Isolation, structural determination and synthetic approaches toward amphidinol 3

Bensoussan, Charlélie; Rival, Nicolas; Hanquet, Gilles; Colobert, Françoise; Reymond, Sébastien; Cossy, Janine

doi:10.1039/c3np70062c

Cited by 20 publications

(10 citation statements)

References 156 publications

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“…The relative synonymous codon usage (RSCU) was calculated using the software codonW for a subset of annotated genes from each transcriptome, and comparisons were made across all species as well as for each sequence within each species looking for populations of RNA sequences with the hallmarks of codon bias [21]. Gene selection and species comparisons were anchored methodologically using Amphidinium carterae because it is the most basal photosynthetic core dinoflagellate, a toxin producer, and has a well assembled transcriptome (Genbank accession #SRX722011) [22,23]. Because these analyses are based on codon abundance it is critical that protein coding sequences in the proper reading frame are used.…”

Section: Introductionmentioning

confidence: 99%

Transcriptome Analysis of Core Dinoflagellates Reveals a Universal Bias towards “GC” Rich Codons

2017

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Although dinoflagellates are a potential source of pharmaceuticals and natural products, the mechanisms for regulating and producing these compounds are largely unknown because of extensive post-transcriptional control of gene expression. One well-documented mechanism for controlling gene expression during translation is codon bias, whereby specific codons slow or even terminate protein synthesis. Approximately 10,000 annotatable genes from fifteen “core” dinoflagellate transcriptomes along a range of overall guanine and cytosine (GC) content were used for codonW analysis to determine the relative synonymous codon usage (RSCU) and the GC content at each codon position. GC bias in the analyzed dataset and at the third codon position varied from 51% and 54% to 66% and 88%, respectively. Codons poor in GC were observed to be universally absent, but bias was most pronounced for codons ending in uracil followed by adenine (UA). GC bias at the third codon position was able to explain low abundance codons as well as the low effective number of codons. Thus, we propose that a bias towards codons rich in GC bases is a universal feature of core dinoflagellates, possibly relating to their unique chromosome structure, and not likely a major mechanism for controlling gene expression.

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Section: Introductionmentioning

confidence: 99%

Transcriptome Analysis of Core Dinoflagellates Reveals a Universal Bias towards “GC” Rich Codons

2017

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“…The unique structural features of AM3, represented by the presence of a long hydrophilic polyol chain, highly substituted THP ring systems, and a hydrophobic polyene unit, have attracted considerable attention in the synthetic community . Pioneering synthetic studies of the partial structure of AM3 containing THP ring(s) and the polyene chain were reported by Rychnovsky et al (C31–C67 fragment), Roush et al, (C43–C67 fragment), and Paquette et al (C43–C67 fragment).…”

Section: Figurementioning

confidence: 99%

Synthesis and Stereochemical Revision of the C31–C67 Fragment of Amphidinol 3

et al. 2018

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Amphidinol 3( AM3) is am arine natural product produced by the dinoflagellate Amphidinium klebsii. Although the absolute configuration of AM3 was determined in 1999 by extensive NMR analysis and degradation of the natural product, it was adaunting task because of the presence of numerous stereogenic centers on the acyclic carbon chain and the limited availability from natural sources.T hereafter, revisions of the absolute configurations at C2 and C51 were reported in 2008 and 2013, respectively.Reported herein is the revised absolute configuration of AM3:3 2S,3 3R, 34S,3 5S, 36S,a nd 38S based on the chemical synthesis of partial structures corresponding to the C31-C67 fragment of AM3 in combination with degradation of the natural product. The revised structure is unique in that both antipodal tetrahydropyran counterparts exist on as ingle carbon chain. The structural revision of AM3 may affect proposed structures of congeners related to the amphidinols.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: https://doi.

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“…, proposed the revised structure of amphidinol 3 and its absolute configuration was found to be ( R ) at C(2). Owing to its complex structure and inherent biological activity, the synthesis of amphidinol 3 ( 1 ) has received special attention . In continuation of our efforts toward the synthesis of complex natural products , we herein report a stereoselective approach for the synthesis of the C(1) – C(28) side chain of amphidinol 3 ( 1 ; Fig.…”

Section: Introductionmentioning

confidence: 99%

Stereoselective Synthesis of the C(1) - C(28) Fragment of Amphidinol 3

et al. 2016

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A stereoselective synthesis of the polyol side chain (C(1) – C(28)) of amphidinol 3 has been accomplished following Sharpless epoxidation, Crimmins aldol reaction, Jacobsen kinetic resolution, Sharpless asymmetric dihydroxylation, and our own reaction for the synthesis of a chiral allylic alcohol from an epoxy alcohol. The olefin functionality was introduced by a cross metathesis and Julia–Kocienski olefination.

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Isolation, structural determination and synthetic approaches toward amphidinol 3

Abstract: This review highlights the isolation and the structural determination of amphidinol 3 (AM3), as well as the synthetic efforts to its preparation. The mechanism of action of AM3 will not be developed herein.

Cited by 20 publications

References 156 publications

Transcriptome Analysis of Core Dinoflagellates Reveals a Universal Bias towards “GC” Rich Codons

Transcriptome Analysis of Core Dinoflagellates Reveals a Universal Bias towards “GC” Rich Codons

Synthesis and Stereochemical Revision of the C31–C67 Fragment of Amphidinol 3

Stereoselective Synthesis of the C(1) - C(28) Fragment of Amphidinol 3

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