Beilstein Journal of Organic Chemistry This is an RSS file. You can use it to subscribe to this data in your favourite RSS reader or to display this data on your own website or blog.

Synthesis of meso-pyrrole-substituted corroles by condensation of 1,9-diformyldipyrromethanes with pyrrole
Abstract A copper triflate-mediated approach to access copper complexes of pyrrole-substituted corroles from the reaction of 1,9-diformyldipyrromethanes and an excess amount of pyrrole is presented for the first time. This procedure is a simple and efficient way for the preparation of corroles with a polymerizable substituent on meso-positions. Beilstein J. Org. Chem. 2022, 18, 1403–1409. doi:10.3762/bjoc.18.145 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - October 6, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: corrole dipyrromethane macrocycles metal triflates pyrrole Full Research Paper Source Type: research

Characterization of a new fusicoccane-type diterpene synthase and an associated P450 enzyme
Abstract Fusicoccane-type terpenoids are a subgroup of diterpenoids featured with a unique 5-8-5 ring system. They are widely distributed in nature and possess a variety of biological activities. Up to date, only five fusicoccane-type diterpene synthases have been identified. Here, we identify a two-gene biosynthetic gene cluster containing a new fusicoccane-type diterpene synthase gene tadA and an associated cytochrome P450 gene tadB from Talaromyces wortmannii ATCC 26942. Heterologous expression reveals that TadA catalyzes the formation of a new fusicoccane-type diterpene talaro-7,13-diene. D2O isotope labeling combined ...
Source: Beilstein Journal of Organic Chemistry - October 5, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cytochrome P450 enzyme diterpene synthase gene cluster genome mining site-directed mutagenesis Full Research Paper Source Type: research

Preparation of an advanced intermediate for the synthesis of leustroducsins and phoslactomycins by heterocycloaddition
Abstract A convergent strategy for the synthesis of leustroducsins and phoslactomycins has been designed, relying on the synthesis and the coupling of three main fragments. The central fragment was synthesized via a regio-and stereoselective nitroso Diels–Alder reaction with an enol phosphate, followed by reductive cleavage of the phosphate to the ketone 11b. Coupling studies of this fragment with the lactone fragment was accomplished in a stereoselective fashion through a vinyllithium intermediate. An advanced synthetic intermediate was then obtained after functional group transformation. Beilstein J. Org. Chem. 20...
Source: Beilstein Journal of Organic Chemistry - October 4, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cycloaddition organolithium stereoselective total synthesis Full Research Paper Source Type: research

Synthesis of C6-modified mannose 1-phosphates and evaluation of derived sugar nucleotides against GDP-mannose dehydrogenase
We present herein the design and chemoenzymatic synthesis of sugar nucleotide tools to probe a critical enzyme within alginate biosynthesis, GDP-mannose dehydrogenase (GMD). We first synthesise C6-modified glycosyl 1-phosphates, incorporating 6-amino, 6-chloro and 6-sulfhydryl groups, followed by their evaluation as substrates for enzymatic pyrophosphorylative coupling. The development of this methodology enables access to GDP 6-chloro-6-deoxy-ᴅ-mannose and its evaluation against GMD. Beilstein J. Org. Chem. 2022, 18, 1379–1384. doi:10.3762/bjoc.18.142 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - September 30, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: alginate chemical probe enzymatic synthesis GDP-mannose dehydrogenase sugar nucleotide Letter Source Type: research

On drug discovery against infectious diseases and academic medicinal chemistry contributions
In conclusion, this text is an actual plea illustrating that, in many countries, academic research in medicinal chemistry should be more funded, especially in the therapeutic area neglected by the industry. At the least, such funds would provide the intensive to secure series of hopefully relevant chemical entities which appears to often lack when considering the results of academic as well as industrial screening campaigns. Beilstein J. Org. Chem. 2022, 18, 1355–1378. doi:10.3762/bjoc.18.141 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - September 29, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: antibacterials frequent hitters hit to lead chemical library medicinal chemistry virtual docking Perspective Source Type: research

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies
Abstract A simple method for the preparation of β-cyclodextrin derivatives containing covalently bonded aldehydes via an imine bond was developed and used to prepare a series of derivatives from 6I-amino-6I-deoxy-β-cyclodextrin and the following volatile aldehydes – cinnamaldehyde, cyclamen aldehyde, lilial, benzaldehyde, anisaldehyde, vanillin, hexanal, heptanal, citral, and 5-methylfurfural. Subsequently, the rate of release of the volatile compound from selected pro-fragrances, as a function of the environment (solvent, pH), was studied by 1H NMR spectroscopy (for benzaldehyde) and static headspace-gas c...
Source: Beilstein Journal of Organic Chemistry - September 28, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: aldehyde controlled release cyclodextrin imine kinetics pro-fragrance Schiff base Full Research Paper Source Type: research

Synthesis and electrochemical properties of 3,4,5-tris(chlorophenyl)-1,2-diphosphaferrocenes
Abstract A novel representative of sodium 3,4,5-triaryl-1,2-diphosphacyclopentadienide containing a chloro substituent in the meta-position of the aryl groups was obtained with a high yield based on the reaction of tributyl(1,2,3-triarylcyclopropenyl)phosphonium bromide and sodium polyphosphides. Further reaction of sodium 3,4,5-tris(3-chlorophenyl)-1,2-diphosphacyclopentadienide with [FeCp(η6-C6H5CH3)][PF6] complex gives a new 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene. The electrochemical properties of 3,4,5-tris(3-chlorophenyl)-1,2-diphosphaferrocene were studied and compared to 3,4,5-tris(4-chlorophenyl)-1,...
Source: Beilstein Journal of Organic Chemistry - September 27, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: cyclopropenyl bromide electrochemical properties phosphacyclopentadienide anion phosphaferrocene phosphonium salt phosphorus heterocycle Full Research Paper Source Type: research

B – N/B – H Transborylation: borane-catalysed nitrile hydroboration
Abstract The reduction of nitriles to primary amines is a useful transformation in organic synthesis, however, it often relies upon stoichiometric reagents or transition-metal catalysis. Herein, a borane-catalysed hydroboration of nitriles to give primary amines is reported. Good yields (48–95%) and chemoselectivity (e.g., ester, nitro, sulfone) were observed. DFT calculations and mechanistic studies support the proposal of a double B–N/B–H transborylation mechanism. Beilstein J. Org. Chem. 2022, 18, 1332–1337. doi:10.3762/bjoc.18.138 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - September 26, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: boron catalysis hydroboration nitrile transborylation Letter Source Type: research

Computational model predicts protein binding sites of a luminescent ligand equipped with guanidiniocarbonyl-pyrrole groups
Abstract The 14-3-3 protein family, one of the first discovered phosphoserine/phosphothreonine binding proteins, has attracted interest not only because of its important role in the cell regulatory processes but also due to its enormous number of interactions with other proteins. Here, we use a computational approach to predict the binding sites of the designed hybrid compound featuring aggregation-induced emission luminophores as a potential supramolecular ligand for 14-3-3ζ in the presence and absence of C-Raf peptides. Our results suggest that the area above and below the central pore of the dimeric 14-3-3ζ pr...
Source: Beilstein Journal of Organic Chemistry - September 23, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: AIE luminophores fluorescence emission guanidiniocarbonyl-pyrrole ligand binding 14-3-3 protein Full Research Paper Source Type: research

Ionic multiresonant thermally activated delayed fluorescence emitters for light emitting electrochemical cells
Abstract We designed and synthesized two new ionic thermally activated delayed fluorescent (TADF) emitters that are charged analogues of a known multiresonant TADF (MR-TADF) compound, DiKTa. The emission of the charged derivatives is red-shifted compared to the parent compound. For instance, DiKTa-OBuIm emits in the green (λPL = 499 nm, 1 wt % in mCP) while DiKTa-DPA-OBuIm emits in the red (λPL = 577 nm, 1 wt % in mCP). In 1 wt % mCP films, both emitters showed good photoluminescence quantum yields of 71% and 61%, and delayed lifetimes of 316.6 μs and 241.7 μs, respectively, for DiKTa-OBuIm and DiKTa-DP...
Source: Beilstein Journal of Organic Chemistry - September 22, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: electroluminescence light-emitting electrochemical cells multiresonance purely organic emitters thermally activated delayed fluorescence Full Research Paper Source Type: research

Cytochrome P450 monooxygenase-mediated tailoring of triterpenoids and steroids in plants
We describe the phylogenetic distribution of triterpenoid- and steroid-modifying CYPs across the plant CYPome, present a structure-based summary of their reactions, and highlight recent examples of particular interest to the field. Our review therefore provides a comprehensive up-to-date picture of CYPs involved in the biosynthesis of triterpenoids and steroids in plants as a starting point for future research. Beilstein J. Org. Chem. 2022, 18, 1289–1310. doi:10.3762/bjoc.18.135 (Source: Beilstein Journal of Organic Chemistry)
Source: Beilstein Journal of Organic Chemistry - September 21, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: biosynthesis CYPs cytochrome P450 monooxygenases plants steroid sterol triterpene triterpenoid Review Source Type: research

Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions
Abstract Polyphosphate kinases (PPKs) have become popular biocatalysts for nucleotide 5'-triphosphate (NTP) synthesis and regeneration. Two unrelated families are described: PPK1 and PPK2. They are structurally unrelated and use different catalytic mechanisms. PPK1 enzymes prefer the usage of adenosine 5'-triphosphate (ATP) for polyphosphate (polyP) synthesis while PPK2 enzymes favour the reverse reaction. With the emerging use of PPK enzymes in biosynthesis, a deeper understanding of the enzymes and their thermodynamic reaction course is of need, especially in comparison to other kinases. Here, we tested four PPKs...
Source: Beilstein Journal of Organic Chemistry - September 20, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: ATP regeneration biocatalyst ePC-SAFT polyp PPK Full Research Paper Source Type: research

Enantioselective total synthesis of putative dihydrorosefuran, a monoterpene with an unique 2,5-dihydrofuran structure
Abstract An original synthesis of the structure of dihydrorosefuran, a compound allegedly identified in Artemisia pallens and Tagetes mendocina, has been developed. The key steps in the five-step 36% overall yield synthesis are a CpTiIIICl2 mediated Barbier-type allenylation of a linear aldehyde and the formation of a 2,5-dihydrofuran scaffold through a Ag(I)-mediated cyclization. Neither of the reported spectral data for dihydrorosefuran match those of the synthetic product, suggesting that the isolated compound from Tagetes mendocina is in fact the natural product rosiridol, while the real structure of the product from A...
Source: Beilstein Journal of Organic Chemistry - September 19, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: Ag(I) cyclization allenylation CpTiCl2 2,5-dihydrofurans monoterpenes Full Research Paper Source Type: research

Ferrocenoyl-adenines: substituent effects on regioselective acylation
Abstract A series of N6-substituted adenine–ferrocene conjugates was prepared and the reaction mechanism underlying the synthesis was explored. The SN2-like reaction between ferrocenoyl chloride and adenine anions is a regioselective process in which the product ratio (N7/N9-ferrocenoyl isomers) is governed by the steric property of the substituent at the N6-position. Steric effects were evaluated by using Charton (empirical) and Sterimol (computational) parameters. The bulky substituents may shield the proximal N7 region of space, which prevents the approach of an electrophile towards the N7 atom. As a consequence, ...
Source: Beilstein Journal of Organic Chemistry - September 19, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: DFT ferrocene nucleophilicity purine steric effect Full Research Paper Source Type: research

Modular synthesis of 2-furyl carbinols from 3-benzyldimethylsilylfurfural platforms relying on oxygen-assisted C – Si bond functionalization
Abstract 3-Silylated furfurals, readily prepared in three steps from biomass-derived furfural and 5-methylfurfural, are converted into 3-silylated 2-furyl carbinols upon condensation with organomagnesium or organolithium reagents. The hydroxy unit of the carbinol adducts can be exploited to promote C3(sp2)–Si bond functionalization through intramolecular activation. Two approaches were contemplated for this purpose. Activation by alkoxides of the C3–SiEt3 or C3–SiMe2t-Bu bonds was ineffective. Conversely, treatment of the C3-benzyldimethylsilyl-appended derivatives with tetrabutylammonium fluoride led to ...
Source: Beilstein Journal of Organic Chemistry - September 16, 2022 Category: Chemistry Authors: Beilstein Journal of Organic Chemistry - Syndicated Feeds Tags: biomass copper cyclic siloxanes 2-furyl carbinols silicon Full Research Paper Source Type: research