Copper(II)‐Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β‐Glycosides of
            <i>N</i>
            ‐Acetylglucosamine

Wittmann, Valentin; Lennartz, Dirk

doi:10.1002/1099-0690(200204)2002:8<1363::aid-ejoc1363>3.0.co;2-#

Cited by 67 publications

(33 citation statements)

References 48 publications

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“…In addition, hydroxybutenyl glycoside 27, obtained by O-deacetylation of compound 26, 43 GlcNAc 28, and allyl 2-acetamido-2-deoxy-b-D D-glucopyranoside 29 were used as monovalent WGA ligands (Scheme 2).…”

Section: Synthesis Of Wga Ligandsmentioning

confidence: 99%

Probing multivalent carbohydrate–lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates

Maierhofer

Rohmer

Wittmann

2007

Bioorganic & Medicinal Chemistry

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Abstract-We report here the synthesis of a series of mono-to trivalent N-acetylglucosamine (GlcNAc) derivatives as ligands for the plant lectin wheat germ agglutinin (WGA). Their WGA binding potencies were determined by an established enzyme-linked lectin assay (ELLA) employing microtiter plates with non-covalently immobilized porcine stomach mucin (PSM) as reference ligand and an ELLA with a new GlcNAc derivative covalently immobilized via a thiourea linkage. Comparison of both assays revealed that the type of presentation of GlcNAc residues on the microtiter plates either as part of a glycoprotein or as a covalently immobilized monosaccharide derivative strongly influences the outcome of the assay. Although the apparent dissociation constants K ELLA D for the interaction of peroxidase-labeled WGA with the microtiter plates are comparable for both surfaces, IC 50 values obtained with the PSM-free ELLA were substantially lower. Even more strikingly, this ELLA displayed a better differentiation between ligands of different valency leading to significantly higher relative inhibitory potencies of multivalent ligands compared to monovalent. Additionally, problems associated with the use of PSM, such as maximum inhibition at considerably less than 100% and poor reproducibility of IC 50 values could be overcome with this type of ELLA.

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Section: Synthesis Of Wga Ligandsmentioning

confidence: 99%

Probing multivalent carbohydrate–lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates

Maierhofer

Rohmer

Wittmann

2007

Bioorganic & Medicinal Chemistry

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“…In the presence of CuX 2 , 2-methyl(tri-O-acetyl--Dglucopyrano)[2,1-d]2-oxazoline 189 reacts with glycosyl acceptors bearing primary or secondary hydroxy groups to yield 2-acetamido derivatives 190 (Scheme 81) [126].…”

Section: Other Copper(ii) Halide-mediated Reactionsmentioning

confidence: 99%

Versatile Reactivity and Catalytic Effects of Copper(II) Halides in Organic Syntheses

Csende¹,

Stájer

2005

COC

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Copper(II) salts are widely applied for the halogenation of aromatic and heteroaromatic systems, the halides. In coupling reactions, CuCl 2 has been used as a catalyst for the benzylation of aromates, the synthesis of alkanes, and the preparation of diacetylenes, cyclohexenones and symmetric biaryls. It has further proved suitable for stereoselective cyclization to lactones, carbon-nitrogen coupling and lactamization, and for the simple preparation of aroylaminohydrazones, the allylic amination of olefins, the carbonylation of alkylamines, and heterocyclizations to pyrrolidinones, pyridinones, pyrroles and dihydrofurans. The dehydrogenation of carbocycles and heterocycles can be used in the synthesis of gibberelic acid, for the aromatization of oestrogen derivatives and for the conversion of dihydrouracils to uracils. From tetrahydroisoquinolines, dihydro derivatives have been formed, while dihydropyridazines in the presence of Cu(II) salts yield pyridazines. Similarly, the oxidations of cyclohexane, adamantane and methylcatechol to benzoquinone, and amines to nitriles have been performed. The conversion of aldehydes to nitriles and benzyl radical cyclizations to butyrolactones have been achieved. Protection and deprotection, and various other Cu(II) halide-mediated reactions are also discussed.

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“…For attachment of the carbohydrates a new urethane-type linker based on the Aloc protecting group has been developed (Scheme 2.7.1) [15,19] (for other linkers used in solid-phase synthesis see Chapter 6.1). In contrast with glycosylation reactions employing solid phase-bound peptides [20], the formation of an urethane bond proceeds in virtually quantitative yield.…”

Section: Design and Synthesis Of A Library Of Cyclic Neoglycopeptidesmentioning

confidence: 99%

“…Synthesis of the activated carbonate 12 for highyield modification of side-chain amino groups of diamino acids [15,19]. Scheme 2.7.2.…”

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Synthetic Approaches to Study Multivalent Carbohydrate—Lectin Interactions

Wittmann

2004

Highlights in Bioorganic Chemistry

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Copper(II)‐Mediated Activation of Sugar Oxazolines: Mild and Efficient Synthesis of β‐Glycosides of N ‐Acetylglucosamine

Cited by 67 publications

References 48 publications

Probing multivalent carbohydrate–lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates

Probing multivalent carbohydrate–lectin interactions by an enzyme-linked lectin assay employing covalently immobilized carbohydrates

Versatile Reactivity and Catalytic Effects of Copper(II) Halides in Organic Syntheses

Synthetic Approaches to Study Multivalent Carbohydrate—Lectin Interactions

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