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

• Michal M. Wieclaw Bartlomiej Furman Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44/52, 01-224, Warsaw, Poland 10.3762/bjoc.17.12 Abstract Herein we present the direct asymmetric synthesis of tetrazole-functionalized 1-deoxynojirimycin derivatives from simple sugars via a

Selected peptide-based fluorescent probes for biological applications

• Debabrata Maity

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

• of the PDA liposomes to about 48% of the initial value (Figure 10B). The calculated binding constant from Stern–Volmer analysis of fluorescence titration is 1.5 × 106 M−1. This system is very selective towards LPS as other analytes, including nucleotides, anionic sugars, and ctDNA did not increase

Using multiple self-sorting for switching functions in discrete multicomponent systems

• Amit Ghosh and
• Michael Schmittel

Beilstein J. Org. Chem. 2020, 16, 2831–2853, doi:10.3762/bjoc.16.233

• cytosine (C) [2]. Similarly, proteins, like microtubules and actin filaments, are self-sorted on the molecular level in living cells [3]. Furthermore, the smaller molecules of life such as sugars [4], peptides, and fatty acids [5] undergo self-sorting in the construction of a cell [6][7]. The above

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

• interoperability; Linear Code monosaccharides may not be sufficient for every project while IUPAC-extended nomenclature [18] is actively maintained to ensure complete coverage of known sugars. If a user wants to specify that they are using LiCoRR with IUPAC monosaccharides, they can specify it as “LiCoRRICE” the

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

Azo-dimethylaminopyridine-functionalized Ni(II)-porphyrin as a photoswitchable nucleophilic catalyst

• Jannis Ludwig,
• Julian Helberg,
• Hendrik Zipse and
• Rainer Herges

Beilstein J. Org. Chem. 2020, 16, 2119–2126, doi:10.3762/bjoc.16.179

• of sugars [6], enzyme mimics [7], and the utilization of intermolecular cooperative effects [8] are further applications of photoswitchable catalysis. Particularly interesting and close to our approach is an early work by Inoue et al. who achieved control of the transformation of CO2 and 1,2

One-pot synthesis of oxazolidinones and five-membered cyclic carbonates from epoxides and chlorosulfonyl isocyanate: theoretical evidence for an asynchronous concerted pathway

• Esra Demir,
• Ozlem Sari,
• Yasin Çetinkaya,
• Ufuk Atmaca,
• Safiye Sağ Erdem and
• Murat Çelik

Beilstein J. Org. Chem. 2020, 16, 1805–1819, doi:10.3762/bjoc.16.148

• natural products ranging from small molecules, such as sugars, lipids and amino acids to huge molecules [56]. Computational results A detailed mechanistic investigation of the synthesis of oxazolidinone and five-membered cyclic carbonate derivatives by the reaction between epoxide 7f and CSI has been

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

• of isosorbide. Another important factor is the nature of the feedstocks used. Hence, most of the isosorbide syntheses are from pure cellulose and sugars as substrates, such as microcrystalline cellulose and glucose, while studies describing an isosorbide synthesis from lignin-containing cellulosic

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

• mechanisms of the interaction of glycopeptides with the cell surface [16]. Our focus lay on the preparation of glycopeptide libraries containing ʟ-asparagine since many saccharides on the cell surface are N-glycosidically linked to this amino acid [8]. The most abundant sugars found in these asparagine

• -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

Convenient synthesis of the pentasaccharide repeating unit corresponding to the cell wall O-antigen of Escherichia albertii O4

• Tapasi Manna,
• Arin Gucchait and
• Anup Kumar Misra

Beilstein J. Org. Chem. 2020, 16, 106–110, doi:10.3762/bjoc.16.12

• of pentasaccharide 1 was achieved using a convergent as well as a block synthetic strategy. For this purpose, a series of suitably functionalized monosaccharide intermediates 2 [20], 3 [21], 4 [22], 5 [23], 6 [24] and 7 [25] were prepared from the commercially available reducing sugars utilizing the

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

• ; lipopolysaccharide; Introduction Glycosyltransferases are important enzymes that accomplish the transfer of activated sugar phosphates onto their respective acceptor molecules [1]. In most cases, nucleotide diphosphate sugars serve as the reactive species, but lipid-linked diphosphate derivatives are equally

• ). 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

• have reported one-pot multienzyme synthetic protocols for 2,7-anhydro-Neu5Ac [17][18][19]. Our group has developed one-pot syntheses of several anhydro sugars via microwave (MW)-assisted intramolecular anomeric protection (iMAP) of silylated sugars as well as ring-opening protocols for their 1,6

• Ac2O afforded glycal 13 (Table 1, entries 1–4). None of these conditions were successful for the acetolysis of these 2,7-anhydro derivatives, although they worked for the 1,6-anhydro sugars [29][32][33]. Adding 10 equiv of acetic acid to suppress the 2,3-elimination reaction failed to give the desired

• in the synthesis of inhibitors for N-acetylneuraminidases from different sources [42]. The ring opening of 5 was not trivial since the substrate had a sterically hindered quaternary anomeric center, unlike the tertiary anomeric center C-1 of 1,6-anhydro sugars [29][30][31][32][33][43]. Furthermore

Regioselectivity of glycosylation reactions of galactose acceptors: an experimental and theoretical study

• Enrique A. Del Vigo,
• Carlos A. Stortz and
• Carla Marino

Beilstein J. Org. Chem. 2019, 15, 2982–2989, doi:10.3762/bjoc.15.294

• supported by theoretical studies [10][11]. ᴅ-Galactose (ᴅ-Gal) is one of the most abundant sugars in nature and a component of oligosaccharides and glycoconjugates with relevant functions [12]. Following a methodology previously applied to ᴅ-glucosamine acceptors [8] with some modifications, in the present

A green, economical synthesis of β-ketonitriles and trifunctionalized building blocks from esters and lactones

• Daniel P. Pienaar,
• Kamogelo R. Butsi,
• Amanda L. Rousseau and
• Dean Brady

Beilstein J. Org. Chem. 2019, 15, 2930–2935, doi:10.3762/bjoc.15.287

• example, in sugars, hemiacetal pyranoses (due to reduced bond angle strain) are energetically much more favored in solution compared to the corresponding 5-membered furanoses [17]. Significantly, 1H (500 MHz) and 13C NMR (126 MHz) of the purified product 6 (pure by TLC) indicated traces of what appears to

Bacterial terpene biosynthesis: challenges and opportunities for pathway engineering

• Eric J. N. Helfrich,
• Geng-Min Lin,
• Christopher A. Voigt and
• Jon Clardy

Beilstein J. Org. Chem. 2019, 15, 2889–2906, doi:10.3762/bjoc.15.283

• rearrangements, creating the basic hydrocarbon skeleton of a terpene [10][11]. This basic hydrocarbon skeleton is then modified to generate a large number of terpenoid structures, which can be further modified by addition of other building blocks, like sugars, amino acids, or fatty acids [12]. Terpenes are named

Palladium-catalyzed synthesis and nucleotide pyrophosphatase inhibition of benzo[4,5]furo[3,2-b]indoles

• Hoang Huy Do,
• Saif Ullah,
• Alexander Villinger,
• Joanna Lecka,
• Jean Sévigny,
• Peter Ehlers,
• Jamshed Iqbal and
• Peter Langer

Beilstein J. Org. Chem. 2019, 15, 2830–2839, doi:10.3762/bjoc.15.276

• aryl substituent located on the nitrogen atom. Nucleotide pyrophosphatase activity Nucleotide pyrophosphatases belong to the family of ecto-nucleotidases [34][35]. They can hydrolyze nucleotides, dinucleotides, and nucleotide sugars, e.g., ATP, ADP, NAD+, ADP-ribose and diadenosine polyphosphates [36

Chemical synthesis of the pentasaccharide repeating unit of the O-specific polysaccharide from Escherichia coli O132 in the form of its 2-aminoethyl glycoside

• Debasish Pal and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2019, 15, 2563–2568, doi:10.3762/bjoc.15.249

• + 2] strategy where the required monosaccharide building blocks are prepared from commercially available sugars through rational protecting group manipulation. The NIS-mediated activation of thioglycosides was used extensively for the glycosylation reactions throughout. Keywords: 2-aminoethyl

Indium-mediated C-allylation of melibiose

• Christian Denner,
• Manuel Gintner,
• Hanspeter Kählig and
• Walther Schmid

Beilstein J. Org. Chem. 2019, 15, 2458–2464, doi:10.3762/bjoc.15.238

• reported for the first time a tin-mediated allylation of unprotected carbohydrates followed by ozonolysis allowing for easy accessibility of the corresponding elongated sugars [2]. In the same year, Chan and Li introduced indium for the allylation of aldehydes and furthermore demonstrated the applicability

Robust perfluorophenylboronic acid-catalyzed stereoselective synthesis of 2,3-unsaturated O-, C-, N- and S-linked glycosides

• Madhu Babu Tatina,
• Xia Mengxin,
• Rao Peilin and
• Zaher M. A. Judeh

Beilstein J. Org. Chem. 2019, 15, 1275–1280, doi:10.3762/bjoc.15.125

• δ 6.01 (H2, H3) [19][21]. Using the optimized conditions in Table 1, entry 4, we then examined the substrate scope. Therefore, glucal 1a was reacted with various O-nucleophiles (using primary, secondary, tertiary, allyl, propargyl alcohols and sugars), C-nucleophiles (using trimethylsilyl cyanide

• results obtained using boron trifluoride diethyl etherate [32]. We then applied the perfluorophenylboronic acid catalyst to promote the reaction between 2,3,4,6-tetra-O-acetyl-D-glucal (4a) and O- and S-nucleophiles (Figure 2). The Ferrier-catalyzed rearrangements of 2-substituted sugars such as 2,3,4,6

Steroid diversification by multicomponent reactions

• Leslie Reguera,
• Cecilia I. Attorresi,
• Javier A. Ramírez and
• Daniel G. Rivera

Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121

• (e.g., biotin) [64]. Importantly, the effective implementation of on-resin Ugi-4CRs paved the way for the subsequent development of multicomponent macrocyclizations permitting the introduction of PEGs, sugars and fluorescent labels at resin-linked peptides [66][67]. More recently, Wessjohann and Rivera

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

• Dimitri Fayolle,
• Nathalie Berthet,
• Bastien Doumeche,
• Olivier Renaudet,
• Peter Strazewski and
• Michele Fiore

Beilstein J. Org. Chem. 2019, 15, 937–946, doi:10.3762/bjoc.15.90

• addition to its high efficiency and selectivity, the TEC reaction does not require any metal, a key feature for the preparation of potential vaccines. Results and Discussion Preparation of alkyl glycosides from unprotected sugars and lipophilic scaffolds Thioglycolipids are not native in OMV [1], but

Synthesis of a novel category of pseudo-peptides using an Ugi three-component reaction of levulinic acid as bifunctional substrate, amines, and amino acid-based isocyanides

• Maryam Khalesi,
• Azim Ziyaei Halimehjani and
• Jürgen Martens

Beilstein J. Org. Chem. 2019, 15, 852–857, doi:10.3762/bjoc.15.82

• by acid catalysis from renewable resources, such as sugars, lignocellulosic biomass and waste materials [18]. It can be used as a bifunctional precursor for the synthesis of pharmaceuticals, plasticizers, and different additives [19]. Furthermore, it is recognized as an excellent starting material

Synthesis of acylglycerol derivatives by mechanochemistry

• Karen J. Ardila-Fierro,
• Andrij Pich,
• Marc Spehr,
• José G. Hernández and
• Carsten Bolm

Beilstein J. Org. Chem. 2019, 15, 811–817, doi:10.3762/bjoc.15.78

• loads has led to mechanoenzymatic transformations [5][6][7], and to synthesize amino acid derivatives [8][9][10] and peptides [11][12][13] by ball milling and extrusion techniques. Similarly, mechanochemical derivatizations of sugars and sugar derivatives such as cyclodextrins (CDs) have proven

Design and synthesis of multivalent α-1,2-trimannose-linked bioerodible microparticles for applications in immune response studies of Leishmania major infection

• Chelsea L. Rintelmann,
• Tara Grinnage-Pulley,
• Kathleen Ross,
• Daniel E. K. Kabotso,
• Angela Toepp,
• Anne Cowell,
• Christine Petersen,
• Balaji Narasimhan and
• Nicola Pohl

Beilstein J. Org. Chem. 2019, 15, 623–632, doi:10.3762/bjoc.15.58

• vary with Leishmania species (>20 species) and life stage of the pathogen, making it challenging to define how the capping sugars interact and modulate host immune responses [21][22][23][24]. Since these cell-surface glycans are structurally diverse and difficult to isolate in appreciable quantities

Cyclopropene derivatives of aminosugars for metabolic glycoengineering

• Jessica Hassenrück and
• Valentin Wittmann

Beilstein J. Org. Chem. 2019, 15, 584–601, doi:10.3762/bjoc.15.54

• can be ligated through the inverse electron-demand Diels–Alder (DAinv) reaction with 1,2,4,5-tetrazines [13][14][15][16][17]. This reaction is advantageous since it is fast, irreversible, and does not require a toxic heavy metal catalyst. Different terminal alkenes that are connected to sugars by an

• of the deacetylated (water-soluble) sugars, the performance of the sugars in MGE, and the assessment of their metabolic acceptance. The studies uncovered that Ac4ManNCp is much better accepted than Ac4ManNCyoc although their membrane staining intensity after MGE is comparable. The high metabolic

• linkage has a higher impact on the reaction rate than the removal of the methyl group; k2 of ManNCyoc is eleven times higher than that of ManNCp. In conclusion, the three cyclopropene-modified sugars rank in the order ManNCyc, ManNCp, and ManNCyoc with the latter being the fastest. Metabolic