New bio-nanocomposites based on iron oxides and polysaccharides applied to oxidation and alkylation reactions

• Daily Rodríguez-Padrón,
• Alina M. Balu,
• Antonio A. Romero and
• Rafael Luque

Beilstein J. Org. Chem. 2017, 13, 1982–1993, doi:10.3762/bjoc.13.194

• inexpensively produced by microbes, plants, and animals, and constitute a green alternative to synthetic polymers in the preparation of nanomaterials, in order to ameliorate environmental issues [34]. Therefore, one of the objectives of this work was to investigate the catalytic behavior of nanocomposites based

Enzymatic synthesis of glycosides: from natural O- and N-glycosides to rare C- and S-glycosides

• Jihen Ati,
• Pierre Lafite and
• Richard Daniellou

Beilstein J. Org. Chem. 2017, 13, 1857–1865, doi:10.3762/bjoc.13.180

• -glycosides have been described in literature [12][17][18]. Historically, glucosinolates have been the first identified S-glycosides for 50 years in cruciferous vegetables [19]. Along with the myrosinase GH enzyme, they are part of the “mustard bomb” system as a protective mechanism for plants against insect

• ]. More recently, BcGT1 from Bacillus subtilis was shown to efficiently catalyse the glucosylation of thiol-containing acceptors [32]. C-Glycosyltransferases For more than 50 years, C-glycosides have been identified in plants [33][34] as secondary metabolites. At least 5 families of aromatic aglycones

• have been reported to be C-glycosylated: flavones, xanthones, chromones, anthrones, and gallic acids. Several corresponding plant C-GT have been cloned, expressed and characterized, from several crops including maize [35], rice [36][37], wheat [36], buckwheat [38] and other plants such as Arabidopsis

18-Hydroxydolabella-3,7-diene synthase – a diterpene synthase from Chitinophaga pinensis

• Jeroen S. Dickschat,
• Jan Rinkel,
• Patrick Rabe,
• Arman Beyraghdar Kashkooli and
• Harro J. Bouwmeester

Beilstein J. Org. Chem. 2017, 13, 1770–1780, doi:10.3762/bjoc.13.171

• ) and the NSE triad NDXXSXX(R,K)(E,D), modified to a DTE triad in plants, for binding of the Mg2+ cofactor that forms a trinuclear (Mg2+)3 cluster to which the diphosphate portion of the substrate binds. Upon substrate binding the active site closes, resulting in hydrogen bonds between the substrate’s

• (−)-bornyl diphosphate synthases from the plants Salvia officinalis and Tanacetum vulgare forming a more polar product by the unusual termination via reattack of diphosphate [1], the trichodiene synthase from the fungus Trichothecium roseum [2], and pentalenene synthase from Streptomyces exfoliatus [3

• synthases in plants are targeted to the mitochondria [27], we decided to attempt the expression of HdS with mitochondrial targeting (HdS-mit). A construct without targeting signal (HdS; resulting in cytoplasmic localisation) and an empty vector were used as controls. A p19 construct [28] was co-infiltrated

A novel approach to oxoisoaporphine alkaloids via regioselective metalation of alkoxy isoquinolines

• Benedikt C. Melzer and
• Franz Bracher

Beilstein J. Org. Chem. 2017, 13, 1564–1571, doi:10.3762/bjoc.13.156

• bianfugecine (6) were isolated from Menispermum dauricum DC, among a few other plants [1][7][8]. A number of approaches to the oxoaporphine ring system has been published, typically involving the synthesis of 1-benzyl/1-benzoylisoquinoline intermediates, followed by cyclization under intramolecular biaryl

Glycoscience@Synchrotron: Synchrotron radiation applied to structural glycoscience

• Serge Pérez and
• Daniele de Sanctis

Beilstein J. Org. Chem. 2017, 13, 1145–1167, doi:10.3762/bjoc.13.114

• dynamics, plasticity of GTs and conformation changes that allow for substrate recognition and catalysis [37]. In plants, GTs are also involved in the biosynthesis of hemicellulose. Xyloglucan is one of the main hemicellulose components in the cell walls of dicots. Its biosynthesis involves different GTs

• to about 1,500. Interestingly, about 60% of them were obtained ligated to carbohydrates, which range from monosaccharides to 10 residue-long oligosaccharides. Lectins occur in plants, animals, algae, bacteria, fungi and yeasts, and viruses. Their involvement in key biologically-important recognition

• processes is well documented, as in the case of embryogenesis, fertilization, inflammation and metastasis. Lectins play a key role in parasite-symbiotic recognition in microbes and invertebrates of plants and vertebrates. The present role assigned to lectin lies in their ability to decipher sugar-encoded

From chemical metabolism to life: the origin of the genetic coding process

• Antoine Danchin

Beilstein J. Org. Chem. 2017, 13, 1119–1135, doi:10.3762/bjoc.13.111

Automating multistep flow synthesis: approach and challenges in integrating chemistry, machines and logic

• Chinmay A. Shukla and
• Amol A. Kulkarni

Beilstein J. Org. Chem. 2017, 13, 960–987, doi:10.3762/bjoc.13.97

• published work, patents, etc., by many folds. Automation is a powerful tool if used correctly, but can also be expensive if not utilized correctly [13]. Automation in chemical plants: The role of automation in chemical industries is to enhance the product quality, reduce the dependence on the availability

• industries have been experiencing growing demands for process automation services like hardware and standard software. Stephanopoulos has reviewed the process control approach in chemical plants in detail [52]. The process control system should be designed to achieve the control objectives which are

Use of costic acid, a natural extract from Dittrichia viscosa, for the control of Varroa destructor, a parasite of the European honey bee

• Kalliopi Sofou,
• Demosthenis Isaakidis,
• Apostolos Spyros,
• Anita Büttner,
• Athanassios Giannis and
• Haralambos E. Katerinopoulos

Beilstein J. Org. Chem. 2017, 13, 952–959, doi:10.3762/bjoc.13.96

• . It has been previously isolated from D. viscosa and its structure was confirmed via NMR analysis [36][37][38]. Moreover, D. viscosa is not the only species containing costic acid as a metabolite. It has been reported in the literature as a component in other plants such as Nectandra cissiflora, Nees

Opportunities and challenges for the sustainable production of structurally complex diterpenoids in recombinant microbial systems

• Katarina Kemper,
• Max Hirte,
• Markus Reinbold,
• Monika Fuchs and
• Thomas Brück

Beilstein J. Org. Chem. 2017, 13, 845–854, doi:10.3762/bjoc.13.85

• largest and most structurally diverse group of natural products. They are ubiquitous in bacteria, plants, animals and fungi, conducting several biological functions such as cell wall components or defense mechanisms. Industrial applications entail among others pharmaceuticals, food additives, vitamins

• isoprenoid titers in plants may be low in dependence to seasonal [9] or circadian expression [10]. On the other hand for some members simply the number of available plants may be limited like the pacific yew Taxus brevifolia from which paclitaxel was first extracted [11]. The chemical synthesis can be an

• plant diterpenes in well-established recombinant hosts, such as Escherichia coli [21][22][23]. Recent developments in this field will be reviewed in this work. Review Biosynthesis of diterpenes and transfer to heterologous production system Integration of biosynthetic gene clusters from plants into a

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

• Joyce Azzi,
• Pierre-Edouard Danjou,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2017, 13, 835–844, doi:10.3762/bjoc.13.84

• (Ner, 3,7,11-trimethyl-1,6,10-dodecatrien-3-ol), an acyclic sesquiterpene obtained from fresh flowers of bitter orange and found in many other plants [1], is extensively used in perfumery. It was also approved by the U.S. Food and Drug Administration as a food flavoring agent and included by the

Nucleophilic and electrophilic cyclization of N-alkyne-substituted pyrrole derivatives: Synthesis of pyrrolopyrazinone, pyrrolotriazinone, and pyrrolooxazinone moieties

• Işıl Yenice,
• Sinan Basceken and
• Metin Balci

Beilstein J. Org. Chem. 2017, 13, 825–834, doi:10.3762/bjoc.13.83

• (Figure 1) [7][8]. Triazinone heterocycles are essential in organic synthesis regarding their herbicide, anticancer, antimicrobial, and antimetastatic activities. Metamitron (3) and metribuzin (4), 1,2,4-triazinone herbicides having an amino group, are absorbed by the roots of plants and inhibit

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• isoxazole derivative, namely 3,5-difluorophenyl-[3-methyl-4-(methylsulfonyl)isoxazol-5-yl]methanone, was recently reported as an inducer of nitric oxide producing elicitor in plants [16][17]. Nitric oxide (NO), which has been demonstrated to be a major gasotransmitter in mammals, is also involved in the

• reactive oxygen species (ROS) production in plant tissues. Usually, NO and ROS, such as O2−, OH· and H2O2, together are required to induce the activation of various defense-related enzymes in plants [55]. Plant cells contain oxygen radical detoxifying enzymes and nonenzymatic antioxidants which have an

• generation in plant tissues and could activate various defense mechanisms in plants. Further research is in progress to assess the in planta mechanism of NO generation by these compounds. Synthetic route to 3,5-disubstituted isoxazoles. Reported 3,5-disubstituted isoxazoles. Supporting Information

Solid-phase enrichment and analysis of electrophilic natural products

• Frank Wesche,
• Yue He and
• Helge B. Bode

Beilstein J. Org. Chem. 2017, 13, 405–409, doi:10.3762/bjoc.13.43

• also be applied to extracts of other bacteria, fungi and plants and can give at least hints on new electrophilic natural products, where their reactivity against azide might also reflect their biological activity. (A) HPLC–MS base peak chromatograms of a crude XAD extract of P. luminescens TT01 and

Diels–Alder reactions of myrcene using intensified continuous-flow reactors

• Christian H. Hornung,
• Miguel Á. Álvarez-Diéguez,
• Thomas M. Kohl and
• John Tsanaktsidis

Beilstein J. Org. Chem. 2017, 13, 120–126, doi:10.3762/bjoc.13.15

• referred to in the following only as “myrcene” (1), see Scheme 1, vide infra). It can be found in significant quantities (up to 39%) in the essential oils of several plants, such as wild thyme [4], ylang-ylang [5], bay leaf [6], juniper berries [7], lemongrass [8], or parsley [9], and in smaller

First DMAP-mediated direct conversion of Morita–Baylis–Hillman alcohols into γ-ketoallylphosphonates: Synthesis of γ-aminoallylphosphonates

• Marwa Ayadi,
• Haitham Elleuch,
• Emmanuel Vrancken and
• Farhat Rezgui

Beilstein J. Org. Chem. 2016, 12, 2906–2915, doi:10.3762/bjoc.12.290

• biological potentials. Aminophosphonates and their derivatives [22][23][24][25][26] are thus recognized as promising compounds and a new class of drugs that are widely used in a variety of commercial applications. Indeed, they are known to influence various biochemical processes in plants, modifying or

O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside

• Roman Sommer,
• Dirk Hauck,
• Annabelle Varrot,
• Anne Imberty,
• Markus Künzler and
• Alexander Titz

Beilstein J. Org. Chem. 2016, 12, 2828–2833, doi:10.3762/bjoc.12.282

• -methylated carbohydrate ligands was demonstrated (e.g., 2, Figure 1). O-Methylation of carbohydrates is a rare modification, but widespread in nature as it has been observed in bacteria, protozoa, animals and plants but not in mammals [29][30]. Besides fungal and animal tectonins that recognize O-methylated

Interactions between cyclodextrins and cellular components: Towards greener medical applications?

• Loïc Leclercq

Beilstein J. Org. Chem. 2016, 12, 2644–2662, doi:10.3762/bjoc.12.261

• are, with proteins and lipids, essential constituents of living organisms because they are key biological intermediates for energy storage. In autotrophs, such as plants, sugars are converted into starch whereas for heterotrophic organisms, such as animals, they are stored as glycogen. However

• , polysaccharides serve also as structural components: cellulose for plants and chitin for arthropods. Moreover, saccharides and their derivatives play key roles in the immune system, fertilization, blood clotting, information transfer, etc. For instance, the 5-carbon monosaccharide ribose forms the backbone of the

A detailed view on 1,8-cineol biosynthesis by Streptomyces clavuligerus

• Jan Rinkel,
• Patrick Rabe,
• Laura zur Horst and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 2317–2324, doi:10.3762/bjoc.12.225

• complexity is reached within the largest, the terpenoids. An estimated number of 75,000 different compounds are known from all kinds of organisms including plants [1], bacteria [2][3][4][5], fungi [6] and, as recently shown, even social amoebae [7]. These molecules are all made from only a handful of linear

• conserved motifs including the aspartate-rich motif (DDXXD) and the NSE triad (ND(L,I,V)XSXXXE, modified in plants to a DTE triad: DD(L,I,V)XTXXXE) [8]. Their substrates bind with the diphosphate portion to the (Mg2+)3 cluster and via hydrogen bridges to a highly conserved arginine (diphosphate sensor) and

Robust C–C bonded porous networks with chemically designed functionalities for improved CO₂ capture from flue gas

• Damien Thirion,
• Joo S. Lee,
• Ercan Özdemir and
• Cafer T. Yavuz

Beilstein J. Org. Chem. 2016, 12, 2274–2279, doi:10.3762/bjoc.12.220

• high regeneration energy and raises the overall cost of the carbon capture operations [12][25]. Dry CO2 uptake is not always meaningful, especially with amine functionalities, as flue gas from power plants contains moisture [26]. When binding to CO2, amines go through either carbamate or carbamic acid

New furoisocoumarins and isocoumarins from the mangrove endophytic fungus Aspergillus sp. 085242

• Ze’en Xiao,
• Senhua Chen,
• Runlin Cai,
• Shao’e Lin,
• Kui Hong and
• Zhigang She

Beilstein J. Org. Chem. 2016, 12, 2077–2085, doi:10.3762/bjoc.12.196

• features and interesting biological activities. They have been widely isolated from fungi, lichens, bacteria, plants, and insects [1][2]. Furoisocoumarins combining a furan ring and an isocoumarin moiety are divided into two subclasses depending on their fusion type: linear furo[2,3-g]isocoumarins and

Mechanistic investigations on six bacterial terpene cyclases

• Patrick Rabe,
• Thomas Schmitz and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2016, 12, 1839–1850, doi:10.3762/bjoc.12.173

• interesting molecular properties. Particularly obvious is their often characteristic aroma that contributes to the typical flavour of many essential oils from plants. This is exemplified by the monoterpene α-pinene that occurs in form of both enantiomers in pine trees, while (R)-(+)-limonene is found in

• WP_003956090) [19], but the two enzymes show only a sequence homology of 32% and are phylogenetically distant. The (−)-enantiomer is known from plants including Taiwania cryptomerioides ([α]D23 = −102.9 (c 1.0, CHCl3)) [42], while the (+)-enantiomer has also been isolated from the liverwort Scapania undulata

• strict stereochemical course for the FPP cyclisation, as is reported for most, but not all other terpene cyclases that were investigated for this aspect. It is interesting to note that the bacterial sesquiterpenes identified in this study are in most cases the opposite enantiomers as known from plants

Cross-linked cyclodextrin-based material for treatment of metals and organic substances present in industrial discharge waters

• Élise Euvrard,
• Nadia Morin-Crini,
• Coline Druart,
• Justine Bugnet,
• Bernard Martel,
• Cesare Cosentino,
• Virginie Moutarlier and
• Grégorio Crini

Beilstein J. Org. Chem. 2016, 12, 1826–1838, doi:10.3762/bjoc.12.172

• their own treatment plants, generally physicochemical decontamination steps, the DWs still contain non-negligible amounts of pollutants. Among them, metals (in particular chromium, nickel and zinc) are commonly found at concentrations in the range of milligrams per liter, and organic molecules, such as

Rearrangements of organic peroxides and related processes

• Ivan A. Yaremenko,
• Vera A. Vil’,
• Dmitry V. Demchuk and
• Alexander O. Terent’ev

Beilstein J. Org. Chem. 2016, 12, 1647–1748, doi:10.3762/bjoc.12.162

Organic chemistry meets polymers, nanoscience, therapeutics and diagnostics

• Vincent M. Rotello

Beilstein J. Org. Chem. 2016, 12, 1638–1646, doi:10.3762/bjoc.12.161

• stuff found in cells [68]. This was the start of a collaboration that continues to this day, where we have used laser desorption ionization (LDI) to characterize ligands on particles [69][70], supramolecular chemistry in cells [71], track NPs in fish [72] and plants [73], and to image NPs in animal

Mutagenic activity of quaternary ammonium salt derivatives of carbohydrates

• Barbara Dmochowska,
• Karol Sikora,
• Anna Woziwodzka,
• Jacek Piosik and
• Beata Podgórska

Beilstein J. Org. Chem. 2016, 12, 1434–1439, doi:10.3762/bjoc.12.138

• mutagenicity test; quaternary ammonium salt; Introduction Carbohydrates and alditols occur broadly in nature and possess many biological functions essential to living organisms. Sugars not only contribute as energetic substances, but also serve as building materials for fungi, microbes, plants, and animals