Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A new member of the fusaricidin family - structure elucidation and synthesis of fusaricidin E.

ABSTRACT: Two hitherto unknown fusaricidins were obtained from fermentation broths of three Paenibacillus strains. After structure elucidation based on tandem mass spectrometry and NMR spectroscopy, fusaricidin E was synthesized to confirm the structure and the suggested stereochemistry. The synthesis was based on a new strategy which includes an efficient access to the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain from erucamide.

SUBMITTER: Reimann M

PROVIDER: S-EPMC5530608 | biostudies-literature | 2017

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

A new member of the fusaricidin family - structure elucidation and synthesis of fusaricidin E.

Reimann Marcel M Sandjo Louis P LP Antelo Luis L Thines Eckhard E Siepe Isabella I Opatz Till T

Beilstein journal of organic chemistry 20170720

Two hitherto unknown fusaricidins were obtained from fermentation broths of three <i>Paenibacillus</i> strains. After structure elucidation based on tandem mass spectrometry and NMR spectroscopy, fusaricidin E was synthesized to confirm the structure and the suggested stereochemistry. The synthesis was based on a new strategy which includes an efficient access to the 15-guanidino-3-hydroxypentadecanoyl (GHPD) side chain from erucamide. ...[more]

PMID: 28781709

Similar Datasets

Studies toward the unique pederin family member psymberin: full structure elucidation, two alternative total syntheses, and analogs.

Project description:Two synthetic approaches to psymberin have been accomplished. A highly convergent first generation synthesis led to the complete stereochemical assignment and demonstrated that psymberin and irciniastatin A are identical compounds. This synthesis featured a diastereoselective aldol coupling between the aryl fragment and a central tetrahydropyran core and a novel one-pot procedure to convert an amide, via intermediacy of a sensitive methyl imidate, to the N-acyl aminal reminiscent of psymberin. The highlights of the second generation synthesis include an efficient iridium-catalyzed enantioselective bisallylation of neopentyl glycol and a stepwise Sonogashira coupling/cycloisomerization/reduction sequence to construct the dihydroisocoumarin unit. The two synthetic avenues were achieved in 17-18 steps (longest linear sequence, ~14-15 isolations) from 3 fragments prepared in 7-8 (first generation) and 3-8 (second generation) steps each. This convergent approach allowed for the preparation of sufficient amounts of psymberin (~ 0.5 g) for follow-up biological studies. Meanwhile, our highly flexible strategy enabled the design and synthesis of multiple analogs, including a psymberin-pederin hybrid, termed psympederin, that proved crucial to a comprehensive understanding of the chemical biology of psymberin and related compounds that will be described in a subsequent manuscript.

| S-EPMC3482988 | biostudies-literature

Crystal structure of KNaCuP2O7, a new member of the diphosphate family.

Project description:Potassium sodium copper(II) diphosphate(V), KNaCuP2O7, was synthesized by solid-state reactions. It crystallizes in the α-Na2CuP2O7 structure type in space group P21/n. In the crystal, CuO5 square-pyramids are linked to nearly eclipsed P2O7 groups by sharing corners to build up corrugated layers with composition [CuP2O7]2- that extend parallel to (010). The K+ and Na+ cations reside in the inter-layer space and are connected to nine and seven O atoms, respectively. The structural model was validated by bond-valence-sum (BVS) and charge-distribution (CHARDI) analysis.

| S-EPMC5956317 | biostudies-literature

Crystal structure of CsCrAs2O7, a new member of the diarsenate family.

Project description:Caesium chromium(III) diarsenate(V), CsCrAs2O7, was prepared by solid-state reactions. The title structure consists of isolated CrO6 octa-hedra and As2O7 diarsenate groups, sharing corners to build up a three-dimensional [CrAs2O7](-) anionic framework. In this framework, channels extending parallel to [001] are present in which the ten-coordinate Cs(+) ions reside. CsCrAs2O7 is isotypic with the monoclinic A (I) M (III) X 2O7 (A (I) = alkali metal; M (III) = Al, Cr, Fe; X = As, P) type I family of compounds crystallizing in the space group P21/c.

| S-EPMC4459375 | biostudies-literature

Structure of armadillo ACBP: a new member of the acyl-CoA-binding protein family.

Project description:The X-ray structure of the tetragonal form of apo acyl-CoA-binding protein (ACBP) from the Harderian gland of the South American armadillo Chaetophractus villosus has been solved. ACBP is a carrier for activated long-chain fatty acids and has been associated with many aspects of lipid metabolism. Its secondary structure is highly similar to that of the corresponding form of bovine ACBP and exhibits the unique flattened alpha-helical bundle (up-down-down-up) motif reported for animal, yeast and insect ACBPs. Conformational differences are located in loops and turns, although these structural differences do not suffice to account for features that could be related to the unusual biochemistry and lipid metabolism of the Harderian gland.

| S-EPMC2225200 | biostudies-literature

Synthesis, structure elucidation, and antifungal potential of certain new benzodioxole-imidazole molecular hybrids bearing ester functionalities.

Project description:BackgroundThe incidence of fungal infections is a growing serious global health burden. There is an urgent medical demand to acquire new antifungal drug-like compounds having azole nuclei to get rid of the drawbacks of the currently available azole antifungal agents.MethodsThe target compounds 5a-r were synthesized in a four-step reaction sequence using the appropriate acetophenone derivative as a starting material. The antifungal potential of the title compounds was assessed using DIZ and MIC assays according to the reported standard procedures.ResultsThe newly synthesized oximino esters 5a-r were identified with the aid of various spectroscopic approaches. Their assigned chemical structures were confirmed via single-crystal X-ray structure of compound 5o. The molecular structure of compound 5o was crystallized in the triclinic, P-1, a=9.898 (3) Å, b=10.433 (3) Å, c=11.677 (4) Å, α =86.886 (6)°, β =87.071 (7)°, γ =64.385 (6)°, V=1,085.2 (6) Å3, Z=2. The synthesized compounds 5a-r were in vitro evaluated for antifungal potential against four fungal strains. Compounds 5l and 5m bearing a trifluoromethylphenyl moiety showed the best anti-Candida albicans activity with minimum inhibitory concentration (MIC) value of 0.148 μmol/mL, while compound 5b displayed the best activity toward Candida tropicalis with MIC value of 0.289 μmol/mL. Compounds 5o and 5l were the most active congeners against Candida parapsilosis and Aspergillus niger, respectively.ConclusionSingle-crystal X-ray analysis of compound 5o confirmed without doubt the assigned chemical structures of the title compounds as well as confirmed the (E)-configuration of their oximino group. Compounds 5b, 5l, 5m, and 5o emerged as the most active compounds against the tested fungi and they could be considered as new antifungal lead candidates.

| S-EPMC6396673 | biostudies-literature

OAF: a new member of the BRICHOS family.

Project description:SummaryThe 10 known BRICHOS domain-containing proteins in humans have been linked to an unusually long list of pathologies, including cancer, obesity and two amyloid-like diseases. BRICHOS domains themselves have been described as intramolecular chaperones that act to prevent amyloid-like aggregation of their proteins' mature polypeptides. Using structural comparison of coevolution-based AlphaFold models and sequence conservation, we identified the Out at First (OAF) protein as a new member of the BRICHOS family in humans. OAF is an experimentally uncharacterized protein that has been proposed as a candidate biomarker for clinical management of coronavirus disease 2019 infections. Our analysis revealed how structural comparison of AlphaFold models can discover remote homology relationships and lead to a better understanding of BRICHOS domain molecular mechanism.Supplementary informationSupplementary data are available at Bioinformatics Advances online.

| S-EPMC9714404 | biostudies-literature

Structure Elucidation of Nigricanoside A Through Enantioselective Total Synthesis.

Project description:Nigricanoside A was isolated from green alga, and its dimethyl ester was found to display potent cytotoxicity. Its scarcity prevented a full structure elucidation, leaving total synthesis as the only means to determine its relative and absolute stereochemistry and to explore its biological activity. Here we assign the stereochemistry of the natural product through enantioselective total synthesis and provide initial studies of its cytotoxicity.

| S-EPMC4751885 | biostudies-literature

A New Member of the Metal-Porphyrin Frameworks Family: Structure, Physicochemical Properties, Hydrogen and Carbon Dioxide Adsorption.

Project description:A novel holmium-based porous metal-porphyrin framework, {(H3 O+ )[Ho(H2 TPPS)]- ⋅ 4H2 O}n (denoted as UPJS-17), was synthesised by hydrothermal reaction. Structural analysis reveals, that UPJS-17 has a three-dimensional open framework. The framework is negatively charged and the negative charge is compensated by hydronium cation. The compound showed no N2 adsorption but the Ar, CO2 and H2 . From the argon adsorption, the surface area of ~150 m2 g-1 was determined. Carbon dioxide adsorption was measured at various temperatures (0, 10, 20, 30 and 40 °C) and the compound showed the highest adsorption capacity (at 0 °C) of 7.0 wt % of CO2 . From the carbon dioxide adsorption isotherms the isosteric heat of 56,5 kJ mol-1 was determined. Hydrogen adsorption was studied at -196 °C with hydrogen uptake of 2.1 wt % at 1 bar.

| S-EPMC10853072 | biostudies-literature

6-Azahemiporphycene: a new member of the porphyrinoid family.

Project description:The reaction of 5,10,15-triarylcorrole with 4-amino-4H-1,2,4-triazole provides another example of corrole ring expansion to give the corresponding 6-azahemiporphycene, a novel porphyrin analogue. The facile oxidation of the corrole ring is a required step for the ring expansion and for this reason the reaction fails in the case of corroles bearing meso-phenyl groups carrying electron-withdrawing substituents. Steric requirements also limited the scope of the reaction, which is not successful in the case of 2,6-disubstituted meso-aryl corroles. The occurrence of an initial oxidation is further supported by formation of the 6-azahemiporphycene derivative when the reaction is carried out under the same conditions, using a 5- or a 10-isocorrole as starting material. (1)H NMR spectra and X-ray crystal characterization of 6-azahemiporphycene evidenced the presence of an intramolecular N-H...N hydrogen bond in the inner core of the macrocycle, while photophysical characterization confirmed the aromatic character of the novel macrocycle, showing an intense Soret-like band around 410 nm in the absorption spectrum. The fluorescence emission is very modest, and 6-azahemiporphycene showed higher photostability than the corresponding corrole species. Different metal complexes of 6-azahemiporphycene were prepared following synthetic protocols usually exploited for the preparation of metalloporphyrins, demonstrating good coordination properties for the macrocycle. Both the free-base and metal derivatives were characterized by cyclic voltammetry and spectroelectrochemistry in dichloromethane and benzonitrile. To further detail the behavior of this novel macrocycle, density functional theory (DFT) calculations were carried out on the basic structure of 6-azahemiporphycene with the aim of assessing aromaticity and tautomerism, as well as calculating its stability with respect to the 5-aza isomer.

| S-EPMC2793671 | biostudies-literature

Polymerized Luteolin Nanoparticles: Synthesis, Structure Elucidation, and Anti-Inflammatory Activity.

Project description:Luteolin is an anti-inflammatory flavonoid commonly found in many edible plants. The compound is popularly consumed as a supplement regardless of its poor water solubility (27.8 μg/mL at 25 °C) and low bioavailability. Here, mild one-pot polymerization of luteolin into water-dispersible nanospheres, with an average dry size of 234.8 ± 101.6 nm, an aqueous size distribution of 379.1 ± 220.5 nm (PDI = 0.338), an average ζ-potential of -36.2 ± 0.2 mV, and an 89.3 ± 4.8% yield, is described. The nanospheres consist of polymerized luteolin (polyluteolin) with a weight-average molecular mass of around 410000 Da. The chemical structure of polyluteolin is identified through 1H-1H correlated spectroscopy (COSY), 1H-13C heteronuclear single-quantum coherence (HSQC), and 1H-13C heteronuclear multiple-bond correlation (HMBC) NMR spectroscopic analyses of the oligomers, and a polymerization mechanism is proposed. Unlike luteolin that showed both dose-dependent anti-inflammatory activity and cytotoxicity when tested in lipopolysaccharide-stimulated macrophages, the polyluteolin nanoparticles possess dose-dependent anti-inflammatory activity without causing cell death even at high concentrations.

| S-EPMC7860061 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data