Search Results - "van Rijssel, Erwin R"
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Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates
Published in Chemistry : a European journal (23-05-2019)“…The 3D shape of glycosyl oxocarbenium ions determines their stability and reactivity and the stereochemical course of SN1 reactions taking place on these…”
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Synthesis and Evaluation of Hybrid Structures Composed of Two Glucosylceramide Synthase Inhibitors
Published in ChemMedChem (01-12-2015)“…Glucosylceramide metabolism and the enzymes involved have attracted significant interest in medicinal chemistry, because aberrations in the levels of…”
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3
Furanosyl Oxocarbenium Ion Stability and Stereoselectivity
Published in Angewandte Chemie International Edition (22-09-2014)“…Lewis acid mediated substitution reactions using [D]triethylsilane as a nucleophile at the anomeric center of the four pentofuranoses, ribose, arabinose,…”
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Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing α-L-Guluronic Acid and β-D-Mannuronic Acid
Published in Angewandte Chemie International Edition (22-06-2015)“…The total synthesis of mixed‐sequence alginate oligosaccharides, featuring both β‐D‐mannuronic acid (M) and α‐L‐guluronic acid (G), is reported for the first…”
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Conformational Behaviour of Azasugars Based on Mannuronic Acid
Published in Chembiochem : a European journal of chemical biology (04-07-2017)“…A set of mannuronic‐acid‐based iminosugars, consisting of the C‐5‐carboxylic acid, methyl ester and amide analogues of 1deoxymannorjirimicin (DMJ), was…”
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Manno-epi-cyclophellitols Enable Activity-Based Protein Profiling of Human α‑Mannosidases and Discovery of New Golgi Mannosidase II Inhibitors
Published in Journal of the American Chemical Society (29-07-2020)“…Golgi mannosidase II (GMII) catalyzes the sequential hydrolysis of two mannosyl residues from GlcNAcMan5GlcNAc2 to produce GlcNAcMan3GlcNAc2, the precursor for…”
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Synthesis, Reactivity, and Stereoselectivity of 4‑Thiofuranosides
Published in Journal of organic chemistry (01-02-2019)“…Thiosugars, sugars that have their endocyclic oxygen substituted for a sulfur atom, have been used as stable bioisosteres of naturally occurring glycans…”
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Carba-cyclophellitols Are Neutral Retaining-Glucosidase Inhibitors
Published in Journal of the American Chemical Society (17-05-2017)“…The conformational analysis of glycosidases affords a route to their specific inhibition through transition-state mimicry. Inspired by the rapid reaction rates…”
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Stereoselectivity in the Lewis Acid Mediated Reduction of Ketofuranoses
Published in Journal of organic chemistry (01-05-2015)“…The Lewis acid mediated reduction of ribose-, arabinose-, xylose-, and lyxose-derived methyl and phenyl ketofuranoses with triethylsilane as nucleophile was…”
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Potent and Selective Activity-Based Probes for GH27 Human Retaining α‑Galactosidases
Published in Journal of the American Chemical Society (20-08-2014)“…Lysosomal degradation of glycosphingolipids is mediated by the consecutive action of several glycosidases. Malfunctioning of one of these hydrolases can lead…”
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On the Reactivity of Gulose and Guluronic Acid Building Blocks in the Context of Alginate Assembly
Published in European Journal of Organic Chemistry (01-05-2016)“…A novel set of L‐gulose and L‐guluronic acid building blocks, comprising both monosaccharide and disaccharide synthons, was assembled to investigate how…”
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Chiral Pyrroline-Based Ugi-Three-Component Reactions Are under Kinetic Control
Published in Organic letters (21-06-2013)“…Although it is often assumed that the stereochemistry in Ugi multicomponent reactions is determined in the final Mumm rearrangement step, experimental and…”
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Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing [alpha]-L-Guluronic Acid and [beta]-D-Mannuronic Acid
Published in Angewandte Chemie International Edition (22-06-2015)“…The total synthesis of mixed-sequence alginate oligosaccharides, featuring both [beta]-D-mannuronic acid (M) and [alpha]-L-guluronic acid (G), is reported for…”
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Cover Feature: Furanosyl Oxocarbenium Ion Conformational Energy Landscape Maps as a Tool to Study the Glycosylation Stereoselectivity of 2‐Azidofuranoses, 2‐Fluorofuranoses and Methyl Furanosyl Uronates (Chem. Eur. J. 29/2019)
Published in Chemistry : a European journal (23-05-2019)“…Energy maps of the full conformational space of 5‐membered ring glycosyl oxocarbenium ions have been generated to probe the stereoelectronic effects of…”
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Synthesis of α- and β-Galactopyranose-Configured Isomers of Cyclophellitol and Cyclophellitol Aziridine
Published in European journal of organic chemistry (01-09-2014)“…Cyclophellitol and cyclophellitol aziridine are potent and irreversible mechanism‐based inhibitors of retaining β‐glucosidases. Alterations in the…”
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Synthesis of [alpha]- and [beta]-Galactopyranose-Configured Isomers of Cyclophellitol and Cyclophellitol Aziridine
Published in European journal of organic chemistry (01-09-2014)“…Cyclophellitol and cyclophellitol aziridine are potent and irreversible mechanism-based inhibitors of retaining [beta]-glucosidases. Alterations in the…”
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17
Acceptor Reactivity in the Total Synthesis of Alginate Fragments Containing α-L-Guluronic Acid and β-D-Mannuronic Acid
Published in Angewandte Chemie (22-06-2015)“…The total synthesis of mixed‐sequence alginate oligosaccharides, featuring both β‐D‐mannuronic acid (M) and α‐L‐guluronic acid (G), is reported for the first…”
Get full text
Journal Article -
18
Furanosyl Oxocarbenium Ion Stability and Stereoselectivity
Published in Angewandte Chemie (22-09-2014)“…Lewis acid mediated substitution reactions using [D]triethylsilane as a nucleophile at the anomeric center of the four pentofuranoses, ribose, arabinose,…”
Get full text
Journal Article