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Search for "oligosaccharides" in Full Text gives 169 result(s) in Beilstein Journal of Organic Chemistry.

Elucidating the glycan-binding specificity and structure of Cucumis melo agglutinin, a new R-type lectin

  • Jon Lundstrøm,
  • Emilie Gillon,
  • Valérie Chazalet,
  • Nicole Kerekes,
  • Antonio Di Maio,
  • Ten Feizi,
  • Yan Liu,
  • Annabelle Varrot and
  • Daniel Bojar

Beilstein J. Org. Chem. 2024, 20, 306–320, doi:10.3762/bjoc.20.31

Graphical Abstract
  • , these substructures occurred in many different contexts, such as blood group H, LacdiNAc, or the Sda motif, and particularly in sequences resembling O-glycans, milk oligosaccharides, and glycosphingolipids. At first glance, these two binding specificities may seem unconnected, indicating a rather
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Published 19 Feb 2024

Comparison of glycosyl donors: a supramer approach

  • Anna V. Orlova,
  • Nelly N. Malysheva,
  • Maria V. Panova,
  • Nikita M. Podvalnyy,
  • Michael G. Medvedev and
  • Leonid O. Kononov

Beilstein J. Org. Chem. 2024, 20, 181–192, doi:10.3762/bjoc.20.18

Graphical Abstract
  • and conjugates are important for advancing glycobiology [12][13] and glyco-medicine [14][15]. However, the reliable installation of sialic acid residues in oligosaccharides is a rather difficult issue and poor predictability remains characteristic of the sialylation reaction [16][17][18][19][20][21
  • donors that lead to formation of Neu-α(2-3)-Gal [33][34][37] and Neu-α(2-6)-Gal [32][34][36] glycosidic linkages found in oligosaccharides [59] of biological and medical significance. The supramer approach implies that changes in solute concentration can cause the supramers to rearrange and thus affect
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Published 31 Jan 2024

Synthesis of the 3’-O-sulfated TF antigen with a TEG-N3 linker for glycodendrimersomes preparation to study lectin binding

  • Mark Reihill,
  • Hanyue Ma,
  • Dennis Bengtsson and
  • Stefan Oscarson

Beilstein J. Org. Chem. 2024, 20, 173–180, doi:10.3762/bjoc.20.17

Graphical Abstract
  • electrospray ionisation (ESI) in positive mode. MALDI–TOF mass spectrometry data were recorded on a Scientific Analysis Instruments MALDI–TOF mass spectrometer in reflectron mode for oligosaccharides and in linear mode for glycoconjugates. Samples were prepared by pre-mixing 1 µL of a solution containing the
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Published 30 Jan 2024

GlAIcomics: a deep neural network classifier for spectroscopy-augmented mass spectrometric glycans data

  • Thomas Barillot,
  • Baptiste Schindler,
  • Baptiste Moge,
  • Elisa Fadda,
  • Franck Lépine and
  • Isabelle Compagnon

Beilstein J. Org. Chem. 2023, 19, 1825–1831, doi:10.3762/bjoc.19.134

Graphical Abstract
  • proposed to identify the presence of structural features in oligosaccharides based on their gas-phase IR spectra [11]. To the best of our knowledge, machine learning classification studies have not been reported to identify saccharides using MS–IR carbohydrate analysis. Here, we report a study of a
  • oligosaccharides resulting from the fragmentation of a larger precursor possess a very specific IR fingerprint in the 2–4 microns spectral range, that is highly valuable to resolve all types of isomers [4]. Typical experimental IR fingerprint data are shown in Figure 1: they feature the intensities of the
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Published 05 Dec 2023

Cyclodextrins permeabilize DPPC liposome membranes: a focus on cholesterol content, cyclodextrin type, and concentration

  • Ghenwa Nasr,
  • Hélène Greige-Gerges,
  • Sophie Fourmentin,
  • Abdelhamid Elaissari and
  • Nathalie Khreich

Beilstein J. Org. Chem. 2023, 19, 1570–1579, doi:10.3762/bjoc.19.115

Graphical Abstract
  • content membrane increase. Keywords: cholesterol; cyclodextrins; liposome; membrane permeability; Introduction Cyclodextrins (CDs) are a family of cyclic oligosaccharides made of glucopyranose units connected by α-1,4-glycosidic bonds. They possess a cone-shaped molecular structure with a hydrophobic
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Published 17 Oct 2023

CO2 complexation with cyclodextrins

  • Cecilie Høgfeldt Jessen,
  • Jesper Bendix,
  • Theis Brock Nannestad,
  • Heloisa Bordallo,
  • Martin Jæger Pedersen,
  • Christian Marcus Pedersen and
  • Mikael Bols

Beilstein J. Org. Chem. 2023, 19, 1021–1027, doi:10.3762/bjoc.19.78

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  • from industrial processes, power generation, and transportation contribute significantly to global warming and climate change. Carbon capture and storage (CCS) technologies are essential to reduce these emissions and mitigate the effects of climate change. Cyclodextrins (CDs), cyclic oligosaccharides
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Published 17 Jul 2023

Continuous flow synthesis of 6-monoamino-6-monodeoxy-β-cyclodextrin

  • János Máté Orosz,
  • Dóra Ujj,
  • Petr Kasal,
  • Gábor Benkovics and
  • Erika Bálint

Beilstein J. Org. Chem. 2023, 19, 294–302, doi:10.3762/bjoc.19.25

Graphical Abstract
  • ; monosubstitution; reduction; Introduction Cyclodextrins (CDs), as cyclic oligosaccharides, consist of a macrocyclic ring of glucose subunits linked by α-1,4-glycosidic bonds [1]. They are widely used in pharmaceutical, food and chemical industries, as well as in agriculture. It has been known for decades, that CD
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Published 09 Mar 2023

Preparation of β-cyclodextrin/polysaccharide foams using saponin

  • Max Petitjean and
  • José Ramón Isasi

Beilstein J. Org. Chem. 2023, 19, 78–88, doi:10.3762/bjoc.19.7

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  • Max Petitjean Jose Ramon Isasi Department of Chemistry. University of Navarra. 31080 Pamplona, Spain 10.3762/bjoc.19.7 Abstract Cyclodextrins, cyclic oligosaccharides with a hydrophobic cavity that form inclusion complexes with nonpolar molecules, can be used to functionalize other
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Published 24 Jan 2023

Inclusion complexes of the steroid hormones 17β-estradiol and progesterone with β- and γ-cyclodextrin hosts: syntheses, X-ray structures, thermal analyses and API solubility enhancements

  • Alexios I. Vicatos,
  • Zakiena Hoossen and
  • Mino R. Caira

Beilstein J. Org. Chem. 2022, 18, 1749–1762, doi:10.3762/bjoc.18.184

Graphical Abstract
  • pharmaceutical industry for many decades. However, the complexation of APIs with cyclodextrins (cyclic oligosaccharides) resulting in the formation of inclusion complexes, has proven to be a versatile technology for overcoming not only the poor aqueous solubility of APIs, but also unfavourable properties such as
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Published 22 Dec 2022

Cyclodextrin-based Schiff base pro-fragrances: Synthesis and release studies

  • Attila Palágyi,
  • Jindřich Jindřich,
  • Juraj Dian and
  • Sophie Fourmentin

Beilstein J. Org. Chem. 2022, 18, 1346–1354, doi:10.3762/bjoc.18.140

Graphical Abstract
  • molecules and protect those agents from environmental degradation [1][2]. Cyclodextrins (CDs) serve as one of the simplest encapsulating systems. CDs are cyclic oligosaccharides composed of 1→4 linked α-ᴅ-glucopyranose units (6, 7, and 8 for the most common α-, β-, and γ-CD). CDs are well known for their
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Published 28 Sep 2022

Synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of thioglycosides

  • Md Azadur Rahman,
  • Kana Kuroda,
  • Hirofumi Endo,
  • Norihiko Sasaki,
  • Tomoaki Hamada,
  • Hiraku Sakai and
  • Toshiki Nokami

Beilstein J. Org. Chem. 2022, 18, 1133–1139, doi:10.3762/bjoc.18.117

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  • Engineering, Tottori University, 4-101 Koyamacho-minami, Tottori City, 680-8552 Tottori, Japan Koganei Corporation, 3-11-28 Midorimachi, Koganei City, 184-8533 Tokyo, Japan 10.3762/bjoc.18.117 Abstract The synthesis of protected precursors of chitin oligosaccharides by electrochemical polyglycosylation of
  • thioglycosides as monomer is described. Oligosaccharides up to the hexasaccharide were synthesized under optimized reaction conditions. Further, a modified method enabled the synthesis of oligosaccharides up to the octasaccharide by repeating electrolysis with additional monomers. The mechanism of the
  • electrochemical polyglycosylation is also discussed, based on the oxidation potential of the monomer and oligosaccharides. Keywords: electrochemical glycosylation; glucosamine; oligosaccharide; oxidation potential; polyglycosylation; Introduction Chitin oligosaccharides are partial structures of chitin, which
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Published 30 Aug 2022

Total synthesis of the O-antigen repeating unit of Providencia stuartii O49 serotype through linear and one-pot assemblies

  • Tanmoy Halder and
  • Somnath Yadav

Beilstein J. Org. Chem. 2021, 17, 2915–2921, doi:10.3762/bjoc.17.199

Graphical Abstract
  • ][20][21]. For the above purposes, large scale access to pure, defined, and homogeneous samples of the desired LPS oligosaccharides are essential for realization of the goal towards vaccine development against these pathogens [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16][17][18][19][20][21
  • % yield (Scheme 3). The linear synthesis of oligosaccharides is associated with several disadvantages such as multiple steps involving multiple work-up procedures, purifications requiring long time, manpower and the resulting high cost of synthesis and production. Consequently one-pot strategies have
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Published 13 Dec 2021

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

Graphical Abstract
  • polymerization [18], C) chemical synthesis. The use of enzymes has undeniable advantages because it offers the possibility to use unprotected sugars as substrates and guarantees remarkable control of the regio- and stereoselectivity during glycosylation. Mono- or oligosaccharides bearing a reactive leaving group
  • realized using a convergent approach [101]. The process was later simplified using AGA and several XG oligosaccharides were prepared [102]. Representative examples are 19 and 20 (Scheme 3) [103], as well as the galactose-containing compounds 21 and 22 [104]. These compounds permitted to study XG
  • . Several oligosaccharides have been prepared to identify the best PG pattern ensuring a proper balance between BB reactivity, stereoselectivity, and simplicity of deprotection [113][114][115][116][117][118][119][120][121][122][123][124][125]. Ester groups are commonly employed at C-2 position to ensure
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Published 05 Aug 2021

Chemical synthesis of C6-tetrazole ᴅ-mannose building blocks and access to a bioisostere of mannuronic acid 1-phosphate

  • Eleni Dimitriou and
  • Gavin J. Miller

Beilstein J. Org. Chem. 2021, 17, 1527–1532, doi:10.3762/bjoc.17.110

Graphical Abstract
  • this end, synthetic chemistry strategies (both solution and solid phase) have demonstrated exciting capabilities for access to native alginate oligosaccharides in recent years [6][7][8][9][10]. As part of a program to access non-native alginate oligosaccharide sequences, we targeted a synthetic
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Published 05 Jul 2021

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

Graphical Abstract
  • oligosaccharides and glycopeptides under basic aqueous conditions [32][33]. Nevertheless, most of the conventional conditions for glycosyl fluoride activation have considerable drawbacks in terms of atom efficiency and environmental impact. These methods generally require (1) stoichiometric amounts of promoters
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Published 29 Apr 2021

Leveraging glycomics data in glycoprotein 3D structure validation with Privateer

  • Haroldas Bagdonas,
  • Daniel Ungar and
  • Jon Agirre

Beilstein J. Org. Chem. 2020, 16, 2523–2533, doi:10.3762/bjoc.16.204

Graphical Abstract
  • solve. Chiefly among these is the scenario where the experimentally resolved electron density map provides evidence of glycosylation, without enough resolution to derive definite and comprehensive details about the structural composition of the oligosaccharides (Figure 1). Glycan microheterogeneity and
  • heterogeneous [22]. Moreover, oligosaccharides often significantly interfere with the formation of crystal contacts that allow the formation of well-diffracting crystals. Because of this, glycans are often truncated in MX samples to aid crystal formation [27]. In cryo-EM, samples of glycoproteins are vitrified
  • glycoproteins [42]. The mass spectrometric analysis of glycosylated proteins can be with (glycomics) or without (glycoproteomics) the release of oligosaccharides from the glycoprotein. Usually, glycomics and glycoproteomics experiments are carried out together to obtain a complete description of the
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Published 09 Oct 2020

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

Graphical Abstract
  • 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
  • of molecules; thus, it provides challenges in the development of force fields for accurate modelling of such variations in charge distributions. The monosaccharides can further form a large number of oligosaccharides which can enormously increase the conformational space, due to a high number of
  • oligosaccharides containing additional groups like sulfates, phosphates etc. [24] Generally used force fields for the Molecular Mechanics (MD) simulation of carbohydrates are CHARMM [25], GLYCAM [26], and GROMOS [27]. The structural complexity increases the computational cost, which makes simulations of large
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Published 02 Oct 2020

Synthesis of the tetrasaccharide repeating unit of the O-specific polysaccharide of Azospirillum doebereinerae type strain GSF71T using linear and one-pot iterative glycosylations

  • Arin Gucchait,
  • Pradip Shit and
  • Anup Kumar Misra

Beilstein J. Org. Chem. 2020, 16, 1700–1705, doi:10.3762/bjoc.16.141

Graphical Abstract
  • strategies could provide access to large quantities of the oligosaccharides with defined chemical structures and free from biological impurities. Among the nineteen species of Azospirillum, Azospirillum doebereinerae was isolated from the rhizosphere of the biomass producing plant, Miscanthus giganteus [20
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Published 15 Jul 2020

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

Graphical Abstract
  • flexneri pentadecasaccharide that passed phase-I clinical trials [17][18] incorporate defined oligosaccharides. SP 9 contains four capsular types (9A, 9L, 9N and 9V) whereby the most prevalent, 9V (57%) affects young children and 9N (34%) infects adults [19]. CPS of 9V and 9A serotypes differ only in the
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Published 15 Jul 2020

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

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  • Laura Srsan Thomas Ziegler Institute of Organic Chemistry, University of Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany 10.3762/bjoc.16.80 Abstract For investigations on the biological functions of oligosaccharides and peptidomimetics, new asparagine-based mono- and disaccharides
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Published 30 Apr 2020

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

Graphical Abstract
  • -containing oligosaccharides with the desired regioselectivity is to regioselectively protect the Neu5Ac acceptor. Although Neu5Ac with a free primary OH-9 function is easy to obtain, there are only limited ways to distinguish the secondary OH-4 and OH-7 group (Figure 1). In our previous report, we easily
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Published 23 Dec 2019

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

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  • Universitaria, 1428 Buenos Aires, Argentina 10.3762/bjoc.15.294 Abstract Regioselective glycosylations allow planning simpler strategies for the synthesis of oligosaccharides, and thus reducing the need of using protecting groups. With the idea of gaining further understanding of such regioselectivity, we
  • carbohydrates in living systems, oligosaccharides and other glycoconjugates are needed to carry out the corresponding glycobiological studies. The heterogeneity of carbohydrates from natural sources makes their isolation difficult, which results in synthesis being the best alternative to obtain the required
  • amounts of carbohydrate-containing molecules. Due to the chemical nature of carbohydrates, with multiple possible linkage positions giving rise to different regioisomers, with two possible anomeric configurations, the chemical synthesis of complex oligosaccharides is difficult and a rather time-consuming
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Published 19 Dec 2019

Automated glycan assembly of arabinomannan oligosaccharides from Mycobacterium tuberculosis

  • Alonso Pardo-Vargas,
  • Priya Bharate,
  • Martina Delbianco and
  • Peter H. Seeberger

Beilstein J. Org. Chem. 2019, 15, 2936–2940, doi:10.3762/bjoc.15.288

Graphical Abstract
  • , Germany 10.3762/bjoc.15.288 Abstract Arabinomannan (AM) polysaccharides are clinical biomarkers for Mycobacterium tuberculosis (MTB) infections due to their roles in the interaction with host cells and interference with macrophage activation. Collections of defined AM oligosaccharides can help to improve
  • after each glycosylation and further optimized reaction conditions allowed for the synthesis of a series of oligosaccharides, ranging from hexa- to branched dodecasaccharides. Keywords: arabinomannan; automated glycan assembly; capping; Introduction Bacterial infections caused by MTB killed 1.7
  • ]. Identification of novel anti-TB agents that specifically target AMs with high sensitivity are required. Pure AM oligosaccharides may help to identify new lead compounds for the development of diagnostics. Since the isolation of pure oligosaccharides from MTB strains in sufficient quantities is challenging, the
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Published 06 Dec 2019

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

Graphical Abstract
  • chemically synthesized oligosaccharides before [8][9][10]. The corresponding aminopropyl linker has also been used by others [11]. The chemically synthesized oligosaccharide structure will help to elucidate further biological implications of the O-antigen concerned and possible vaccine potential. Results and
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Published 28 Oct 2019

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

Graphical Abstract
  • molecular recognition, cell–cell interaction, immunological recognition and transmission of biological information [4][5][6]. They are easily transformed into important bioactive compounds such as oligosaccharides, glycopeptides, nucleosides, antibiotics, uronic acids and other natural products [1][2][3
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Published 11 Jun 2019
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