The unexpected isolation of CTP-431, a novel thiopyrone from the sponge Cacospongia mycofijiensis

The Journal of Organic Chemistry
Tyler A JohnsonPhillip Crews

Abstract

A reinvestigation of a Fijian collection of Cacospongia mycofijiensis has yielded the known mycothiazole and a novel heterocyclic, CTP-431 (1). Its structure including absolute configuration as 8R,9R,10S,13S was established using NMR data, calculated DFT (13)C chemical shifts and results from X-ray crystallography. It is possible that the tricyclic skeleton of CTP-431 (1) is biosynthetically related to the macrolide latrunculin A, however the thiopyrone moiety of 1 has no previous precedent in natural products chemistry.

References

Dec 21, 2002·The Journal of Organic Chemistry·Zia ThalePhillip Crews
Jun 26, 2004·Journal of Natural Products·Boaz ViloznyPhillip Crews
Jan 31, 2006·Journal of Natural Products·Rachel N SonnenscheinPhillip Crews
Jun 2, 2007·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Y AtalayD Avci
Jul 12, 2007·Journal of Medicinal Chemistry·Tyler A JohnsonPhillip Crews
Feb 29, 2008·Journal of the American Chemical Society·Amy B DounayAaron D Wrobleski

❮ Previous
Next ❯

Citations

Dec 2, 2011·Journal of Natural Products·Tyler A JohnsonPhillip Crews
Apr 18, 2009·Magnetic Resonance in Chemistry : MRC·Marcelo A Muñoz, Pedro Joseph-Nathan
Jan 29, 2010·Magnetic Resonance in Chemistry : MRC·Mikhail ElyashbergAntony Williams
Jan 30, 2010·Natural Product Reports·John W BluntMichèle R Prinsep
May 19, 2010·Natural Product Reports·Mikhail ElyashbergKirill Blinov
Sep 15, 2012·Natural Product Reports·Klaus-Dieter FeussnerChris M Ireland
Jul 26, 2018·The Journal of Organic Chemistry·Adam D PrzeslakChristopher J Moody

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.