Case Studies of the Synthesis of Bioactive Cyclodepsipeptide Natural Products

Stolze, Sara C.; Kaiser, Markus

doi:10.3390/molecules18021337

Cited by 29 publications

(7 citation statements)

References 76 publications

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“…[1][2][3] The cyclodepsipeptides contain a hydroxy acid that bears one or more chiral centers, and also often contain N-methylamino acids, which significantly increases the structural diversity of these compounds. The ester linkage between a hydroxy acid and an amino acid is also a unique structural feature.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of the Biologically Active Natural Product Cyclodepsipeptides Apratoxin A and Its Analogues

Doi

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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This paper describes the synthetic studies conducted on a marine natural product, cyclodepsipeptide apratoxin A. Total synthesis of the oxazoline analogue of apratoxin A was achieved. The conversion of oxazoline to thioamide, as well as thioamide formation from a serine-derived compound, were both unsuccessful. However, thiazoline formation from a cysteine-derived compound led to the total synthesis of apratoxin A. An in vivo study on synthetic apratoxin A revealed that it has potent antitumor activity, but with significant toxicity. Solid-phase synthesis of apratoxin A was accomplished using a preformed thiazoline derivative as a coupling unit. This method was used to synthesize several azido-containing analogues as precursors of molecular probes, and these analogues exhibited potent biological activity.

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Section: Introductionmentioning

confidence: 99%

Synthesis of the Biologically Active Natural Product Cyclodepsipeptides Apratoxin A and Its Analogues

Doi

2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…To solve this problem, sufficient compound material was however required. Facing the problem, total synthesis and heterologous expression of genes or gene clusters in microbial hosts were two better ways, which were keys to access industrially and pharmaceutically relevant compounds in an economically affordable and sustainable manner ( Stolze and Kaiser, 2013 ; Doi, 2014 ; Roderich et al, 2015 ).…”

Section: Discussionmentioning

confidence: 99%

Recent advances on cyclodepsipeptides: biologically active compounds for drug research

Liu,

Ou-Yang,

et al. 2023

Front. Microbiol.

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Cyclodepsipeptides are a large family of peptide-related natural products consisting of hydroxy and amino acids linked by amide and ester bonds. A number of cyclodepsipeptides have been isolated and characterized from fungi and bacteria. Most of them showed antitumor, antifungal, antiviral, antimalarial, and antitrypanosomal properties. Herein, this review summarizes the recent literatures (2010–2022) on the progress of cyclodepsipeptides from fungi and bacteria except for those of marine origin, in order to enrich our knowledge about their structural features and biological sources.

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“…Moreover, cyclic depsipeptides also exhibit a better resistance profile to proteases than their linear counterparts [18]. A large variety of bioactive cyclic depsipeptides have been isolated and characterized, which occupy therapeutically relevant chemical space that could lead to the discovery of new biology, chemical tools, or even drug leads [19][20][21][22][23][24].…”

Section: Introductionmentioning

confidence: 99%

Total Syntheses of Colletopeptide A and Colletotrichamide A

Chen,

Jiang,

Yan

et al. 2023

Molecules

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The first total syntheses of cyclic depsipeptides colletopeptide A and colletotrichamide A, have been accomplished. The key advanced intermediate, a cyclic tridepsipeptide derivative, was constructed using a sequence of transformations that features asymmetric Brown crotylation, cross metathesis, Yamaguchi esterification, ozonolysis, and macrolactamization. A late-stage incorporation of the mannose fragment completed the synthesis of colletotrichamide A, and the desilylation of the common intermediate gave rise to colletopeptide A, which led to unambiguous confirmation of the absolute stereochemistry of the aforementioned natural products.

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Case Studies of the Synthesis of Bioactive Cyclodepsipeptide Natural Products

Cited by 29 publications

References 76 publications

Synthesis of the Biologically Active Natural Product Cyclodepsipeptides Apratoxin A and Its Analogues

Synthesis of the Biologically Active Natural Product Cyclodepsipeptides Apratoxin A and Its Analogues

Recent advances on cyclodepsipeptides: biologically active compounds for drug research

Total Syntheses of Colletopeptide A and Colletotrichamide A

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