Nomimicins B–D, new tetronate-class polyketides from a marine-derived actinomycete of the genus Actinomadura

• Zhiwei Zhang,
• Tao Zhou,
• Taehui Yang,
• Keisuke Fukaya,
• Enjuro Harunari,
• Shun Saito,
• Katsuhisa Yamada,
• Chiaki Imada,
• Daisuke Urabe and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2194–2202, doi:10.3762/bjoc.17.141

• Actinomadura geliboluensis A8036T (DDBJ accession number HQ157187). Fermentation Actinomadura sp. AKA43 cultured on Bn-2 agar medium (soluble starch 0.5%, glucose 0.5%, meat extract (Kyokuto Pharmaceutical Industrial Co., Ltd.) 0.1%, yeast extract (Difco Laboratories) 0.1%, NZ-case (Wako Chemicals USA, Inc

• .) 0.2%, NaCl 0.2%, CaCO3 0.1%, and agar 1.5% in distilled water of pH 7.0) was inoculated into a 500 mL K-1 flask containing 100 mL of the V-22 seed medium (soluble starch 1%, glucose 0.5%, NZ-case 0.3%, yeast extract 0.2%, tryptone (Difco Laboratories) 0.5%, K2HPO4 0.1%, MgSO4·7H2O 0.05%, and CaCO3 0.3

• % in distilled water of pH 7.0). The flask was shaken on a rotary shaker (200 rpm) at 30 °C for 4 days. For the production of nomimicins B (1) and C (2), the seed culture (3 mL) was transferred into 20 500 mL K-1 flasks, each containing 100 mL of the A16 production medium (glucose 2%, Pharmamedia

Progress and challenges in the synthesis of sequence controlled polysaccharides

• Giulio Fittolani,
• Theodore Tyrikos-Ergas,
• Denisa Vargová,
• Manishkumar A. Chaube and
• Martina Delbianco

Beilstein J. Org. Chem. 2021, 17, 1981–2025, doi:10.3762/bjoc.17.129

• methodologies or post-extraction modifications are not discussed. Review Glucose-based polysaccharides Cellulose Cellulose is a polymer consisting of glucose units connected by β(1–4) glycosidic bonds. It is mainly found in two allomorphs – Cellulose I (natural) and Cellulose II (synthetic) – that differ in the

• (between 5 and 14) could be obtained tuning the concentration of glucose (2a) or cellobiose (2b) primer acceptor [65]. Polymerization conducted under macromolecular crowding conditions using water-soluble polymers produced hydrogels consisting of cellulose and gelatin networks [54][66][67][68][69]. A study

• geometries were observed with a block wise arrangement of methyl groups. As chemical synthesis offers high flexibility in terms of manipulation, non-carbohydrate moieties can be exploited to guide the geometry of the resulting compounds. β(1–4)-Linked glucose chains were connected parallel via an

A systems-based framework to computationally describe putative transcription factors and signaling pathways regulating glycan biosynthesis

• Theodore Groth,
• Rudiyanto Gunawan and
• Sriram Neelamegham

Beilstein J. Org. Chem. 2021, 17, 1712–1724, doi:10.3762/bjoc.17.119

• by the UDP-glucose:ceramide glucosyltransferase (UGCG), which transfers the first glucose. Following this, lactosylceramide is formed by the action of the β1-4GalT activity of B4GalT5 (and possibly also B4GalT3, 4, and 6). The GalCer core is typically structurally small and is made by UDP

• gangliosides. UGCG is included to consider the addition of glucose to ceramide. ST3GAL5 and ST8SIA enzymes are added to take the core ganglioside structures to the a, b, and c levels. B4GALTs and B4GALNT1 are included to account for ganglioside elongation. Decoration of the gangliosides with sialic acid occurs

A recent overview on the synthesis of 1,4,5-trisubstituted 1,2,3-triazoles

• Pezhman Shiri,
• Ali Mohammad Amani and
• Thomas Mayer-Gall

Beilstein J. Org. Chem. 2021, 17, 1600–1628, doi:10.3762/bjoc.17.114

• (n = 1–3). For azides with n = 3, the reaction was performed using alkynes bearing rather complex R2 substituents, such as tyrosine, glucose, clofibrate, vitamin E, estrone, and oleanane triterpenes, which tolerated the reaction conditions and afforded the corresponding triazoles 77 fused with a six

• were screened, producing a moderate to high yield of the desired products. Moreover, alkynes based on complex molecules, such as glucose, tyrosine, clofibrate, estrone, oleanane triterpenes, and vitamin E tolerated the reaction conditions and afforded the corresponding triazolo disulfides (Scheme 28

• . This method was then extended to ketone, tosyl, and phthalimide groups on alkyl azides to produce the desired triazole derivatives. The ethylene glycol-, phenylalanine-, and glucose-derived azides were also good candidates to furnish the triazole derivatives. This protocol provides access to various

Recent advances in the application of isoindigo derivatives in materials chemistry

• Andrei V. Bogdanov and
• Vladimir F. Mironov

Beilstein J. Org. Chem. 2021, 17, 1533–1564, doi:10.3762/bjoc.17.111

• glucose in solution (see polymer 62) [108][109]. The limit of sensitivity of the sensor for nitrogen dioxide was 60 ppm and for glucose 0.026 mM. For the example of the fairly simple arylamine series 63, the possibility of using isoindigo polymer for the detection of explosives (trinitrophenol and

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• :5,6-di-O-isopropylidene-ᴅ-glucose [50]. Furanoside 42 was reacted with the silyl-protected nucleobases 43a–c and 47a,b in the presence of trimethylsilyl trifluoromethanesulfonate in acetonitrile to give the 3′-azido-3′-deoxy-β-ᴅ-ribonucleosides 44a–c and 48a,b via Vorbrüggen coupling reaction. The

Analogs of the carotane antibiotic fulvoferruginin from submerged cultures of a Thai Marasmius sp.

• Birthe Sandargo,
• Leon Kaysan,
• Rémy B. Teponno,
• Christian Richter,
• Benjarong Thongbai,
• Frank Surup and
• Marc Stadler

Beilstein J. Org. Chem. 2021, 17, 1385–1391, doi:10.3762/bjoc.17.97

• assay in 96-well microtiter plates with YM6.3 media (10 g/L malt extract, 4 g/L glucose, 4 g/L yeast extract, pH 6.3) for filamentous fungi and yeasts, and with BD DifcoTM Mueller Hinton Broth for bacteria. The antimicrobial assays were performed as previously described [13]. Cytotoxicity assay The

A comprehensive review of flow chemistry techniques tailored to the flavours and fragrances industries

• Guido Gambacorta,
• James S. Sharley and
• Ian R. Baxendale

Beilstein J. Org. Chem. 2021, 17, 1181–1312, doi:10.3762/bjoc.17.90

Synthesis of multiply fluorinated N-acetyl-D-glucosamine and D-galactosamine analogs via the corresponding deoxyfluorinated glucosazide and galactosazide phenyl thioglycosides

• Vojtěch Hamala,
• Lucie Červenková Šťastná,
• Martin Kurfiřt,
• Petra Cuřínová,
• Martin Dračínský and
• Jindřich Karban

Beilstein J. Org. Chem. 2021, 17, 1086–1095, doi:10.3762/bjoc.17.85

• synthesis of unprotected multiply-deoxyfluorinated monosaccharides, including a complete series of mono-, di-, and trifluorinated ᴅ-glucose [15], difluorinated [20] and tetrafluorinated [13] ᴅ-galactose, and 2,3,4-trifluoro analogs of ᴅ-mannose, ᴅ-galactose, ᴅ-allose, ᴅ-talose, and ᴅ-altrose [13][21

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

Metal-free glycosylation with glycosyl fluorides in liquid SO₂

• Krista Gulbe,
• Jevgeņija Lugiņina,
• Edijs Jansons,
• Artis Kinens and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 964–976, doi:10.3762/bjoc.17.78

• armed and disarmed glucose and mannose-derived glycosyl fluorides in moderate to excellent yields. A series of pivaloyl-protected O- and S-mannosides, as well as one example of a C-mannoside, are synthesized to demonstrate the scope of the glycosyl acceptors. The formation of the fluorosulfite species

• through the neighboring ester type protecting group assistance. At lower temperatures the glycosylation yield was lower, although full conversion of glucosyl fluoride β-9 was still observed. Compared to the analogue mannose derivative α-1a, glucose β-9 turned out to be less stable and more prone to

• conclusion that the Lewis basic carbonyl oxygen of the acetyl group is more coordinated and less nucleophilic in liquid SO2 than the carbonyl oxygen of the pivaloyl group. The profile of side-products in this glucose series was similar to that observed for fluoride β-9 (see Supporting Information File 1

Simulating the enzymes of ganglioside biosynthesis with Glycologue

• Andrew G. McDonald and
• Gavin P. Davey

Beilstein J. Org. Chem. 2021, 17, 739–748, doi:10.3762/bjoc.17.64

• linear chain comprising of up to four monosaccharide units, containing glucose, galactose and N-acetylgalactosamine, to which are attached a variable number of sialic acid (N-acetylneuraminic acid) residues. The sialic acid content of the oligosaccharide, being anionic at pH 7, results in an overall

• since been rescinded [21].) To this base string are added a list of the sialic acids attached to each monosaccharide in the core, counting using the Roman numeral system, starting from the base glucose (cf. Figure 1). From the non-reducing end, write the position on the core where a sialic acid (or

• extended with a galactose, β4-linked to the glucose, to form lactosylceramide, LacCer, catalyzed by β4Gal-T6 (EC 2.4.1.274). This is the first asialo-ganglioside, with core level 3. Two further extensions are possible, to yield core levels 2 and 1, by adding a GalNAc residue β4-linked to the preceding

Valorisation of plastic waste via metal-catalysed depolymerisation

• Francesca Liguori,
• Carmen Moreno-Marrodán and
• Pierluigi Barbaro

Beilstein J. Org. Chem. 2021, 17, 589–621, doi:10.3762/bjoc.17.53

• monobutyltin oxide, using substoichiometric amounts of isosorbide and succinic acid and no solvent at 230 °C reaction temperature. Isosorbide is a safe chemical [246] that is obtainable on the large scale from renewable glucose [247][248]. Because of this and due to the inherent rigid structure, conferring the

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