Metal-free visible-light-enabled vicinal trifluoromethyl dithiolation of unactivated alkenes

• Xiaojuan Li,
• Qiang Zhang,
• Weigang Zhang,
• Jinzhu Ma,
• Yi Wang and
• Yi Pan

Beilstein J. Org. Chem. 2021, 17, 551–557, doi:10.3762/bjoc.17.49

• corresponding SCF3 adducts. In addition, boldenone- and ᴅ-glucose-derived terminal alkenes were compatible with the conditions affording the corresponding products 5l and 5m in moderate to good yields. To gain insight into the reaction mechanism, control experiments were conducted under the standard conditions

Identification of volatiles from six marine Celeribacter strains

• Anuj Kumar Chhalodia,
• Jan Rinkel,
• Dorota Konvalinkova,
• Jörn Petersen and
• Jeroen S. Dickschat

Beilstein J. Org. Chem. 2021, 17, 420–430, doi:10.3762/bjoc.17.38

• incorporation was observed for the other two sulfur atoms of 41 prompted us to further investigate the biosynthetic origin of the benzothiazol-2-ylsulfanyl portion of 41 to establish its natural origin. Several feeding experiments with central primary metabolites including (13C6)glucose, (13C5)ribose and

Regioselective chemoenzymatic syntheses of ferulate conjugates as chromogenic substrates for feruloyl esterases

• Olga Gherbovet,
• Fernando Ferreira,
• Apolline Clément,
• Mélanie Ragon,
• Julien Durand,
• Sophie Bozonnet,
• Michael J. O'Donohue and
• Régis Fauré

Beilstein J. Org. Chem. 2021, 17, 325–333, doi:10.3762/bjoc.17.30

• /L ammonium chloride, 20 mL/L oleic acid, 10 g/L ᴅ-glucose, 2 g/L casamino acid, and 15 g/L bacto agar in 100 mM citrate–phosphate buffer at pH 5). The petri dishes were incubated for 48 h at 30 °C and then overlayered with a preparation of 1% (w/v) molten top agar containing the chromogenic

Direct synthesis of anomeric tetrazolyl iminosugars from sugar-derived lactams

• Michał M. Więcław and
• Bartłomiej Furman

Beilstein J. Org. Chem. 2021, 17, 115–123, doi:10.3762/bjoc.17.12

• iminosugar derivatives may be less obvious. Several pharmaceuticals are based on this scaffold including the glucose-derived nojirimycin, an antibiotic and glycosidase inhibitor [26] and 1-deoxygalactonojirimycin, known under the trade name Galafold®, which is utilized for the treatment of the Fabry disease

• standard Ugi–azide reaction conditions [35][36][37][38][39] in a one-pot, tandem process. Subjecting glucose-derived lactam 1 to such a procedure gave the desired product in good yield, but with virtually no diastereoselectivity, as shown in Scheme 2. Optimization and scope An initial optimization study

• conformer. Therefore, once the ground conformer of the oxocarbenium ion is established, this logic may be used to predict the reaction’s stereochemistry. The same principle may be successfully applied to reactions of iminium cations. We have previously shown that in the case of glucose- and galactose

Semiautomated glycoproteomics data analysis workflow for maximized glycopeptide identification and reliable quantification

• Steffen Lippold,
• Arnoud H. de Ru,
• Jan Nouta,
• Peter A. van Veelen,
• Magnus Palmblad,
• Manfred Wuhrer and
• Noortje de Haan

Beilstein J. Org. Chem. 2020, 16, 3038–3051, doi:10.3762/bjoc.16.253

• -glycans are attached to Ser or Thr. Glycan compositions can range from monosaccharides (e.g., Tn antigen for O-glycans [1]) to large polysaccharides (e.g., N-glycans of recombinant human erythropoietin [2]). The most common building blocks of human protein glycans are hexoses (glucose, galactose, and

Secondary metabolites of Bacillus subtilis impact the assembly of soil-derived semisynthetic bacterial communities

• Heiko T. Kiesewalter,
• Carlos N. Lozano-Andrade,
• Mikael L. Strube and
• Ákos T. Kovács

Beilstein J. Org. Chem. 2020, 16, 2983–2998, doi:10.3762/bjoc.16.248

• g⋅L−1 dipotassium hydrogen phosphate, and 2.5 g⋅L−1 glucose. Semisynthetic mock community assay Semisynthetic soil communities were obtained from the soil of sampling site P5 (55.788800, 12.558300) [51][64]. 1 g soil was mixed in a 1:9 ratio with a 0.9% saline solution, vortexed on a rotary shaker

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

Beilstein J. Org. Chem. 2020, 16, 2971–2982, doi:10.3762/bjoc.16.247

• serum albumin. Other biomolecules such as adenosine, adenosine monophosphate, adenosine triphosphate, phosphate, pyrophosphate, glucose, heparin, hyaluronic acid and chondroitin sulfate, and amino acids containing two carboxylates (glutamic acid and aspartic acid) have not increased the fluorescence

• biological analytes including such as adenosine, adenosine monophosphate (AMP), adenosine triphosphates (ATP), phosphate (Pi), pyrophosphate (PPi), ct-DNA, glucose, bovine serum albumin (BSA), glutamic acid and aspartic acid. They are also selective over the similar biological analytes hyaluronic acid or

Ultrasound-assisted Strecker synthesis of novel 2-(hetero)aryl-2-(arylamino)acetonitrile derivatives

• Emese Gal,
• Luiza Gaina,
• Hermina Petkes,
• Alexandra Pop,
• Castelia Cristea,
• Gabriel Barta,
• Dan Cristian Vodnar and
• Luminiţa Silaghi-Dumitrescu

Beilstein J. Org. Chem. 2020, 16, 2929–2936, doi:10.3762/bjoc.16.242

• activity. The viability of Salmonella typhimurium TA98 and TA 100, respectively, was assessed by exposing the histidine dependent bacteria to compound 2c, 2i, and 2l, respectively, directly on minimal glucose agar plates in the presence or absence of the metabolic activation system S9. The number of

Fluorine effect in nucleophilic fluorination at C4 of 1,6-anhydro-2,3-dideoxy-2,3-difluoro-β-D-hexopyranose

• Danny Lainé,
• Vincent Denavit,
• Olivier Lessard,
• Laurie Carrier,
• Charles-Émile Fecteau,
• Paul A. Johnson and
• Denis Giguère

Beilstein J. Org. Chem. 2020, 16, 2880–2887, doi:10.3762/bjoc.16.237

• (retention of configuration) with a 39% yield along with glucose 11 (inversion of configuration) in 31% yield (Table 1, entry 2) [20][30]. Moreover, the use of the talose analogue 4 generated exclusively the product with retention of configuration 12. This result was surprising since the only difference with

• alditol analogues was achieved. The strategy described herein will allowed us to achieve the synthesis of other polyfluorinated hexitol analogues in order to explore their physical properties. Previously described synthesis of 2,3,4-trifluorinated analogues of galactose 6, glucose 7, mannose 8, and talose

Easy access to a carbohydrate-based template for stimuli-responsive surfactants

• Thomas Holmstrøm,
• Daniel Raydan and
• Christian Marcus Pedersen

Beilstein J. Org. Chem. 2020, 16, 2788–2794, doi:10.3762/bjoc.16.229

• for conformational switches but have, to our knowledge, never been used as stimuli-responsive surfactants [13][14]. The compounds would have the benefit of being generally inexpensive due to the high production of glucose. However, going from glucose to a conformational switch often involves time

• and lipophilic groups at a late stage of the synthesis (Figure 1a). The synthesis is centered around the cheap and commercially available levoglucosan, a glucose derivative that can be produced directly from cellulose [19]. This building block seemed ideal for the synthesis of a stimuli-responsive

Encrypting messages with artificial bacterial receptors

• Pragati Kishore Prasad,
• Naama Lahav-Mankovski,
• Leila Motiei and
• David Margulies

Beilstein J. Org. Chem. 2020, 16, 2749–2756, doi:10.3762/bjoc.16.225

• -ODN-1 were incubated (50 μM each) with NiCl2·6H2O (2.5 mM) in Milli-Q water for 30 min. Meanwhile, the bacterial samples were collected by centrifugation at 6000g for 4 min. The pellets were washed twice with M9 medium (supplemented with 2% glucose) and resuspended in 99 μL of the medium to an OD600

Nocarimidazoles C and D, antimicrobial alkanoylimidazoles from a coral-derived actinomycete Kocuria sp.: application of ¹J_C,H coupling constants for the unequivocal determination of substituted imidazoles and stereochemical diversity of anteisoalkyl chains in microbial metabolites

• Md. Rokon Ul Karim,
• Enjuro Harunari,
• Amit Raj Sharma,
• Naoya Oku,
• Kazuaki Akasaka,
• Daisuke Urabe,
• Mada Triandala Sibero and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 2719–2727, doi:10.3762/bjoc.16.222

• production medium, which consists of 0.2% glucose, 2.5% soluble starch, 0.5% yeast extract, 0.5% polypeptone (Wako Pure Chemical Industries, Ltd.), 0.5% NZ-amine (Wako Pure Chemical Industries, Ltd.), 0.3% CaCO3, and 1% Diaion HP-20 (Mitsubishi Chemical Co.) in natural seawater (collected from Toyama Bay

A consensus-based and readable extension of Linear Code for Reaction Rules (LiCoRR)

• Benjamin P. Kellman,
• Yujie Zhang,
• Emma Logomasini,
• Eric Meinhardt,
• Karla P. Godinez-Macias,
• Austin W. T. Chiang,
• James T. Sorrentino,
• Chenguang Liang,
• Bokan Bao,
• Yusen Zhou,
• Sachiko Akase,
• Isami Sogabe,
• Thukaa Kouka,
• Elizabeth A. Winzeler,
• Iain B. H. Wilson,
• Matthew P. Campbell,
• Sriram Neelamegham,
• Frederick J. Krambeck,
• Kiyoko F. Aoki-Kinoshita and
• Nathan E. Lewis

Beilstein J. Org. Chem. 2020, 16, 2645–2662, doi:10.3762/bjoc.16.215

• , “ G ” represents glucopyranose, the pyranose conformation of glucose, with ᴅ stereospecificity. Glucopyranose with ʟ stereospecificity is written as “ G’ ” (SRS1). Glucofuranose with ᴅ stereospecificity is written as “ G^ ” (SRS2), and glucofuranose with ʟ specificity is written as “ G~ ” (SRS3

• ). Similarly, galactofuranose, a common fungal monosaccharide, would be written “A^” Open form rule indicates that if the MS at the reducing end is open – a linear rather than cyclic MS, then the final character to the right of the string should be "o". For example, lactose, galactose β-linked to glucose would

• be written as AbG if the reducing end glucose is closed and AbGo if the glucose is open; the open "o" takes the place of the linkage in this context. If the glucose is phosphorylated, this structure would be written AbG[P]o. Modification rules specify a modification of a MS at certain positions (MR1

Water-soluble host–guest complexes between fullerenes and a sugar-functionalized tribenzotriquinacene assembling to microspheres

• Si-Yuan Liu,
• Xin-Rui Wang,
• Man-Ping Li,
• Wen-Rong Xu and
• Dietmar Kuck

Beilstein J. Org. Chem. 2020, 16, 2551–2561, doi:10.3762/bjoc.16.207

• Department of Chemistry, Center for Molecular Materials (CM2), Bielefeld University, 33615 Bielefeld, Germany 10.3762/bjoc.16.207 Abstract A sugar-functionalized water-soluble tribenzotriquinacene derivative bearing six glucose residues, TBTQ-(OG)6, was synthesized and its interaction with C60 and C70

• ]. The acetyl protons of the protected glucose residues appear as eight distinct resonances. The 13C NMR spectrum shows a similar splitting. The triazole carbons resonate at δ = 123.71 and δ = 123.69 ppm and at δ = 143.88 and δ = 143.79 ppm, indicating two sets of magnetically nonequivalent linkers. This

• sodium cations requires further studies. Despite the unusual mass spectrometric behavior of the compound, the combined spectroscopic evidence strongly supports the identity of TBTQ-(OAcG)6. After deprotection of the glucose units, the acetyl signals disappeared in the 1H and 13C NMR spectra of the target

Computational tools for drawing, building and displaying carbohydrates: a visual guide

• Kanhaya Lal,
• Rafael Bermeo and
• Serge Perez

Beilstein J. Org. Chem. 2020, 16, 2448–2468, doi:10.3762/bjoc.16.199

• a continuous development and evolution of the description of monosaccharides [2]. Glycans are puzzles to many chemists, and biologists as well as bioinformaticians. This complexity occurs at different levels (which makes it incremental). Amongst the most recognisable “sugars”, glucose is merely one

• glucose. And yet, monosaccharides are only the chemical units and the individual building blocks of much more complex molecules; the carbohydrates, also referred to as glycans. The glycan family can be grouped in the following categories: (i) oligosaccharides (comprising two to ten monosaccharides linked

• linkage as alpha or beta (or unknown) and to state the positions of the glycosyl acceptor and even donor. Cellulose and amylose are two glucose-based polysaccharides that differ only in the nature of their glycosidic bond, and yet they have entirely different shapes and so, biological roles. For the sake

Recent developments in enantioselective photocatalysis

• Callum Prentice,
• James Morrisson,
• Andrew D. Smith and
• Eli Zysman-Colman

Beilstein J. Org. Chem. 2020, 16, 2363–2441, doi:10.3762/bjoc.16.197

A proposed sustainability index for synthesis plans based on input provenance and output fate: application to academic and industrial synthesis plans for vanillin as a case study

• John Andraos

Beilstein J. Org. Chem. 2020, 16, 2346–2362, doi:10.3762/bjoc.16.196

• alphabetical order along with temperature and pressure conditions for each reaction step. Table 2 summarizes the same alphabetized list showing the plan codes, starting materials used, and type of chemical process employed. Four plans involved biofermentation from ᴅ-glucose, ferulic acid, or isoeugenol [26][27

• scales that are several orders of magnitude longer than organism time scales. (4) Lignosulfonic acid liquor and sawdust were considered renewable inputs since they ultimately originate from trees. Ferulic acid and ᴅ-glucose were considered renewable inputs since they originate from sugar beet biomass [47

• 145, 105, and 101, respectively. Plans p11 (Lampman synthesis from sawdust), p10 (Ji synthesis from guaiacol), p14 (Mexican group SFE), p9 (Hibbert synthesis from lignosulfonic acid liquor), p21 (Soxhlet extraction from ground vanilla beans), and p6 (Frost biofermentation from ᴅ-glucose) have the

Host–guest interaction of cucurbit[8]uril with oroxin A and its effect on the properties of oroxin A

• Zhishu Zeng,
• Jun Xie,
• Guangyan Luo,
• Zhu Tao and
• Qianjun Zhang

Beilstein J. Org. Chem. 2020, 16, 2332–2337, doi:10.3762/bjoc.16.194

• the entry into the cavity of Q[8]. The proton peaks of the glycosidic H and glucose were shifted downfield, indicating that they were located at the portal of Q[8]. However, when OA is present in excess, some of the proton peaks of the OA aglycon moved upfield, and some move downfield, indicating that

• ] formed a host–guest complex in a ratio of 1:1. The aglycone of OA entered the cavity of Q[8] and the glucose was located at the portal of Q[8], with a binding constant of 1.299 × 107 L·mol−1. The solubility of oroxin A was increased 22.47-fold when the concentration of the added Q[8] was 1.0 × 10−4 mol·L

The B & B approach: Ball-milling conjugation of dextran with phenylboronic acid (PBA)-functionalized BODIPY

• Patrizia Andreozzi,
• Lorenza Tamberi,
• Elisamaria Tasca,
• Gina Elena Giacomazzo,
• Marta Martinez,
• Mirko Severi,
• Marco Marradi,
• Stefano Cicchi,
• Sergio Moya,
• Giacomo Biagiotti and
• Barbara Richichi

Beilstein J. Org. Chem. 2020, 16, 2272–2281, doi:10.3762/bjoc.16.188

• excess of PBA (more than 60-fold excess of PBA to dextran, in a glucose/PBA 1:1 molar ratio reaction) was employed. However, the resulting dextran functionalization was low (1.6 PBA units out of 60 glucose units). In our studies we used PBA-BODIPY (1), a dye which proved to show excellent optical

• roughly equimolar amount of Dex and 1, in a glucose units/1 molar ratio of 60:1 (assuming an average molecular weight for Dex of 10 kDa). For the labeling in solution, Dex was dissolved in dry dimethyl sulfoxide (DMSO) and PBA-BODIPY (1) was added in roughly equimolar amounts (Scheme 1, route A). The

• compared to Dex. Therefore, mechanochemical reactions were carried out using a glucose units/1 molar ratio of 120:1 and 600:1. The conjugations yield was determined by measuring the absorption of the conjugates (λmax = 508–511 nm, Figure 2B and Supporting Information File 1, Figures S3 and S4), and

Clustering and curation of electropherograms: an efficient method for analyzing large cohorts of capillary electrophoresis glycomic profiles for bioprocessing operations

• Ian Walsh,
• Matthew S. F. Choo,
• Sim Lyn Chiin,
• Amelia Mak,
• Shi Jie Tay,
• Pauline M. Rudd,
• Yang Yuansheng,
• Andre Choo,
• Ho Ying Swan and
• Terry Nguyen-Khuong

Beilstein J. Org. Chem. 2020, 16, 2087–2099, doi:10.3762/bjoc.16.176

• , migration time is generally calculated by correlation with internal standards that bracket the time of elution of the glycans of interest [10]. This process is used to calculate a glucose unit (GU) which helps to align the datasets so that the GU of each glycan can be used to identify the glycan through

• based on a triple standard GU calculation [10][11] and database matching whilst the quantitation used HappyTools calibration and area calculation [14]. The GU calculation involved standardizing the migration time of the peaks by generating a ‘virtual’ glucose unit (GU) ladder calculated using the

• using dual pitch blade impellers stirring at 300 rpm. Different bioreactor operating conditions were evaluated. Triplicate experiments were performed for all operating conditions under study. In terms of the feeding strategy, 10% of EX-CELL Advanced CHO Feed 1 (with glucose) were added to all cultures

Syntheses of spliceostatins and thailanstatins: a review

• William A. Donaldson

Beilstein J. Org. Chem. 2020, 16, 1991–2006, doi:10.3762/bjoc.16.166

• FR901464 (1) from chiral pool precursors Kitahara’s group fashioned the C-1–C-6 tetrahydropyran fragment of FR901464 (1) from commercially available 2-deoxy-ᴅ-glucose. In the first-generation approach (66, Scheme 10) [8], a sequence of protection and oxidation steps generated the tetrahydropyrone 67 at

Three new O-isocrotonyl-3-hydroxybutyric acid congeners produced by a sea anemone-derived marine bacterium of the genus Vibrio

• Dandan Li,
• Enjuro Harunari,
• Tao Zhou,
• Naoya Oku and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1869–1874, doi:10.3762/bjoc.16.154

• adjusted to 7.6. After being fermented at 30 °C at 200 rpm for 2 days, 3 mL aliquots of the seed culture thus prepared were dispensed into 500 mL K-1 flasks, each containing 100 mL A16 production medium consisting of 2% glucose, 1% Pharmamedia, 0.5% CaCO3 and 1% Diaion HP-20 in natural seawater. After

• . Antibacterial assay The antibacterial activity was evaluated by a microculture technique described previously [20], except for a 1:100 reduction of the seeding density of T. maritimum NBRC16015. Cytotoxicity assay 3Y1 rat embryonic fibroblastic cells were maintained in low-glucose DMEM medium containing ʟ

One-pot synthesis of isosorbide from cellulose or lignocellulosic biomass: a challenge?

• Isaline Bonnin,
• Raphaël Mereau,
• Thierry Tassaing and
• Karine De Oliveira Vigier

Beilstein J. Org. Chem. 2020, 16, 1713–1721, doi:10.3762/bjoc.16.143

• . Isosorbide is obtained after the hydrolysis of cellulose to glucose, followed by the hydrogenation of glucose to sorbitol that is then dehydrated to isosorbide. The one-pot process requires an acid and a hydrogenation catalyst. Several parameters are of importance during the direct conversion of (ligno

• ; isosorbide; lignocellulosic biomass; Introduction Cellulose, a homopolymer of ᴅ-glucose, is the most abundant component of lignocellulosic biomass. Cellulose is a crystalline polymer due to its intra- and intermolecular hydrogen bond network. The conversion of cellulose to added value chemicals has received

• a lot of interest due to the rarefaction of fossil oil and environmental concerns. One of the interesting reactions is the conversion of cellulose to isosorbide, a 1,4:3,6-dianhydrohexitol [1]. This reaction occurs in several steps: 1) hydrolysis of cellulose to glucose 2) hydrogenation of glucose

Synthesis of Streptococcus pneumoniae serotype 9V oligosaccharide antigens

• Sharavathi G. Parameswarappa,
• Claney L. Pereira and
• Peter H. Seeberger

Beilstein J. Org. Chem. 2020, 16, 1693–1699, doi:10.3762/bjoc.16.140

• pentasaccharide RU with glucuronic acid at the non-reducing end. Results and Discussion The SP 9V linear pentasaccharide RU 1 contains ᴅ-glucuronic acid (ᴅ-GlcpA), ᴅ-galactose (ᴅ-Galp), 2-acetamido-2-deoxy-ᴅ-mannose (ᴅ-ManpNAc), and ᴅ-glucose (ᴅ-Glcp) units. Several cis glycosidic linkages, including a β

• trisaccharide will be prepared from five differentially protected building blocks (8–12) that will ensure the desired stereochemical outcome during the glycosylations. The synthesis of trisaccharide 25 commenced with the union of glucose thioglycoside 12 with C5-linker alcohol 13 to yield the corresponding

• derived from acceptor 19. To circumvent the challenging β-mannosylation, the mannosamine unit was installed via the C-2 inversion of glucose at the trisaccharide stage. For that purpose, the C-2 levulinate ester in compound 22 was removed and the resulting secondary alcohol 23 was converted to the azide

Recent synthesis of thietanes

• Jiaxi Xu

Beilstein J. Org. Chem. 2020, 16, 1357–1410, doi:10.3762/bjoc.16.116

• succeeded in the synthesis of a 4’,4’-spirothietane-2’,N3-cycloadenosine 46 as a highly constrained analogue of 5’-deoxy-5’-methylthioadenosine. They first prepared tritosylate derivative 44 from D-glucose which was treated with KSAc to give the spirothietane derivative 45. The latter compound was further