Stereospecific Total Synthesis of Somocystinamide A

Suyama, Takashi; Gerwick, William H.

doi:10.1021/ol8016947

Cited by 29 publications

(18 citation statements)

References 38 publications

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“…Furthermore, low application of compound 77 at 100 pmol inhibited the growth of caspase-8-expressing tumor cells in an in vivo system using chick chorioallantoic membrane seeded with neuroblastoma tumors. The total synthesis of this very important molecule was recently accomplished by Suyama and Gerwick (2008).…”

Section: Apratoxins and Analoguesmentioning

confidence: 99%

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

2010

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Section: Apratoxins and Analoguesmentioning

confidence: 99%

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

2010

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“…Despite being prolific producers of secondary metabolites, a complete lack of genetic techniques for filamentous marine cyanobacteria that are rich in natural products has, in contrast to other bacterial sources of natural products, limited access to increased supplies of these secondary metabolites. In vivo and other detailed studies of the biological properties of these compounds have instead resulted from repeated and often large-scale field collections, longer-term culture efforts [8] or sophisticated synthetic methods [9]. Filamentous marine cyanobacteria such as Moorea (formerly Lyngbya sp.)…”

Section: Introductionmentioning

confidence: 99%

Evaluation of Streptomyces coelicolor A3(2) as a heterologous expression host for the cyanobacterial protein kinase C activator lyngbyatoxin A

et al. 2012

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Filamentous marine cyanobacteria are extremely rich sources of bioactive natural products and often employ highly unusual biosynthetic enzymes in their assembly. However, the current lack of techniques for stable DNA transfer into these filamentous organisms, combined with the absence of heterologous expression strategies for nonribosomal cyanobacterial gene clusters, prohibit the creation of mutant strains or the heterologous production of these cyanobacterial compounds in other bacteria. In this study, we evaluated the capability of a derivative of the model actinomycete Streptomyces coelicolor A3(2) to express enzymes involved in the biosynthesis of the protein kinase C activator lyngbyatoxin A from a Hawaiian strain of Moorea producta (previously classified as Lyngbya majuscula). Despite large differences in GC content between these two bacteria and the presence of rare TTA/UUA leucine codons in lyngbyatoxin ORFs we were able to achieve expression of the cytochrome P450 monooxygenase LtxB and reverse prenyltransferase LtxC in S. coelicolor M512 and confirmed the in vitro functionality of S. coelicolor overexpressed LtxC. Attempts to express the entire lyngbyatoxin A gene cluster in S. coelicolor M512 were not successful because of transcript termination observed for the ltxA gene, which encodes a large nonribosomal peptide synthetase. However, these attempts did show a detectable level of cyanobacterial promoter recognition in Streptomyces. Successful expression of lyngbyatoxin A proteins in Streptomyces provides a new platform for biochemical investigation of natural product enzymes from Moorea strains.

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“…Moreover, a naturally occurring symmetrical disulfide dimer lipid 1 containing a dithiodipropionic acid structure is rare in natural environment. A limited number of symmetrical disulfide compounds have been previously isolated from marine sources [26,27], a basidiomycete mushroom of the Cortinarius genus [28], and plants of the Allium genus [29,30]. Interestingly, the isolation and structural elucidation of three co-metabolites, a pregnane derivative 5,16-pregnadien-3b-ol-20-one acetate (2) and two ergosterol congeners appear to lend support for a shared steroidal nucleus produced via a biosynthetic pathway.…”

Section: Resultsmentioning

confidence: 99%

Metabolites from an Endophytic Fungus Sphaceloma sp. LN‐15 Isolated from the Leaves of Melia azedarach

Zhang

Gao

et al. 2009

Lipids

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Two new natural compounds, a symmetrical disulfide dimer didodecyl 3,3''-dithiodipropionate (1) and a pregnane steroid 5,16-pregnadien-3beta-ol-20-one acetate (2), were isolated together with two known compounds, ergosta-4,6,8(14),22-tetraen-3-one (3) and ergosterol peroxide (4), from the ethyl acetate soluble extract of fermentation broth of an endophytic fungus, Sphaceloma sp. LN-15 isolated from the leaves of Melia azedarach L. and grown in pure culture. Their structures were determined on the basis of spectroscopic methods including 1D and 2D nuclear magnetic resonance spectroscopy (NMR) experiments and by mass spectrometric measurements (MS). These fungal metabolites were isolated for the first time from the genus Sphaceloma. The structure of 1 was also confirmed by chemical synthesis.

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Stereospecific Total Synthesis of Somocystinamide A

Cited by 29 publications

References 38 publications

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

Filamentous tropical marine cyanobacteria: a rich source of natural products for anticancer drug discovery

Evaluation of Streptomyces coelicolor A3(2) as a heterologous expression host for the cyanobacterial protein kinase C activator lyngbyatoxin A

Metabolites from an Endophytic Fungus Sphaceloma sp. LN‐15 Isolated from the Leaves of Melia azedarach

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