Martin D. Witte
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View article: Identification of Methylglyoxal Reactive Proteins with Photocaged Glycating Agents
Identification of Methylglyoxal Reactive Proteins with Photocaged Glycating Agents Open
Methylglyoxal is a highly reactive metabolite that is formed spontaneously in the glycolytic pathway. The side chains of various amino acid residues react with methylglyoxal to form advanced‐glycation end products (AGEs). This enzyme‐indep…
View article: A Purification‐Free Strategy for the Electrochemical Oxidation of the Primary Hydroxy Group in Glycopyranosides
A Purification‐Free Strategy for the Electrochemical Oxidation of the Primary Hydroxy Group in Glycopyranosides Open
An operationally simple protocol for the electrochemical oxidation of the primary hydroxy group in glycopyranosides is presented. The strategy uses aqueous ammonia as a base and electrolyte, reticulated vitreous carbon (RVC) electrodes, an…
View article: The Synthesis of Aryl‐β‐<i>C</i>‐Glycosides from Native Saccharides
The Synthesis of Aryl‐β‐<i>C</i>‐Glycosides from Native Saccharides Open
The synthesis of p ‐nitrophenol‐β‐ C ‐glycosides from native mono‐, di‐, and trisaccharides is described. The one‐pot‐two‐step procedure uses water as the solvent and produces exclusively β‐ C ‐glycosides, the desired stereochemistry for m…
View article: Electrochemical Ammoxidation of Unprotected Glycosides
Electrochemical Ammoxidation of Unprotected Glycosides Open
Cyano-sugars are useful carbohydrate building blocks. Here, we report an electrocatalytic method to oxidize the primary alcohols of unprotected glycosides to the corresponding nitrile using 2,2,6,6-tetramethylpiperidin-1-oxyl (TEMPO) as a …
View article: Ammoxidation of Unprotected Glycosides: A One‐Pot Conversion of Alcohols to Nitriles
Ammoxidation of Unprotected Glycosides: A One‐Pot Conversion of Alcohols to Nitriles Open
Functionalized carbohydrates are important in various fields, but protection‐free selective functionalization often remains challenging. We demonstrate that the primary hydroxy group in minimally protected carbohydrates can be directly con…
View article: Ammoxidation of Unprotected Glycosides: A One-Pot Conversion of Alcohols to Nitriles
Ammoxidation of Unprotected Glycosides: A One-Pot Conversion of Alcohols to Nitriles Open
Functionalized carbohydrates are important in various fields, but protection-free selective functionalization often remains chal-lenging. We demonstrate that the primary hydroxy group in minimally protected carbohydrates can be directly co…
View article: Synthesis of deoxypropionates using a combination of enzymatic desymmetrisation and substrate controlled conjugate addition
Synthesis of deoxypropionates using a combination of enzymatic desymmetrisation and substrate controlled conjugate addition Open
The all -syn deoxypropionate motif can be efficiently constructed using a combination of enzymatic desymmetrization and substrate-controlled conjugate addition of lithium dimethylcopper. This strategy was used to prepare mycocerosic acid, …
View article: Site‐Selective Palladium‐catalyzed Oxidation of Unprotected Aminoglycosides and Sugar Phosphates
Site‐Selective Palladium‐catalyzed Oxidation of Unprotected Aminoglycosides and Sugar Phosphates Open
The site‐selective modification of complex biomolecules by transition metal‐catalysis is highly warranted, but often thwarted by the presence of Lewis basic functional groups. This study demonstrates that protonation of amines and phosphat…
View article: Regioselective palladium-catalysed aerobic oxidation of dextran and its use as a bio-based binder in paperboard coatings
Regioselective palladium-catalysed aerobic oxidation of dextran and its use as a bio-based binder in paperboard coatings Open
Dextran can be selectively oxidized at the C3-position and subsequently crosslinked with dihydrazides.
View article: Total synthesis of dissectol A, using an enediolate-based Tsuji–Trost reaction
Total synthesis of dissectol A, using an enediolate-based Tsuji–Trost reaction Open
The densely functionalized terpene glycoside dissectol A has been prepared via site-selective oxidation and an intramolecular Tsuji–Trost allylic alkylation reaction with an enediolate as the nucleophile.
View article: Practical Site-selective Oxidation of Glycosides with Pd(OAc)2/Neocuproine
Practical Site-selective Oxidation of Glycosides with Pd(OAc)2/Neocuproine Open
Palladium-catalyzed oxidation of the secondary C3 hydroxy group in glycopyranosides has set its mark in the selective modification of unprotected carbohydrates. The pre-formed catalyst [(neocuproine)PdOAc]2(OTf)2 oxidizes besides monosacch…
View article: PGL-III, a Rare Intermediate of <i>Mycobacterium leprae</i> Phenolic Glycolipid Biosynthesis, Is a Potent Mincle Ligand
PGL-III, a Rare Intermediate of <i>Mycobacterium leprae</i> Phenolic Glycolipid Biosynthesis, Is a Potent Mincle Ligand Open
Although leprosy (Hansen's disease) is one of the oldest known diseases, the pathogenicity of Mycobacterium leprae (M. leprae) remains enigmatic. Indeed, the cell wall components responsible for the immune response against M. leprae are as…
View article: A Predictive Model for the Pd‐Catalyzed Site‐Selective Oxidation of Diols
A Predictive Model for the Pd‐Catalyzed Site‐Selective Oxidation of Diols Open
A predictive model, shaped as a set of rules, is presented that predicts site‐selectivity in the mono‐oxidation of diols by palladium‐neocuproine catalysis. For this, the factors that govern this site‐selectivity within diols and between d…
View article: CCDC 2158399: Experimental Crystal Structure Determination
CCDC 2158399: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158470: Experimental Crystal Structure Determination
CCDC 2158470: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158739: Experimental Crystal Structure Determination
CCDC 2158739: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158390: Experimental Crystal Structure Determination
CCDC 2158390: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158736: Experimental Crystal Structure Determination
CCDC 2158736: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158467: Experimental Crystal Structure Determination
CCDC 2158467: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158452: Experimental Crystal Structure Determination
CCDC 2158452: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158464: Experimental Crystal Structure Determination
CCDC 2158464: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: CCDC 2158459: Experimental Crystal Structure Determination
CCDC 2158459: Experimental Crystal Structure Determination Open
An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available …
View article: Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates
Synthesis of Methylene Tetrahydrofurane‐Fused Carbohydrates Open
A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether function…
View article: Site-Selective Electrochemical Oxidation of Glycosides
Site-Selective Electrochemical Oxidation of Glycosides Open
Quinuclidine-mediated electrochemical oxidation of glycopyranosides provides C3-ketosaccharides with high selectivity and good yields. The method is a versatile alternative to Pd-catalyzed or photochemical oxidation and is complementary to…
View article: Site-selective introduction of thiols in unprotected glycosides
Site-selective introduction of thiols in unprotected glycosides Open
Site-selective oxidation of unprotected saccharides, followed by treatment of the corresponding trityl hydrazone with t -Bu hypochlorite, gives a chloro-azo intermediate that can be substituted to give deoxythio sugars. This allows a prote…
View article: The linkage-type and the exchange molecule affect the protein-labeling efficiency of iminoboronate probes
The linkage-type and the exchange molecule affect the protein-labeling efficiency of iminoboronate probes Open
Acyl hydrazides are the most suitable substrates for the synthesis of iminoboronate probes. They have the appropriate balance between stability, which is required for targeting, and reversibility, which is required for detecting the labele…
View article: Site-Selective Modification of (Oligo)Saccharides
Site-Selective Modification of (Oligo)Saccharides Open
Oligosaccharides, either as such or as part of glycolipids, glycopeptides, or glycoproteins, are ubiquitous in nature and fulfill important roles in the living cell. Also in medicine and to some extent in materials, oligosaccharides play a…
View article: Site-selective Electrochemical Oxidation of Glucosides
Site-selective Electrochemical Oxidation of Glucosides Open
Quinuclidine-mediated electrochemical oxidation of glycopyranosides provides C3-ketosaccharides with excellent selectivity. The method is a versatile alternative to Pd-catalyzed oxidation, and to photochemical oxidation, and is complementa…
View article: Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides
Site-Selective Dehydroxy-Chlorination of Secondary Alcohols in Unprotected Glycosides Open
To circumvent protecting groups, the site-selective modification of unprotected glycosides is intensively studied. We show that site-selective oxidation, followed by treatment of the corresponding trityl hydrazone with tert-butyl hypochlor…
View article: Palladium‐Catalyzed Oxidation of Glucose in Glycopeptides**
Palladium‐Catalyzed Oxidation of Glucose in Glycopeptides** Open
Selective modification of carbohydrate residues in glycopeptides is highly relevant as a tool in glycobiology. In particular, oxidation allows for subsequent ligation with a label or handle and can be effectuated enzymatically or chemicall…