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Stereoselective Synthesis of a Fragment of Mycobacterial Arabinan

https://doi.org/10.1021/ol062198j
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What this work says

Outgoing claims: the papers this work cites, builds on, or argues with.

inferredcites →https://doi.org/10.1002/9781444311433openalex-snapshot
Mycobacteria
inferredcites →https://doi.org/10.1016/0008-6215(89)84018-2openalex-snapshot
N.m.r. spectral study of α- and β-l-arabinofuranosides
inferredcites →https://doi.org/10.1016/j.bmc.2005.12.037openalex-snapshot
Synthesis and TNF-α inducing activities of mycoloyl-arabinan motif of mycobacterial cell wall components
inferredcites →https://doi.org/10.1016/j.ijid.2009.11.026openalex-snapshot
Tuberculosis and the tubercle bacillus
inferredcites →https://doi.org/10.1016/j.tetlet.2004.03.100openalex-snapshot
Accelerated glycosylation under frozen conditions
inferredcites →https://doi.org/10.1016/s0140-6736(98)07422-4openalex-snapshot
BCG immunotherapy of bladder cancer: 20 years on
inferredcites →https://doi.org/10.1016/s1367-5931(01)00265-4openalex-snapshot
Chemistry and biology of arabinofuranosyl- and galactofuranosyl-containing polysaccharides
inferredcites →https://doi.org/10.1021/bi00013a015openalex-snapshot
A new interpretation of the structure of the mycolyl-arabinogalactan complex of Mycobacterium tuberculosis as revealed through characterization of oligoglycosylalditol fragments by fast-atom bombardment mass spectrometry and 1H nuclear magnetic resonance spectroscopy
inferredcites →https://doi.org/10.1021/ja00004a067openalex-snapshot
Reactions of phenylfluorocarbene with lithium salts. Absolute kinetics of carbenoid formation
inferredcites →https://doi.org/10.1021/ja01607a028openalex-snapshot
The Dissociation of Sterically Hindered Acids
inferredcites →https://doi.org/10.1021/ja0349610openalex-snapshot
2,3-Anhydrosugars in Glycoside Bond Synthesis. NMR and Computational Investigations into the Mechanism of Glycosylations with 2,3-Anhydrofuranosyl Glycosyl Sulfoxides
inferredcites →https://doi.org/10.1021/jm00257a600openalex-snapshot
Nucleoside Peptides. 6. Synthesis of Certain N-[5-Amino-1-(β-D-ribofuranosyl)imidazole-4-carbonyl]amino Acids Related to Naturally Occurring Intermediates in the Purine Biosynthetic Pathway
inferredcites →https://doi.org/10.1093/glycob/5.6.547openalex-snapshot
Galactofuranose-containing glycoconjugates in trypanosomatids
inferredcites →https://doi.org/10.1128/iai.68.12.6883-6890.2000openalex-snapshot
Maturation of Human Dendritic Cells by Cell Wall Skeleton ofMycobacterium bovisBacillus Calmette-Guerin: Involvement of Toll-Like Receptors
inferredcites →https://doi.org/10.1146/annurev.bi.64.070195.000333openalex-snapshot
THE ENVELOPE OF MYCOBACTERIA

What points at this work

Incoming claims: where this work appears in other papers’ reference lists and arguments.

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Total Synthesis of the Hexasaccharide Arabinan Domain of Mycobacterial Arabinogalactan
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Di-tert-butyldichlorosilane
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Synthetic Approaches to Bioactive Carbohydrates
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SYNTHESIS OF BACTERIAL CELL ENVELOPE COMPONENTS
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General Aspects of the Glycosidic Bond Formation
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Recent Developments in the Construction of cis ‐Glycosidic Linkages
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Stereoselective Glycosylations – Additions to Oxocarbenium Ions
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Selective Glycosylations with Furanosides
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Neue Prinzipien für die Bildung von glycosidischen Bindungen
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A 3,4‐trans‐Fused Cyclic Protecting Group Facilitates α‐Selective Catalytic Synthesis of 2‐Deoxyglycosides
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Synthesis of the Highly Glycosylated Hydrophilic Motif of Extensins
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Regioselective and Stereospecific β‐Arabinofuranosylation by Boron‐Mediated Aglycon Delivery
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New Principles for Glycoside‐Bond Formation
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A 3,4‐trans‐Fused Cyclic Protecting Group Facilitates α‐Selective Catalytic Synthesis of 2‐Deoxyglycosides
inferred← citeshttps://doi.org/10.1002/anie.201404904openalex-snapshot
Synthesis of the Highly Glycosylated Hydrophilic Motif of Extensins
inferred← citeshttps://doi.org/10.1002/anie.202307015openalex-snapshot
Regioselective and Stereospecific β‐Arabinofuranosylation by Boron‐Mediated Aglycon Delivery
inferred← citeshttps://doi.org/10.1002/chem.201100732openalex-snapshot
Neighboring‐Group Participation by C‐2 Ether Functions in Glycosylations Directed by Nitrile Solvents
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Automated Glycan Assembly of Mycobacterial Hexaarabinofuranoside and Docosasaccharide Arabinan (Araf23) Motifs found on Mycobacterium tuberculosis
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GH172 Difructose Dianhydride I Synthase: A Two‐Stepped Journey via Glycosylation and Cyclization Using QM/MM Metadynamics
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NAP Ether Mediated Intramolecular Aglycon Delivery: A Unified Strategy for 1,2‐cis‐Glycosylation
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Silylene/Oxazolidinone Double‐Locked Sialic Acid Building Blocks for Efficient Sialylation Reactions in Dichloromethane
inferred← citeshttps://doi.org/10.1002/ejoc.201700712openalex-snapshot
Expedient Synthesis of a Linear Nonadecaarabinofuranoside of the Mycobacterium tuberculosis Cellular Envelope
inferred← citeshttps://doi.org/10.1002/ejoc.202201110openalex-snapshot
Five Triisopropylsilyl Substituents in Ara‐β‐(1→2)‐Ara Disaccharide Glycosyl Donor Make Unselective Glycosylation Reaction Stereoselective
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Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update covering the period 1999–2000
inferred← citeshttps://doi.org/10.1002/mas.20265openalex-snapshot
Analysis of carbohydrates and glycoconjugates by matrix‐assisted laser desorption/ionization mass spectrometry: An update for the period 2005–2006
inferred← citeshttps://doi.org/10.1007/s11172-010-0397-4openalex-snapshot
Synthesis of covalent conjugates of hexaarabinofuranoside with proteins and their testing as antigens for serodiagnosis of tuberculosis
inferred← citeshttps://doi.org/10.1007/s11172-015-0992-5openalex-snapshot
Synthesis of hexasaccharide fragment of lipoarabonomannan from Mycobacteria: advantages of the benzyl-free approach
inferred← citeshttps://doi.org/10.1007/s11172-022-3371-zopenalex-snapshot
The use of silyl groups in the synthesis of arabinofuranosides
inferred← citeshttps://doi.org/10.1016/b978-0-08-097742-3.00602-9openalex-snapshot
6.01 Synthesis of Glycosides
inferred← citeshttps://doi.org/10.1016/b978-0-12-819475-1.00016-xopenalex-snapshot
1,2-cis O-Glycosylation Methods
inferred← citeshttps://doi.org/10.1016/b978-0-12-819475-1.00064-xopenalex-snapshot
Glycosylation With Furanosides
inferred← citeshttps://doi.org/10.1016/b978-0-240-52118-3.00004-1openalex-snapshot
Formation of the Glycosidic Linkage
inferred← citeshttps://doi.org/10.1016/j.bmc.2010.04.013openalex-snapshot
Effects of frozen conditions on stereoselectivity and velocity of O-glycosylation reactions
inferred← citeshttps://doi.org/10.1016/j.bmc.2022.116849openalex-snapshot
Synthesis of naturally occurring β-l-arabinofuranosyl-l-arabinofuranoside structures towards the substrate specificity evaluation of β-l-arabinofuranosidase
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Indirect approach to C-3 branched 1,2-cis-glycofuranosides: synthesis of aceric acid glycoside analogues
inferred← citeshttps://doi.org/10.1016/j.carres.2008.09.006openalex-snapshot
Synthesis of β-d-arabinofuranosides: stereochemical differentiation between d- and l-enantiomers
inferred← citeshttps://doi.org/10.1016/j.carres.2010.11.002openalex-snapshot
Ring opening of acylated β-d-arabinofuranose 1,2,5-orthobenzoates with nucleophiles allows access to novel selectively-protected arabinofuranose building blocks
inferred← citeshttps://doi.org/10.1016/j.carres.2011.10.004openalex-snapshot
Glycosylation studies on conformationally restricted 3,5-O-(di-tert-butylsilylene)-d-galactofuranosyl trichloroacetimidate donors for 1,2-cis α-d-galactofuranosylation
inferred← citeshttps://doi.org/10.1016/j.carres.2012.05.021openalex-snapshot
Synthesis of branched arabinofuranose pentasaccharide fragment of mycobacterial arabinans as 2-azidoethyl glycoside
inferred← citeshttps://doi.org/10.1016/j.carres.2012.05.025openalex-snapshot
Influence of protecting groups on the anomeric equilibrium; case of the 4,6-O-benzylidene acetal in the mannopyranose series
inferred← citeshttps://doi.org/10.1016/j.carres.2013.10.005openalex-snapshot
Preparation of p-nitrophenyl β-l-arabinofuranoside as a substrate of β-l-arabinofuranosidase
inferred← citeshttps://doi.org/10.1016/j.carres.2014.05.017openalex-snapshot
The use of O-trifluoroacetyl protection and profound influence of the nature of glycosyl acceptor in benzyl-free arabinofuranosylation
inferred← citeshttps://doi.org/10.1016/j.carres.2014.07.024openalex-snapshot
Conformationally restricted 3,5-O-(di-tert-butylsilylene)-d-galactofuranosyl thioglycoside donor for 1,2-cis α-d-galactofuranosylation
inferred← citeshttps://doi.org/10.1016/j.carres.2016.05.009openalex-snapshot
Rapid synthesis of linear homologous oligoarabinofuranosides related to mycobacterial lipoarabinomannan and a neoglycoconjugate thereof
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Bimodal concentration-dependent reactivity pattern of a glycosyl donor: Is the solution structure involved?
inferred← citeshttps://doi.org/10.1016/j.carres.2024.109141openalex-snapshot
Unusual triflic acid-promoted oligomerization of arabinofuranosides during glycosylation
inferred← citeshttps://doi.org/10.1016/j.carres.2024.109204openalex-snapshot
Total synthesis of the hexasaccharide arabinan domain of mycobacterial arabinogalactan
inferred← citeshttps://doi.org/10.1016/j.carres.2024.109252openalex-snapshot
Stereocontrolled 1,2-trans-arabinofuranosylation in the absence of 2-O-acyl group in glycosyl donor
inferred← citeshttps://doi.org/10.1016/j.carres.2025.109622openalex-snapshot
Application of Ara-β-(1 → 2)-Ara diarabinofuranosides with O-TBDPS protective groups in the synthesis of the tetra- and dodecaarabinofuranosides – fragments of mycobacterial polysaccharides
inferred← citeshttps://doi.org/10.1016/j.chembiol.2017.08.014openalex-snapshot
Arabinosylation Modulates the Growth-Regulating Activity of the Peptide Hormone CLE40a from Soybean
inferred← citeshttps://doi.org/10.1016/j.chemphyslip.2019.01.002openalex-snapshot
The synthesis of mycobacterial dimycoloyl diarabinoglycerol based on defined synthetic mycolic acids
inferred← citeshttps://doi.org/10.1016/j.jbc.2021.101324openalex-snapshot
Identification of difructose dianhydride I synthase/hydrolase from an oral bacterium establishes a novel glycoside hydrolase family
inferred← citeshttps://doi.org/10.1016/j.tet.2016.04.038openalex-snapshot
Synthesis of tri- and tetrasaccharide glycosides of (4S)-4-hydroxy-d-proline relevant to the cell wall O-glycans of green alga Chlamydomonas reinhardtii
inferred← citeshttps://doi.org/10.1016/j.tetlet.2011.02.019openalex-snapshot
Formation of orthoester-linked d-arabinofuranose oligosaccharides and their isomerization into the corresponding glycosides
inferred← citeshttps://doi.org/10.1016/j.tetlet.2012.03.016openalex-snapshot
Concise synthesis of an arabinofuranose hexasaccharide present in the cell wall of Mycobacterium tuberculosis
inferred← citeshttps://doi.org/10.1021/acs.accounts.6b00164openalex-snapshot
Twenty Years of Mycobacterial Glycans: Furanosides and Beyond
inferred← citeshttps://doi.org/10.1021/acs.chemrev.8b00036openalex-snapshot
“One-Pot” Protection, Glycosylation, and Protection–Glycosylation Strategies of Carbohydrates
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Automated Chemical Oligosaccharide Synthesis: Novel Approach to Traditional Challenges
inferred← citeshttps://doi.org/10.1021/acs.joc.0c01008openalex-snapshot
A Siloxane-Bridged Glycosyl Donor Enables Highly Stereoselective β-Xylulofuranosylation
inferred← citeshttps://doi.org/10.1021/acs.joc.0c02045openalex-snapshot
Conformationally Constrained Glycosyl Donors as Tools to Control Glycosylation Outcomes
inferred← citeshttps://doi.org/10.1021/acs.joc.1c02374openalex-snapshot
Side Chain Conformation and Its Influence on Glycosylation Selectivity in Hexo- and Higher Carbon Furanosides
inferred← citeshttps://doi.org/10.1021/acs.joc.5b00964openalex-snapshot
Influence of Steric Crowding on Diastereoselective Arabinofuranosylations
inferred← citeshttps://doi.org/10.1021/acs.joc.5b01686openalex-snapshot
Synthetic and Immunological Studies of Mycobacterial Lipoarabinomannan Oligosaccharides and Their Protein Conjugates
inferred← citeshttps://doi.org/10.1021/acs.joc.6b01723openalex-snapshot
Phthalic Anhydride-Mediated Direct Glycosylation of Anomeric Hydroxy Arabinofuranose: Synthesis of Repeating Oligoarabinofuranoside and Tetradecasaccharide Arabinan Motif of Mycobacterial Cell Wall
inferred← citeshttps://doi.org/10.1021/acs.joc.7b01817openalex-snapshot
Synthesis and Immunological Comparison of Differently Linked Lipoarabinomannan Oligosaccharide–Monophosphoryl Lipid A Conjugates as Antituberculosis Vaccines
inferred← citeshttps://doi.org/10.1021/acs.joc.8b00410openalex-snapshot
Stereocontrolled Synthesis of α-Xylofuranosides Using a Conformationally Restricted Donor
inferred← citeshttps://doi.org/10.1021/acscentsci.9b00042openalex-snapshot
Defining the SN1 Side of Glycosylation Reactions: Stereoselectivity of Glycopyranosyl Cations
inferred← citeshttps://doi.org/10.1021/ja072892+openalex-snapshot
Synthesis of the Docosanasaccharide Arabinan Domain of Mycobacterial Arabinogalactan and a Proposed Octadecasaccharide Biosynthetic Precursor
inferred← citeshttps://doi.org/10.1021/ja109932topenalex-snapshot
Synthesis of Docosasaccharide Arabinan Motif of Mycobacterial Cell Wall
inferred← citeshttps://doi.org/10.1021/ja405588xopenalex-snapshot
Probing the Influence of a 4,6-O-Acetal on the Reactivity of Galactopyranosyl Donors: Verification of the Disarming Influence of thetrans–gaucheConformation of C5–C6 Bonds
inferred← citeshttps://doi.org/10.1021/jacs.3c12815openalex-snapshot
One-Pot Assembly of Mannose-Capped Lipoarabinomannan Motifs up to 101-Mer from the Mycobacterium tuberculosis Cell Wall
inferred← citeshttps://doi.org/10.1021/jacsau.5c01069openalex-snapshot
Commonality of Mechanism in Glycoside Hydrolases, Nucleoside Hydrolases, and Phosphorylases: Importance of Side-Chain Conformation Preorganization
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On the Use of 3,5- O -Benzylidene and 3,5- O -(Di- tert -butylsilylene)-2- O -benzylarabinothiofuranosides and Their Sulfoxides as Glycosyl Donors for the Synthesis of β-Arabinofuranosides: Importance of the Activation Method
inferred← citeshttps://doi.org/10.1021/jo100575aopenalex-snapshot
Probing the Effect of Acylation on Arabinofuranose Ring Conformation in Di- and Trisaccharide Fragments of Mycobacterial Arabinogalactan
inferred← citeshttps://doi.org/10.1021/jo2017026openalex-snapshot
Methodology Development and Physical Organic Chemistry: A Powerful Combination for the Advancement of Glycochemistry
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Stereoselective C-Glycoside Formation with 2-O-Benzyl-4,6-O-benzylidene Protected 3-Deoxy Gluco- and Mannopyranoside Donors: Comparison with O-Glycoside Formation
inferred← citeshttps://doi.org/10.1021/jo3014929openalex-snapshot
Stereoselective N-Glycosylation of 2-Deoxythioribosides for Fluorescent Nucleoside Synthesis
inferred← citeshttps://doi.org/10.1021/jo400945jopenalex-snapshot
Nucleophilic Addition to Silyl-Protected Five-Membered Ring Oxocarbenium Ions Governed by Stereoelectronic Effects
inferred← citeshttps://doi.org/10.1021/jo501191bopenalex-snapshot
Synthesis of Oligomers of β- l -Arabinofuranosides of (4R)-4-Hydroxy- l -proline Relevant to the Mugwort Pollen Allergen, Art v 1
inferred← citeshttps://doi.org/10.1021/jo802000popenalex-snapshot
Efficient Chemical Synthesis of a Dodecasaccharidyl Lipomannan Component of Mycobacterial Lipoarabinomannan
inferred← citeshttps://doi.org/10.1021/ol101520qopenalex-snapshot
β-Selective Arabinofuranosylation Using a 2,3-O-Xylylene-Protected Donor
inferred← citeshttps://doi.org/10.1021/ol102112zopenalex-snapshot
Synthesis of a Dimer of β-(1,4)- l -Arabinosyl-(2 S ,4 R )-4-hydroxyproline Inspired by Art v 1, the Major Allergen of Mugwort
inferred← citeshttps://doi.org/10.1021/ol401755eopenalex-snapshot
β-Arabinofuranosylation Using 5-O-(2-Quinolinecarbonyl) Substituted Ethyl Thioglycoside Donors
inferred← citeshttps://doi.org/10.1021/ol4036903openalex-snapshot
Synthesis of a Miniature Lipoarabinomannan
inferred← citeshttps://doi.org/10.1038/ncomms14851openalex-snapshot
Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units
inferred← citeshttps://doi.org/10.1038/s44160-023-00428-xopenalex-snapshot
Synthesis of branched arabinogalactans up to a 140-mer from Panax notoginseng and their anti-pancreatic-cancer activity
inferred← citeshttps://doi.org/10.1039/9781849730891-00038openalex-snapshot
Mycobacterial lipoarabinomannan fragments as haptens for potential anti-tuberculosis vaccines
inferred← citeshttps://doi.org/10.1039/b901499nopenalex-snapshot
Stereoselective synthesis of 1,2-cis-glycosylic linkages
inferred← citeshttps://doi.org/10.1039/c0ob00423eopenalex-snapshot
Synthesis and NMR spectroscopic analysis of acylated pentasaccharide fragments of mycobacterial arabinogalactan
inferred← citeshttps://doi.org/10.1039/c0ob00989jopenalex-snapshot
Synthesis of arabinofuranose branched galactofuran tetrasaccharides, constituents of mycobacterial arabinogalactan
inferred← citeshttps://doi.org/10.1039/c3cc00042gopenalex-snapshot
Automated solid phase synthesis of oligoarabinofuranosides
inferred← citeshttps://doi.org/10.1039/c3ob40958aopenalex-snapshot
Chemical synthesis of β-arabinofuranosyl containing oligosaccharides derived from plant cell wall extensins
inferred← citeshttps://doi.org/10.1039/c3ob41212aopenalex-snapshot
Stereoselective synthesis of Arabidopsis CLAVATA3 (CLV3) glycopeptide, unique protein post-translational modifications of secreted peptide hormone in plant
inferred← citeshttps://doi.org/10.1039/c5sc00280jopenalex-snapshot
Stereocontrolled 1,2-cis glycosylation as the driving force of progress in synthetic carbohydrate chemistry
inferred← citeshttps://doi.org/10.1039/c9md00036dopenalex-snapshot
Novel carbohydrate modified berberine derivatives: synthesis and in vitro anti-diabetic investigation
inferred← citeshttps://doi.org/10.1039/d0ob00260gopenalex-snapshot
β-Selective xylulofuranosylation via a conformationally-restricted glycosyl donor
inferred← citeshttps://doi.org/10.1039/d0qo00704hopenalex-snapshot
Synthesis of an unusual hexasaccharide repeating unit from the cell wall polysaccharide of Eubacterium saburreum strain T19
inferred← citeshttps://doi.org/10.1039/d1qo00203aopenalex-snapshot
Stereoselective synthesis of α- d -fructofuranosides using a 4,6- O -siloxane-protected donor
inferred← citeshttps://doi.org/10.1039/d4sc03449jopenalex-snapshot
Zinc( ii )-mediated stereoselective construction of 1,2- cis 2-azido-2-deoxy glycosidic linkage: assembly of Acinetobacter baumannii K48 capsular pentasaccharide derivative
inferred← citeshttps://doi.org/10.1055/s-0040-1719854openalex-snapshot
Silylated Sugars – Synthesis and Properties
inferred← citeshttps://doi.org/10.1080/07328303.2019.1630839openalex-snapshot
An extensive review of studies on mycobacterium cell wall polysaccharide-related oligosaccharides – part I: Synthetic studies on arabinofuranosyl oligosaccharides
inferred← citeshttps://doi.org/10.1080/07328303.2019.1630841openalex-snapshot
An extensive review of studies on mycobacterium cell wall polysaccharide-related oligosaccharides – part III: synthetic studies and biological applications of arabinofuranosyl oligosaccharides and their analogs, derivatives and conjugates
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Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis
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Synthesis, biological studies of linear and branched arabinofuranoside-containing glycolipids and their interaction with surfactant protein A
inferred← citeshttps://doi.org/10.1515/pac-2023-0112openalex-snapshot
Synthesis and structural analysis of d-fructofuranosylated compounds for the analysis of GH172 difructose dianhydride I synthase/hydrolase
inferred← citeshttps://doi.org/10.2174/0929867326666181126112124openalex-snapshot
Novel Vaccine Candidates against Tuberculosis
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Oligomers of beta-L-arabinosides of hydroxyproline : synthesis of the carbohydrate epitope of the Art v 1 allergen
inferred← citeshttps://doi.org/10.3389/fchem.2022.972429openalex-snapshot
Recent advances in stereoselective 1,2-cis-O-glycosylations
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Protecting Groups in Carbohydrate Chemistry: Influence on Stereoselectivity of Glycosylations
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ZnI2-Mediated cis-Glycosylations of Various Constrained Glycosyl Donors: Recent Advances in cis-Selective Glycosylations
inferred← citeshttps://doi.org/10.3390/molecules30153295openalex-snapshot
A Rational Synthesis of a Branched Decaarabinofuranoside Related to the Fragments of Mycobacterial Polysaccharides
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Silyl-protective groups influencing the reactivity and selectivity in glycosylations
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Progress and challenges in the synthesis of sequence controlled polysaccharides
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Stereoselectivity of D-Psicofuranosylation Influenced by Protecting Groups of Psicofuranosyl Donors
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Development of highly efficient and stereocontrolled O-glycosylation methodologies and its application to the construction of bacterial glycans
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My Stroll in the Backyard of Carbohydrate Chemistry
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Chemical Synthesis of Furanose Glycosides
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Accelerated O-Glycosylation under Frozen Conditions and Its Application to the Synthesis of Complex Glycans
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Intramolecular Aglycon Delivery and Its Application to Stereoselective Synthesis of Glycans
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Encounter with Carbohydrate Chemistry to Amateurish Glycobiology
inferred← citeshttps://doi.org/10.5059/yukigoseikyokaishi.76.59openalex-snapshot
Exploring Future Perspective of Glycochemistry by Japanese Researchers
inferred← citeshttps://doi.org/10.7831/ras.6.1openalex-snapshot
STEREODIRECTING EFFECT OF CYCLIC SILYL PROTECTING GROUPS IN CHEMICAL GLYCOSYLATION
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