Total Synthesis of Keramamides A and L from a Common Precursor by Late‐Stage Indole Synthesis and Configurational Revision

Junk, Lukas; Kazmaier, Uli

doi:10.1002/anie.201806657

Cited by 28 publications

(21 citation statements)

References 53 publications

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“…Concerning our ongoing interest into the syntheses of biological active natural products [25][26][27][28][29][30] we also focused on the synthesis of chondramide derivatives 31,32 and we developed a straightforward protocol towards the miuraenamides 33 based on a late stage modification approach. 34 This concept allowed the synthesis of a small library of miuraenamide derivatives via aldol reaction at the C-terminal position of a glycine containing cyclodepsipeptide (Scheme 1).…”

Section: Resultsmentioning

confidence: 99%

Synthesis of modified miuraenamides – the Ugi approach

Kappler¹,

Kazmaier²

2021

Arkivoc

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Miuraenamides, a group of marine cyclodepsipeptides, closely related to jasplakinolide and geodiamolide are found to accelerate nucleation and polymerization of actin, and therefore interfere with cell division processes, at concentrations in the low nanomolar range. For SAR studies derivatives are synthesized via Ugi reaction, which provides the complete tripeptide fragment in only one step. While a wide range of modifications are possible at the C-terminus of the peptide, variations at the central position are not tolerated. Neither modifications in the polyketide.

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Section: Resultsmentioning

confidence: 99%

Synthesis of modified miuraenamides – the Ugi approach

Kappler¹,

Kazmaier²

2021

Arkivoc

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“…Keramamides M and N showed moderate cytotoxicities against L1210 (IC 50 = 2.02 and 2.33 µM, respectively) and KB (IC 50 = 5.05 and 6.23 µM, respectively) cells [ 74 ]. The total synthesis of different keramamides had been completed by the same research group [ 75 ]. From the results of structural elucidation, some intriguing constituents of these cyclic peptides exhibited anticancer potentials against some other cancer cell lines.…”

Section: Marine-derived Anticancer Cyclopeptidesmentioning

confidence: 99%

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

Zhang

Xia

Zhang

2021

IJMS

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Cyclopeptides or cyclic peptides are polypeptides formed by ring closing of terminal amino acids. A large number of natural cyclopeptides have been reported to be highly effective against different cancer cells, some of which are renowned for their clinical uses. Compared to linear peptides, cyclopeptides have absolute advantages of structural rigidity, biochemical stability, binding affinity as well as membrane permeability, which contribute greatly to their anticancer potency. Therefore, the discovery and development of natural cyclopeptides as anticancer agents remains attractive to academic researchers and pharmaceutical companies. Herein, we provide an overview of anticancer cyclopeptides that were discovered in the past 20 years. The present review mainly focuses on the anticancer efficacies, mechanisms of action and chemical structures of cyclopeptides with natural origins. Additionally, studies of the structure–activity relationship, total synthetic strategies as well as bioactivities of natural cyclopeptides are also included in this article. In conclusion, due to their characteristic structural features, natural cyclopeptides have great potential to be developed as anticancer agents. Indeed, they can also serve as excellent scaffolds for the synthesis of novel derivatives for combating cancerous pathologies.

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“…Thus, we envisioned a strategy based on late-stage hydrostannation of a propargylic residue. 81 The propargylglycine-containing cyclic peptide was prepared by standard methods and was subjected to Rucatalyzed hydrostannation 82 to access the requisite stannylated residue (Scheme 19). This reaction proceeded smoothly and provided the stannylated peptide regioselectively.…”

Section: Account Syn Lettmentioning

confidence: 99%

Peptide Modifications: Versatile Tools in Peptide and Natural Product Syntheses

Servatius¹,

Junk²,

Kazmaier³

2019

Synlett

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Peptide modifications via C–C bond formation have emerged as valuable tools for the preparation and alteration of non-proteinogenic amino acids and the corresponding peptides. Modification of glycine subunits in peptides allows for the incorporation of unusual side chains, often in a highly stereoselective manner, orchestrated by the chiral peptide backbone. Moreover, modifications of peptides are not limited to the peptidic backbone. Many side-chain modifications, not only by variation of existing functional groups, but also by C–H functionalization, have been developed over the past decade. This account highlights the synthetic contributions made by our group and others to the field of peptide modifications and their application in natural product syntheses.1 Introduction2 Peptide Backbone Modifications via Peptide Enolates2.1 Chelate Enolate Claisen Rearrangements2.2 Allylic Alkylations2.3 Miscellaneous Modifications3 Side-Chain Modifications3.1 C–H Activation3.1.1 Functionalization via Csp3–H Bond Activation3.2.2 Functionalization via Csp2–H Bond Activation3.2 On Peptide Tryptophan Syntheses4 Conclusion

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Total Synthesis of Keramamides A and L from a Common Precursor by Late‐Stage Indole Synthesis and Configurational Revision

Cited by 28 publications

References 53 publications

Synthesis of modified miuraenamides – the Ugi approach

Synthesis of modified miuraenamides – the Ugi approach

Natural Cyclopeptides as Anticancer Agents in the Last 20 Years

Peptide Modifications: Versatile Tools in Peptide and Natural Product Syntheses

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