Make or break: the thermodynamic equilibrium of polyphosphate kinase-catalysed reactions

• Michael Keppler,
• Sandra Moser,
• Henning J. Jessen,
• Christoph Held and
• Jennifer N. Andexer

Beilstein J. Org. Chem. 2022, 18, 1278–1288, doi:10.3762/bjoc.18.134

• optimisation of biocatalytic syntheses of nucleotides as well as nucleotide regeneration systems (Figure 3a and 3b). In a regeneration system (exemplarily shown for the hexokinase-catalysed phosphorylation of glucose (Figure 3a) the formed ADP has to be converted back to ATP to maintain a sufficient pool of

• mechanism exemplarily shown for the associative reaction pathway. a) Kinases as ATP regeneration enzymes, exemplified by the hexokinase-catalysed ATP-dependent phosphorylation of glucose. The ADP formed is converted back to ATP by pyruvate kinase using phosphoenol pyruvate as the phosphate donor [37]. b

Enantioselective total synthesis of putative dihydrorosefuran, a monoterpene with an unique 2,5-dihydrofuran structure

• Irene Torres-García,
• Josefa L. López-Martínez,
• Rocío López-Domene,
• Manuel Muñoz-Dorado,
• Ignacio Rodríguez-García and
• Miriam Álvarez-Corral

Beilstein J. Org. Chem. 2022, 18, 1264–1269, doi:10.3762/bjoc.18.132

• the perfumery industry [1]. In addition, A. pallens has been used in Indian traditional medicine (Ayurveda) for the treatment of measles, cough, cold, depression, diabetes, and high blood pressure [2]. More recently other biological activities have been reported, such as the blood glucose lowering

A Streptomyces P450 enzyme dimerizes isoflavones from plants

• Run-Zhou Liu,
• Shanchong Chen and
• Lihan Zhang

Beilstein J. Org. Chem. 2022, 18, 1107–1115, doi:10.3762/bjoc.18.113

• General Microbiological Culture Collection Center (CGMCC). Seed culture of this strain was done in ISP-2 medium (yeast extract 0.4 g, malt extract 1 g, glucose 0.4 g, distilled water up to 100 mL, pH 7.2) for 2 days. Isoflavone dimer production was performed on MS agar medium (mannitol 20 g, soy flour 20

Isolation and biosynthesis of daturamycins from Streptomyces sp. KIB-H1544

• Yin Chen,
• Jinqiu Ren,
• Ruimin Yang,
• Jie Li,
• Sheng-Xiong Huang and
• Yijun Yan

Beilstein J. Org. Chem. 2022, 18, 1009–1016, doi:10.3762/bjoc.18.101

• NBRC15816. The strain was cultured in 20 L M15 medium: 30.0 g/L glucose, 1.0 g/L peptone, 5.0 g/L beef paste, 2.5 g/L CaCO3, 5.0 g/L NaCl, 1.0 mL/L trace elements solution (1.0 g/L FeSO4·7H2O, 0.45 g/L CuSO4·5H2O, 1.0 g/L ZnSO4·7H2O, 0.1 g/L MnSO4·4H2O, 0.1 g/L K2MoO4). After extraction and concentration

Terpenoids from Glechoma hederacea var. longituba and their biological activities

• Dong Hyun Kim,
• Song Lim Ham,
• Zahra Khan,
• Sun Yeou Kim,
• Sang Un Choi,
• Chung Sub Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2022, 18, 555–566, doi:10.3762/bjoc.18.58

• the same methods as those used for 1. As a result, the monosaccharide of 2 was identified as ᴅ-glucose (Figure S17, Supporting Information File 1). The anomeric proton configuration of the glucopyranosyl unit was determined to be β-configuration based on the J value (7.7 Hz) [11]. Thus, the structure

Amamistatins isolated from Nocardia altamirensis

• Till Steinmetz,
• Wolf Hiller and
• Markus Nett

Beilstein J. Org. Chem. 2022, 18, 360–367, doi:10.3762/bjoc.18.40

• extraction of Nocardia altamirensis For siderophore production, the strain was grown in 5-L Erlenmeyer flasks containing 1 L of iron-free M9 medium: 7.52 g/L Na2HPO4×2H2O, 3.0 g/L KH2PO4, 0.5 g/L NaCl, 0.5 g/L NH4Cl, 4 g/L glucose, 0.247 g/L MgSO4×7H2O, 0.074 g CaCl2×2H2O, 1 mL biotin (1 mg/mL), 1 mL

Glycosylated coumarins, flavonoids, lignans and phenylpropanoids from Wikstroemia nutans and their biological activities

• Meifang Wu,
• Xiangdong Su,
• Yichuang Wu,
• Yuanjing Luo,
• Ying Guo and
• Yongbo Xue

Beilstein J. Org. Chem. 2022, 18, 200–207, doi:10.3762/bjoc.18.23

• . The ROESY spectrum (Supporting Information File 1, Figure S34, recorded in DMSO-d6) showed correlations of H-3'' and H-1'' /H-5''/HO-4'', indicating the ᴅ-configuration of glucose, while the ROESY correlations of H-1'''/H-3'''/H-5''', H-3'''/H-5''', and H-2'''/H-4''' implied the xylose should be in ᴅ

• by a ROESY correlation between H-6'' and H-1'''. Subsequently, an acid hydrolysis of 1 afforded the products including daphnogitin, a ᴅ-glucose, and a ᴅ-xylose. The absolute configurations of glucopyranosyl and xylopyranosyl was further determined by HPLC analysis of the sugar derivatives (Supporting

• and sugar, respectively. The aqueous residue was concentrated to dryness under N2. The aqueous residue, ᴅ-glucose (2 mg), and ᴅ-xylose standard (2 mg) were separately dissolved in 0.5 mL anhydrous pyridine, and ʟ-cysteine methyl ester hydrochloride (2.0 mg) was then added. Each reaction mixture was

Tenacibactins K–M, cytotoxic siderophores from a coral-associated gliding bacterium of the genus Tenacibaculum

• Yasuhiro Igarashi,
• Yiwei Ge,
• Tao Zhou,
• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku and
• Agus Trianto

Beilstein J. Org. Chem. 2022, 18, 110–119, doi:10.3762/bjoc.18.12

• mL of A11M production medium (pH 7.0) consisting of 2.5% soluble starch, 0.2% glucose, 0.5% yeast extract, 0.5% Hipolypeptone (Wako Pure Chemical Industries, Ltd), NZ amine (Wako Pure Chemical Industries, Ltd), CaCO3 0.3%, and 1% Diaion HP-20 (Mitsubishi Chemical Co.) in natural sea water. The

Unsaturated fatty acids and a prenylated tryptophan derivative from a rare actinomycete of the genus Couchioplanes

• Shun Saito,
• Kanji Indo,
• Naoya Oku,
• Hisayuki Komaki,
• Masashi Kawasaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2021, 17, 2939–2949, doi:10.3762/bjoc.17.203

• extract 0.5%, and glucose 0.2% (pH 7.3) solidified by agar 2%, was inoculated into test tubes (inner diameter, 15 mm; length 16.5 cm) each containing 5 mL of YG seed medium consisting of glucose 1% and yeast extract 1% (pH 7.0). The tubes were shaken at 260 strokes/min at 28 °C for 3 days (TC-500R

• days. Isolation of compounds 1–5 Compounds 1–5 were obtained from a culture fermented in A16 production medium with a composition of glucose 2%, Pharmamedia® (Traders Protein, Memphis, TN, USA) 1%, and CaCO3 0.5%. The pH of the medium was adjusted to 7.0 before autoclaving. At the end of fermentation

• , 221.1148; found, 221.1149. Isolation of 6 Compound 6 was obtained from a culture fermented in modified V22 production medium with a composition of soluble starch 1%, glucose 0.5%, NZ Amine, Type A 0.3%, yeast extract 0.2%, Tryptone 0.5% K2HPO4 0.1%, MgSO4·7H2O 0.05%, and CaCO3 0.3%. The pH of the medium

The ethoxycarbonyl group as both activating and protective group in N-acyl-Pictet–Spengler reactions using methoxystyrenes. A short approach to racemic 1-benzyltetrahydroisoquinoline alkaloids

• Marco Keller,
• Karl Sauvageot-Witzku,
• Franz Geisslinger,
• Nicole Urban,
• Michael Schaefer,
• Karin Bartel and
• Franz Bracher

Beilstein J. Org. Chem. 2021, 17, 2716–2725, doi:10.3762/bjoc.17.183

• ) suspensions were loaded with 4 µM fluo-4/AM (Life Technologies, Eugene, OR) for 30 min at 37 °C. After centrifugation, cells were resuspended in HEPES-buffered saline (HBS), containing 132 mM NaCl, 6 mM KCl, 1 mM MgCl2, 1 mM CaCl2, 10 mM HEPES, and 5.5 mM ᴅ-glucose (pH was adjusted to 7.4 with NaOH) and

Phenolic constituents from twigs of Aleurites fordii and their biological activities

• Kyoung Jin Park,
• Won Se Suh,
• Da Hye Yoon,
• Chung Sub Kim,
• Sun Yeou Kim and
• Kang Ro Lee

Beilstein J. Org. Chem. 2021, 17, 2329–2339, doi:10.3762/bjoc.17.151

• ′), 118.2 (C-6), 115.8 (C-2′), 115.3 (C-6′), 114.6 (C-5), and 109.1 (C-2)] and six glucose carbons [δC 103.0 (C-1′′), 76.7 (C-3′′), 76.5 (C-5′′), 73.7 (C-2′′), 70.2 (C-4′′), and 61.3 (C-6′′)]. The spectroscopic data of compound 1 suggested that it is a typical dihydrobenzofuran neolignan glycoside [9][10

• (Figure 2). The locations of the glucose unit and the methoxy group were confirmed from the observed HMBC correlations of H-1′′/C-9′ and 3-OCH3/C-3, respectively (Figure 2). Acid hydrolysis of 1 was conducted to analyze the aglycone and sugar moiety. The structure of the aglycone (1a) was confirmed as

• demethyldihydrodehydrodiconiferyl alcohol based on the comparison of 1H NMR and MS data [13]. The relatively large coupling constant of the anomeric proton (7.8 Hz) confirmed that the glucose is combined as β-form [14]. ᴅ-Glucose was identified by co-TLC with a standard sample [CHCl3/MeOH/H2O 2:1:0.1, Rf = 0.3)] and GC–MS analysis

(Phenylamino)pyrimidine-1,2,3-triazole derivatives as analogs of imatinib: searching for novel compounds against chronic myeloid leukemia

• Luiz Claudio Ferreira Pimentel,
• Lucas Villas Boas Hoelz,
• Henayle Fernandes Canzian,
• Frederico Silva Castelo Branco,
• Andressa Paula de Oliveira,
• Vinicius Rangel Campos,
• Floriano Paes Silva Júnior,
• Rafael Ferreira Dantas,
• Jackson Antônio Lamounier Camargos Resende,
• Anna Claudia Cunha,
• Nubia Boechat and
• Mônica Macedo Bastos

Beilstein J. Org. Chem. 2021, 17, 2260–2269, doi:10.3762/bjoc.17.144

• -2029TM). The K562 strain was grown in RPMI-1640 medium according to the provider's recommendations [47][48]. Cultivation of WSS-1 cells was performed in DMEM high glucose medium (Vitrocell) according to ATCC recommendations. The media were supplemented with 10% fetal bovine serum (FBS) and 50 mg/MI of

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