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Hill, Robert A.; Sutherland, Andrew

doi:10.1039/d3np90007j

Cited by 3 publications

(2 citation statements)

References 34 publications

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“…There is high biological and synthetic interest in many thiazole-and thiazoline-containing natural products, such as thiangazole, [1] didehydromirabazole, [2] baringolin, [3] and apratoxin, [4] due to their striking tumor-selective cytotoxicity, antibiotic and/or antiviral activities. The recently highlighted [5] thiamyxins represent a new group of thiazole/ thiazoline-rich natural products, isolated from a myxobacterial strain of the Myxococcaceae family (MCy9487) by Müller and co-workers. [6] The depsipeptides appear in their cyclic form, thiamyxin A and B, as well as the open-chain hydroxy acid thiamyxin C and as the corresponding glycerol ester thiamyxin D (Figure 1).…”

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confidence: 99%

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Bauer

Kazmaier

2023

Angew Chem Int Ed

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We present the first total synthesis of the thiamyxins A–C and the now fully characterized thiamyxin E, an interesting class of thiazole‐ and thiazoline‐rich depsipeptides with diverse antiviral activity. The synthesis features a parallel closing of two methyl thiazoline units, with low epimerization of the very labile adjacent stereocenter. It also includes the three‐step synthesis of an uncommon hydroxy acid and the oxidation‐free elimination of a phenylselenide to form a dehydroalanine moiety. The exploitation of the acid‐labile stereocenter at the isoleucine moiety and the reopening of the macrolactones gave access to the four thiamyxins with good yields and diastereomeric purities from a single precursor. The modular total synthesis allows further testing of the biological activity and gives opportunities to explore the pharmacophore and antiviral target through derivatization.

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confidence: 99%

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Bauer

Kazmaier

2023

Angew Chem Int Ed

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“…Viele thiazol-und thiazolinhaltige Naturstoffe wie Thiangazol, [1] Didehydromirabazol, [2] Baringolin, [3] und Apratoxin [4] sind aufgrund ihrer bemerkenswerten tumorselektiven Cytotoxizität, antibiotischen und/oder antiviralen Aktivitäten, von hohem biologischen und synthetischen Interesse. Die kürzlich vorgestellten [5] Thiamyxine stellen eine neue Gruppe von thiazol-/thiazolinreichen Naturstoffen dar, die von Müller et al aus einem Myxobakterienstamm (MCy9487) der Familie der Myxococcaceae isoliert wurden. [6] Diese Depsipeptide kommen sowohl in einer makrocyclischen Form (Thiamyxin A und B) als auch in einer offenkettigen Form als Hydroxysäure (Thiamyxin C) oder Glycerinester (Thiamyxin D) vor (Abbildung 1).…”

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Totalsynthese von Thiamyxin A–C und Thiamyxin E, potente RNA‐Virus inhibierende (Cyclo)depsipeptide

Bauer

Kazmaier

2023

Angewandte Chemie

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Wir präsentieren die erste Totalsynthese der Thiamyxine A-C und des jetzt vollständig charakterisierten Thiamyxins E, einer interessanten Klasse thiazolund thiazolinreicher Depsipeptide mit vielfältiger antiviraler Aktivität. Die Synthese zeichnet sich aus durch einen parallelen Ringschluss zu zwei Methylthiazolin-Einheiten unter geringer Epimerisierung des sehr labilen benachbarten stereogenen Zentrums. Des Weiteren wird die dreistufige Synthese einer ungewöhnlichen Hydroxysäure sowie die oxidationsfreie Eliminierung eines Phenylselenids zum Dehydroalanin gezeigt. Die Ausnutzung des säurelabilen Stereozentrums am Isoleucin-Rest und die erneute Öffnung der Makrolactone ermöglichen den Zugang zu den vier Thiamyxinen in guten Ausbeuten und Diastereomerenverhältnissen aus einem einzigen Vorläufer. Durch die modular gestaltete Totalsynthese sind weitere Bioaktivitätstests und die Erforschung eines Pharmakophors über die Synthese weiterer Derivate möglich.

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Computer Science Technology in Natural Products Research: A Review of Its Applications and Implications

Ogawa

Daiki

Hosoki

2023

CHEMICAL & PHARMACEUTICAL BULLETIN

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Computational approaches to drug development are rapidly growing in popularity and have been usedto produce significant results. Recent developments in information science have expanded databases and chemical informatics knowledge relating to natural products. Natural products have long been well-studied, and a large number of unique structures and remarkable active substances have been reported. Analyzing accumulated natural product knowledge using emerging computational science techniques is expected to yield more new discoveries. In this article, we discuss the current state of natural product research using machine learning. The basic concepts and frameworks of machine learning are summarized. Natural product research that utilizes machine learning is described in terms of the exploration of active compounds, automatic compound design, and application to spectral data. In addition, efforts to develop drugs for intractable diseases will be addressed. Lastly, we discuss key considerations for applying machine learning in this field. This paper aims to promote progress in natural product research by presenting the current state of computational science and chemoinformatics approaches in terms of its applications, strengths, limitations, and implications for the field.

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Abstract: A personal selection of 32 recent papers is presented covering various aspects of current developments in bioorganic chemistry and novel natural products, such as euphylonoid A from Euphorbia hylonoma.

Cited by 3 publications

References 34 publications

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Total Synthesis of Thiamyxins A–C and Thiamyxin E, a Potent Class of RNA‐Virus‐Inhibiting (Cyclo)depsipeptides

Totalsynthese von Thiamyxin A–C und Thiamyxin E, potente RNA‐Virus inhibierende (Cyclo)depsipeptide

Computer Science Technology in Natural Products Research: A Review of Its Applications and Implications

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