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Search for "carbohydrates" in Full Text gives 184 result(s) in Beilstein Journal of Organic Chemistry.

Switchable molecular tweezers: design and applications

  • Pablo Msellem,
  • Maksym Dekthiarenko,
  • Nihal Hadj Seyd and
  • Guillaume Vives

Beilstein J. Org. Chem. 2024, 20, 504–539, doi:10.3762/bjoc.20.45

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Published 01 Mar 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

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  • intelligence in combination with spectroscopy-augmented mass spectrometry for carbohydrates sequencing and glycomics applications. Keywords: Bayesian neural network; deep learning; glycomics; IR; spectroscopy; Introduction DNA and protein sequencing technologies that aim at determining the structure of a
  • biopolymer have been established decades ago and are commonly used in a routine and automated manner. However, the development of such technology for the sequencing of the third class of biological polymer – glycans, also known as carbohydrates, saccharides, or "sugars" – lags far behind. This lack of
  • building blocks with distinct molecular structures, carbohydrates feature hundreds of building blocks – many of them coming in groups of closely related isomers with ambiguous molecular structures – and they form complex, branched arrangements due to the versatility of the glycosidic bond (position and
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Published 05 Dec 2023

Synthesis of 5-arylidenerhodanines in L-proline-based deep eutectic solvent

  • Stéphanie Hesse

Beilstein J. Org. Chem. 2023, 19, 1537–1544, doi:10.3762/bjoc.19.110

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  • due to its rich chemistry and readily availability from carbohydrates [25]. We synthesized HMF according to a modified procedure of Cao et al. [26]. Fructose and tetraethylammonium chloride were heated to 120 °C for 2 h and the reaction media was extracted by THF to recover crude HMF after
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Published 04 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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  • such as 2 and 3 and did not. Recently the solid complex of CO2 and 1 have been studied as a food product additive [9][10][11]. Anions of 1 in DMSO have been found to have a high capacity for capturing of CO2 [12]. Being cheap, biodegradable and eco-friendly these carbohydrates might form the basis in
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Published 17 Jul 2023

Linker, loading, and reaction scale influence automated glycan assembly

  • Marlene C. S. Dal Colle,
  • Manuel G. Ricardo,
  • Nives Hribernik,
  • José Danglad-Flores,
  • Peter H. Seeberger and
  • Martina Delbianco

Beilstein J. Org. Chem. 2023, 19, 1015–1020, doi:10.3762/bjoc.19.77

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  • ] as well as technological improvements [8][9] permitted access to highly complex carbohydrates [10]. Still, variations in yields are not always ascribable to the AGA process [11][12][13][14][15][16]. Dissimilar structures are assembled in high purity as indicated by HPLC analysis of the crude products
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Published 06 Jul 2023

Cassane diterpenoids with α-glucosidase inhibitory activity from the fruits of Pterolobium macropterum

  • Sarot Cheenpracha,
  • Ratchanaporn Chokchaisiri,
  • Lucksagoon Ganranoo,
  • Sareeya Bureekaew,
  • Thunwadee Limtharakul and
  • Surat Laphookhieo

Beilstein J. Org. Chem. 2023, 19, 658–665, doi:10.3762/bjoc.19.47

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  • enzyme responsible for the hydrolysis of carbohydrates in the body, is widely used for the management of type 2 diabetes. The agents, such as acarbose, miglitol, and voglibose, can retard the digestion and absorption of dietary carbohydrates [3][4]. Some cassane-type diterpenoids such as pulcherrimin C
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Published 11 May 2023

1,4-Dithianes: attractive C2-building blocks for the synthesis of complex molecular architectures

  • Bram Ryckaert,
  • Ellen Demeyere,
  • Frederick Degroote,
  • Hilde Janssens and
  • Johan M. Winne

Beilstein J. Org. Chem. 2023, 19, 115–132, doi:10.3762/bjoc.19.12

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  • and carbohydrates to various carbocyclic scaffolds. This versatility arises from the possibility to chemoselectively cleave or reduce the sulfur-heterocycle to reveal a versatile C2-synthon. Keywords: 1,4-dithianes; 1,4-dithiins; 2,3-dihydro-1,4-dithiins; heterocycles; target synthesis; Introduction
  • this approach in a number of elegant stereocontrolled syntheses of polyhydroxy compounds and (derivatives of) natural carbohydrates, centering around Palumbo’s versatile building block 66 (Scheme 11c) [62][63][64][65][66][67][68][69][70][71][72][73][74][75][76][77][78][79][80]. The PMB-protected allyl
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Published 02 Feb 2023

Synthesis of 5-unsubstituted dihydropyrimidinone-4-carboxylates from deep eutectic mixtures

  • Sangram Gore,
  • Sundarababu Baskaran and
  • Burkhard König

Beilstein J. Org. Chem. 2022, 18, 331–336, doi:10.3762/bjoc.18.37

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  • ] based on carbohydrates, urea, and inorganic salts as an alternative to conventional solvents for carrying out a variety of organic transformations [32]. The stable melts are environmentally friendly as they are readily available from bulk renewable resources. Their simple production allows the
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Published 22 Mar 2022

Chemical and chemoenzymatic routes to bridged homoarabinofuranosylpyrimidines: Bicyclic AZT analogues

  • Sandeep Kumar,
  • Jyotirmoy Maity,
  • Banty Kumar,
  • Sumit Kumar and
  • Ashok K. Prasad

Beilstein J. Org. Chem. 2022, 18, 95–101, doi:10.3762/bjoc.18.10

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  • postulated a mechanistic pathway for this cyclization process, where two consecutive inversions of configuration at the C5′ centre enabled the retention of stereochemistry. Thus, formation of 5,6-epoxide moieties was common in case of hexose carbohydrates, where the C6-OH group attacked the C5 centre and
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Published 11 Jan 2022

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

  • Ruan Carlos B. Ribeiro,
  • Patricia G. Ferreira,
  • Amanda de A. Borges,
  • Luana da S. M. Forezi,
  • Fernando de Carvalho da Silva and
  • Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

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  • cause several damages to its components, such as carbohydrates, lipids, membrane components, and enzymes that are critical for DNA replication [9][10][11][12]. Most synthetic strategies toward naphthoquinones with potential biological activity start from natural and synthetic naphthoquinones, inserting
  • synthesis of novel 4-amino-1,2-naphthoquinones 43a–c containing carbohydrates and evaluated their antitumor activity in vitro. These compounds were transformed into a series of hydrazones 44a–l with different substituted aryl groups, which were also evaluated against tumor cells. To prepare 43a–c, 18 was
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Published 05 Jan 2022

Advances in mercury(II)-salt-mediated cyclization reactions of unsaturated bonds

  • Sumana Mandal,
  • Raju D. Chaudhari and
  • Goutam Biswas

Beilstein J. Org. Chem. 2021, 17, 2348–2376, doi:10.3762/bjoc.17.153

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  • with Hg(OAc)2 affording the corresponding cyclized pyanosylmethylmercuric chloride derivatives 12 (Scheme 5). This methodology can be used to synthesize rare C-glycosyl carbohydrates from easily available sugars. In a similar manner, stereoselective cyclization of C-glycosyl amino acid derivative 13
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Published 09 Sep 2021

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

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  • β1-4 GlcNAc linkages can then be made using POMGNT1 or POMGNT2 to yield M1 or M3 O-linked mannose structures, respectively. MGAT5B can facilitate β1-4 GlcNAc linkage onto the M1 structure to yield the M2 core. Additional carbohydrates typically found on complex N-linked glycan antennae can then be
  • carbohydrates. Mining TF–glycogene relationships in Cistrome Cancer DB Regulatory potential and gene correlation data were downloaded from the Cistrome Cancer DB in tab-delimited form (http://cistrome.org/CistromeCancer/CancerTarget/) [14]. TF–gene relationships were filtered for the 341 glycogenes in this
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Published 22 Jul 2021

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

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  • . Other examples of the use of column reactors for the catalysis of aldol reactions include: The use of immobilised aldolase enzymes for the synthesis of carbohydrates [114] and the use of a calcinated hydrolactite-packed column for the condensation of furfural with acetone [115], however, this still
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Published 18 May 2021

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

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  • . Keywords: amino sugars; deoxyfluorination; fluorinated carbohydrates; hexosamine hemiacetals; thioglycosides; Introduction Fluorinated carbohydrates are versatile carbohydrate mimetics used to probe or manipulate the recognition of carbohydrates by carbohydrate-binding proteins or carbohydrate-processing
  • desolvation penalty associated with binding of hydrophilic natural carbohydrates [8], and (2) create additional contacts with the binding cavity via electrostatic and dipolar interactions with C–F bonds [9][10], new intermolecular hydrogen bonds [11], or rearrangement of hydrogen bond-mediating water
  • molecules [12]. The fluorination of sugars is also a promising strategy to improve unfavorable pharmacokinetic properties of natural carbohydrates such as low lipophilicity [13][14][15][16] and fast metabolic degradation [17][18][19]. Over the last few years, considerable effort has been expended on the
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Published 11 May 2021

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

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  • predict the enzymes required for the biosynthesis of a given glycan; the subset of the enzyme activities can then be used to generate all of the ganglioside carbohydrates, starting from ceramide, or any other structure. By setting a baseline knockout of enzyme activities, the effects of further knockouts
  • procedure, the parts of the structure identifier that determine the corresponding part of the systematic Svennerholm name (SSN) are shown in bold face. Ganglioside carbohydrates predicted by the model. All structures are linked to ceramide at the base glucose or galactose residue. Ganglioside biosynthetic
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Published 23 Mar 2021

Synthesis and physicochemical evaluation of fluorinated lipopeptide precursors of ligands for microbubble targeting

  • Masayori Hagimori,
  • Estefanía E. Mendoza-Ortega and
  • Marie Pierre Krafft

Beilstein J. Org. Chem. 2021, 17, 511–518, doi:10.3762/bjoc.17.45

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  • , which involves the use of targeting ligands, such as monoclonal antibodies, antibody fragments, proteins, peptides, and other small molecules, including vitamins and carbohydrates [7][8]. The targeting ligands are coupled to the surface of the carrier to selectively target tumor cells that overexpress a
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Published 19 Feb 2021

Supramolecular polymerization of sulfated dendritic peptide amphiphiles into multivalent L-selectin binders

  • David Straßburger,
  • Svenja Herziger,
  • Katharina Huth,
  • Moritz Urschbach,
  • Rainer Haag and
  • Pol Besenius

Beilstein J. Org. Chem. 2021, 17, 97–104, doi:10.3762/bjoc.17.10

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  • , these interactions occur in a multivalent fashion, allowing to overcome drawbacks of the limited strength of noncovalent bonds and to tune the selectivity at the same time [1][2]. The binding of viruses to the membrane of their host cells [3][4][5] as well as the recognition of carbohydrates by lectins
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Published 12 Jan 2021

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

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  • ; polyfluorinated carbohydrates; polyfluoroalditol analogues; Introduction The biological significance of carbohydrates includes, but are not limited to, immune regulation, infection, and cancer metastasis. Research in the field of molecular biology allowed the discovery of glycomimetics to study various
  • biochemical processes [1]. Therefore, the use of bioisosteres of carbohydrates functional groups is a popular approach in glycobiology [2]. As such, the synthesis of fluorosugars, including polyfluorinated analogues, is an interesting strategy to study biological systems [3][4][5][6][7]. The replacement of OH
  • groups by fluorine atoms arise from their similarities in term of polarity and isosteric relationship [3][8]. For a long time, fluorinated carbohydrates have been used as a method to stabilize glycosidic bonds [9][10][11] or for epitope mapping [12][13]. More recently, heavily fluorinated carbohydrates
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Published 25 Nov 2020

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

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  • anomeric mixture of the building block was used for the synthesis of a molecule that could act as an emulsifier only in the presence of Zn2+ ions. Keywords: carbohydrates; emulsifiers; stimuli-responsive; surfactants; synthesis; Introduction Surfactants (surface-active agents) are molecules with both a
  • metal-binding event. This study was carried out by having pyrene fluorophores attached to the two non-chelating positions, giving rise to excimer fluorescence when the distance between them was decreased due to the ring flip [12]. Carbohydrates with gluco stereochemistry have also been used as templates
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Published 17 Nov 2020

Selective recognition of ATP by multivalent nano-assemblies of bisimidazolium amphiphiles through “turn-on” fluorescence response

  • Rakesh Biswas,
  • Surya Ghosh,
  • Shubhra Kanti Bhaumik and
  • Supratim Banerjee

Beilstein J. Org. Chem. 2020, 16, 2728–2738, doi:10.3762/bjoc.16.223

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  • [20][21]. A number of elegant examples of self-assembled multivalent systems targeting biological analytes such as DNA, heparin, proteins, carbohydrates, etc. have been reported in the literature [22][23][24][25][26][27]. ATP is an important bio-anion that is the energy currency in cells and is
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Published 10 Nov 2020

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

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  • the validation of 3D glycoprotein structures. Keywords: electron cryomicroscopy; glycoinformatics; glycomics; Privateer; X-ray crystallography; Introduction Glycosylation-related processes are prevalent in life. The attachment of carbohydrates to macromolecules extends the capabilities of cells to
  • atomic model will be expected as the final result of the study. Modelling of carbohydrates into 3D maps can be more complex than modelling proteins [33], although recent advances in software are closing the gap [34][35][36]. However, to date it remains true that most model building software is protein
  • intermediate interconversion library. A foundation for such interconversion libraries exists in the form of the carbohydrate validation software Privateer. The program is able to compute individual monosaccharide conformations from a glycoprotein model, check whether the modelled carbohydrates atomistic
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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

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  • increases our understanding of biological processes. Representing the structures of carbohydrates has historically been considered to be a complicated task. Starting from the linear form of the Fischer projection, which is certainly not a realistic representation of a carbohydrate structure, there has been
  • 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
  • structures replacing monosaccharides. The description of carbohydrate structures using standard symbolic nomenclature enables easy understanding and communication within the scientific community. Research groups working on carbohydrates have developed schematic depictions with symbols [3] and expansions with
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Published 02 Oct 2020

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

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  • the mechanochemical approach (the B & B, ball milling for boronic acid conjugation) as bioconjugation strategy for the labeling of biocompatible carbohydrates. Fluorescent labeling is of key importance to follow up the fate of molecules and (nano)materials inside cells and in the human body. In this
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Published 11 Sep 2020

How and why plants and human N-glycans are different: Insight from molecular dynamics into the “glycoblocks” architecture of complex carbohydrates

  • Carl A. Fogarty,
  • Aoife M. Harbison,
  • Amy R. Dugdale and
  • Elisa Fadda

Beilstein J. Org. Chem. 2020, 16, 2046–2056, doi:10.3762/bjoc.16.171

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  • relationships in complex carbohydrates, with important implications in glycoengineering design. Keywords: complex carbohydrates; fucose; glycoblocks; molecular dynamics; molecular recognition; N-glycans; xylose; Introduction Complex carbohydrates (or glycans) are an essential class of biomolecules, directly
  • invoked when discussing other biopolymers or complex carbohydrates. In the specific case of glycans, the structural complexity, in terms of the diversity of monosaccharides, the linkages’ stereochemistry and the branched scaffolds, makes the already difficult case even more intricate. Nevertheless, the
  • ultimately understand more clearly the relationships between sequence and structure in complex carbohydrates. Representative structures of the plant N-glycans studied in this work with corresponding nomenclature. The letters f, x, and g indicate the presence of Fuc, Xyl and β(1-3) Gal, respectively, and ng
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Published 21 Aug 2020

Nonenzymatic synthesis of anomerically pure, mannosyl-based molecular probes for scramblase identification studies

  • Giovanni Picca,
  • Markus Probst,
  • Simon M. Langenegger,
  • Oleg Khorev,
  • Peter Bütikofer,
  • Anant K. Menon and
  • Robert Häner

Beilstein J. Org. Chem. 2020, 16, 1732–1739, doi:10.3762/bjoc.16.145

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  • citronellol derivative via a phosphodiester bridge. Moreover, a novel phosphoramidite chemistry-based method offers a straightforward approach for the non-enzymatic incorporation of the saccharide moiety in an anomerically pure form. Keywords: carbohydrates; citronellol; phosphoramidite; photoclickable
  • . Reports of using phosphoramidite chemistry for the preparation of carbohydrates via the anomeric position are relatively rare [18][19][20][21][22][23]. Alternatively, the H-phosphonate approach has been used to convert carbohydrates into phosphate-linked derivatives at the anomeric center [24][25][26][27
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Published 20 Jul 2020
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