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

A smart deoxyribozyme-based fluorescent sensor for in vitro detection of androgen receptor mRNA

• Ekaterina A. Bryushkova,
• Erik R. Gandalipov and
• Julia V. Nuzhina

Beilstein J. Org. Chem. 2020, 16, 1135–1141, doi:10.3762/bjoc.16.100

• electrode, covered by immobilizing enzyme glucose oxidase, for the detection of glucose [1]. A biosensor means a small molecular device that traditionally consists of a bioreceptor (enzyme, cell, aptamer, oligonucleotide, antibody, and other) for the specific recognition of the target molecule and a

A cyclopeptide and three oligomycin-class polyketides produced by an underexplored actinomycete of the genus Pseudosporangium

• Shun Saito,
• Kota Atsumi,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Naoya Oku,
• Md. Rokon Ul Karim,
• Hisayuki Komaki and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 1100–1110, doi:10.3762/bjoc.16.97

• strain 3-44-a(19)T (AB302183). Fermentation Strain RD062863 growing on double-diluted ISP2 agar medium consisting of yeast extract 0.2%, malt extract 0.5%, glucose 0.2%, and agar 2% (pH 7.3) 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 placed in a shaker TC-500R (Takasaki Scientific Instruments Corp.) (260 strokes/min) at 28 °C for 4 days. Then, the seed culture (1 mL) was transferred into 500 mL Erlenmeyer flasks each containing 100 mL of modified A3M production medium

• consisting of glucose 0.5%, glycerol 2%, soluble starch 2%, Pharmamedia (Traders Protein) 1.5%, dry yeast (Kamaishi Hamayuri Yeast, Nihon Tensai Seito Co., Ltd.) 0.3%. The pH of the medium was adjusted to 7.0 before sterilization. The inoculated flasks were placed on a rotary shaker TB98 (Takasaki Scientific

Synthesis of new asparagine-based glycopeptides for future scanning tunneling microscopy investigations

• Laura Sršan and
• Thomas Ziegler

Beilstein J. Org. Chem. 2020, 16, 888–894, doi:10.3762/bjoc.16.80

• -linked structures are N-acetylglycosylamines, glucose, galactose, mannose, cellobiose, lactose, and maltose [19]. Therefore, we intended to prepare glycopeptide structures containing these sugars in a stepwise way, up to tripeptides. An orthogonal Fmoc/t-Bu protecting group strategy was chosen along with

• synthesis of a series of new glycopeptides containing asparagine, tryptophane, alanine, and phenylalanine linked to various saccharides, such as glucose, galactose, mannose, cellobiose, lactose, and maltose. We further compared two common peptide coupling procedures that use HBTU and HATU, respectively. We

Synthesis of disparlure and monachalure enantiomers from 2,3-butanediacetals

• Adam Drop,
• Hubert Wojtasek and
• Bożena Frąckowiak-Wojtasek

Beilstein J. Org. Chem. 2020, 16, 616–620, doi:10.3762/bjoc.16.57

• ensure the required configuration of the asymmetric centers determining the biological activity of this compound. They include the use of naturally occurring chiral substrates, such as ʟ-glutamic acid [13], ʟ-tartaric acid [14][15][16], ᴅ-glucose [17], and sorbitol [18] as starting materials, as well as

Two antibacterial and PPARα/γ-agonistic unsaturated keto fatty acids from a coral-associated actinomycete of the genus Micrococcus

• Amit Raj Sharma,
• Enjuro Harunari,
• Naoya Oku,
• Nobuyasu Matsuura,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2020, 16, 297–304, doi:10.3762/bjoc.16.29

• incubated at 30 °C on a rotary shaker at 200 rpm for two days. Three mL each of the seed culture were inoculated into 29 500 mL K-1 flasks containing 100 mL of A16 production medium, which consisted of glucose 2%, Pharmamedia (Traders Protein, Memphis, TN, USA) 1%, CaCO3 0.5%, Diaion HP-20 (Mitsubishi

Synthesis of C-glycosyl phosphonate derivatives of 4-amino-4-deoxy-α-ʟ-arabinose

• Lukáš Kerner and
• Paul Kosma

Beilstein J. Org. Chem. 2020, 16, 9–14, doi:10.3762/bjoc.16.2

• ). Conversion of benzylated reducing sugars, such as glucose [15], N-acetyl-ᴅ-glucosamine [16], and galactose [17], into the corresponding C-glycosyl phosponates using a Wittig reaction with methylenetriphenylphosphorane furnished the respective glycoenitols, which were then subjected to mercuriocyclization

SnCl₄-catalyzed solvent-free acetolysis of 2,7-anhydrosialic acid derivatives

• Kesatebrhan Haile Asressu and
• Cheng-Chung Wang

Beilstein J. Org. Chem. 2019, 15, 2990–2999, doi:10.3762/bjoc.15.295

• , SnCl4 and Sn(OTf)2 might have formed a coordination bond with the carbonyl oxygen atom of the C-5 NHAc group and the O-6 position of the glucose glucopyranosyl ring. In turn, this retarded the ring-opening reaction. The anchimeric participation of the NHAc group in stabilizing the axial conformation of

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

• Soleiman E. Helaly,
• Wilawan Kuephadungphan,
• Patima Phainuphong,
• Mahmoud A. A. Ibrahim,
• Kanoksri Tasanathai,
• Suchada Mongkolsamrit,
• Janet Jennifer Luangsa-ard,
• Souwalak Phongpaichit,
• Vatcharin Rukachaisirikul and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2968–2981, doi:10.3762/bjoc.15.293

• elucidation Gibellula sp. was cultivated in liquid yeast, malt, and glucose (YMG) medium and extracted as described in the Experimental section. The extracts were purified by HPLC to give pigmentosin A (1) and pigmentosin B (2). Using a similar procedure, compounds 3–6 were obtained from the liquid culture of

• medium, and incubated at 23 °C on a shaker at 140 rpm. The free glucose content of each fermented broth was tentatively monitored using Bayer Diastix Harnzuckerstreifen. After the glucose was depleted, the incubation was prolonged for half of the time each strain had taken for glucose consumption, and

Two new aromatic polyketides from a sponge-derived Fusarium

• Mada Triandala Sibero,
• Tao Zhou,
• Keisuke Fukaya,
• Daisuke Urabe,
• Ocky K. Karna Radjasa,
• Agus Sabdono,
• Agus Trianto and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2019, 15, 2941–2947, doi:10.3762/bjoc.15.289

• KJMT.FP.4.3 cultured on PDA agar was inoculated into 500 mL K-1 flasks each containing V22 seed medium consisting of soluble starch 1%, glucose 0.5%, NZ-case (Sigma-Aldrich, Co., LLC.) 0.3%, yeast extract (Kyokuto Pharmaceutical Industrial, Co., Ltd.) 0.2%, Tryptone (Difco Laboratories) 0.5%, K2HPO4 0.1

• %, MgSO4·7H2O 0.05%, and CaCO3 0.3% (pH 7.0). The flasks were shaken at 30 °C for 4 days on a rotary shaker (200 rpm). The seed culture (3 mL) was transferred into 500 mL K-1 flasks each containing 100 mL of A3M production medium (pH 7.0) consisting of 2.0% soluble starch, 0.5% glucose, 2.0% glycerol, 0.3

Preparation of anthracene-based tetraperimidine hexafluorophosphate and selective recognition of chromium(III) ions

• Qing-Xiang Liu,
• Feng Yang,
• Zhi-Xiang Zhao,
• Shao-Cong Yu and
• Yue Ding

Beilstein J. Org. Chem. 2019, 15, 2847–2855, doi:10.3762/bjoc.15.278

• of Cr3+ ions occupies an important position. Chromium(III) is an essential microelement for humans and animals, and it plays an important role in glucose and lipid metabolism in the body [9][10]. The deficiency of chromium(III) in the human body leads to various diseases, such as diabetes as well as

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• labeling, labeling solutions were checked by UPLC. The external solution was (in mM): 140 NaCl, 2.8 KCl, 2 CaCl2, 2 MgCl2, 10 HEPES, 12 glucose (pH 7.3 with NaOH). Compound 1 (0.05 mM) was dissolved in external solution and sonicated for 5 min. HEK293 cells with green fluorescence were chosen for recording

• KCl, 1.25 NaH2PO4, 7 MgCl2, 0.5 CaCl2, 26 NaHCO3, 10 glucose, 100 sucrose, 3 sodium pyruvate, 1.3 sodium ascorbate equilibrated with 95% O2/5% CO2 (pH 7.3–7.4). The brain slices were then incubated for 15 min at 33 °C in artificial cerebrospinal fluid (ACSF, mM: 125 NaCl, 2.5 KCl, 1.25 NaH2PO4, 1

• MgCl2, 2 CaCl2, 26 NaHCO3, 10 glucose, 3 sodium pyruvate, 1.3 sodium ascorbate; 95% O2/5% CO2, pH 7.3–7.4) and held at room temperature. Brain slices were then transferred to the recording chamber of a BX-61 microscope (Olympus, PennValley, PA, USA) and superfused with ACSF at room temperature. Medial

Skeletocutins M–Q: biologically active compounds from the fruiting bodies of the basidiomycete Skeletocutis sp. collected in Africa

• Tian Cheng,
• Clara Chepkirui,
• Cony Decock,
• Josphat C. Matasyoh and
• Marc Stadler

Beilstein J. Org. Chem. 2019, 15, 2782–2789, doi:10.3762/bjoc.15.270

• standard turbidity in casein-peptone soymeal-peptone (CASO) medium containing 4% glucose at pH 7.0 for biofilm formation. Methanol was used as negative control, while tetracycline was used as positive control. All experiments were made in triplicates. Nematicidal activity assay The nematicidal activity of