chem.

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A bioinspired approach to the central leucine(C3)-tryptophan(C6) cross-linked moiety present in the celogentin family of cyclic peptide natural products was achieved. The key transformation was enabled through a palladium-catalyzed C-H activation-cross-coupling of leucine quinoline amide and 6-iodotryptophan derivatives. X-Ray crystallographic analysis of a β-(indol-6-yl)-leucine derivative confirms the stereochemistry of the cross-linked adduct matches that of the natural products. The method enables the preparation of the Leu-Trp adduct as a single stereoisomer from l-leucine and l-tryptophan.

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Preparation of the Central Tryptophan Moiety of the Celogentin/Moroidin Family of Anti-Mitotic Cyclic Peptides

Abstract: The central functionalized tryptophan core of the celogentin/moroidin family of cyclic peptides has been prepared. The strategy incorporates a novel preparation of 4-iodobenzaldehyde and employs a Larock annulation as the key step.

Cited by 16 publications

References 23 publications

Convenient and efficient synthesis of a lanthanide³⁺‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Convenient and efficient synthesis of a lanthanide³⁺‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Bicyclic Peptides as Next‐Generation Therapeutics

Synthesis of the Leu - Trp Component of the Celogentin Family of Cyclic Peptides Through a C - H Activation - Cross-Coupling Strategy

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Preparation of the Central Tryptophan Moiety of the Celogentin/Moroidin Family of Anti-Mitotic Cyclic Peptides

Abstract: The central functionalized tryptophan core of the celogentin/moroidin family of cyclic peptides has been prepared. The strategy incorporates a novel preparation of 4-iodobenzaldehyde and employs a Larock annulation as the key step.

Cited by 16 publications

References 23 publications

Convenient and efficient synthesis of a lanthanide3+‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Convenient and efficient synthesis of a lanthanide3+‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Bicyclic Peptides as Next‐Generation Therapeutics

Synthesis of the Leu - Trp Component of the Celogentin Family of Cyclic Peptides Through a C - H Activation - Cross-Coupling Strategy

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Product

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About

Convenient and efficient synthesis of a lanthanide³⁺‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor

Convenient and efficient synthesis of a lanthanide³⁺‐coordinated, diethylene triamine pentaacetic acid labeled biopolymer as an assay for the cholecystokinin B receptor