Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

Neumann, Janna; Weingarten, Saskia; Thiem, Joachim

doi:10.1002/ejoc.200600958

Cited by 34 publications

(16 citation statements)

References 42 publications

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“…The synthesis of aldehyde 2 (Scheme 1) was adapted from an elegant published procedure based on Dess-Martin oxidation. [14] NMR spectroscopy confirmed the formation of the required aldehyde together with its hydrated form (geminal diol). Upon standing in anhydrous solution (DMSO), a gradual dehydration of the diol was observed, which is in agreement with the literature.…”

Section: Resultsmentioning

confidence: 82%

Charged Hexosaminides as New Substrates for β‐N‐Acetylhexosaminidase‐Catalyzed Synthesis of Immunomodulatory Disaccharides

et al. 2011

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This work is a structure-activity relationship study that investigates the influence of the nature and amount of negative charge in carbohydrate substrates on the affinity of b-N-acetylhexos-A C H T U N G T R E N N U N G aminidases, and on the stimulation of natural killer cells. It describes synthetic procedures yielding novel glycosides that are useful in immunoactivation. Specifically, we present a thorough study on the ability of six C-6 modified b-N-acetylhexosaminides (aldehyde, uronate, 6-O-sulfate, 6-O-phosphate) to serve as substrates for cleavage and glycosylation by a library of b-N-acetylhexosaminidases from various sources. Four novel disaccharides with one or two (negatively) charged groups were prepared in synthetic reactions in good yields. Surprisingly, the 6-Ophosphorylated substrate, although cleaved by a number of enzymes from the series, worked neither as a donor nor as an acceptor in transglycosylation reactions. The results of wet experiments were supported by molecular modeling of substrates in the active site of two representative enzymes from the screening. All ten prepared compounds were examined in terms of their immunoactivity, namely as ligands of two activation receptors of natural killer (NK) cells, NKR-P1 and CD69, both with isolated proteins and whole cells. Sulfated disaccharides in particular acted as very efficient protectants of NK cells against activation-induced apoptosis, and as stimulants of the natural killing of resistant tumor cells, which makes them good candidates for potential clinical use in cancer treatment.

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Section: Resultsmentioning

confidence: 82%

Charged Hexosaminides as New Substrates for β‐N‐Acetylhexosaminidase‐Catalyzed Synthesis of Immunomodulatory Disaccharides

et al. 2011

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“…As previously described [17] Dess-Martin oxidation is a mild and selective method to obtain 6-carbaldehydes from unprotected glycosides, however, the yields could not be enhanced to more than 50 % (Scheme 1).…”

Section: Oxidationmentioning

confidence: 93%

“…[17] The 2,6-Nlinked structures 37-40 (Scheme 5) could be obtained in average to good yields without attempts for optimization.…”

Section: Reductive Aminationmentioning

confidence: 99%

“…Then the catalyst was filtered through sodium sulfate and the filtrate was concentrated. (90.7 mg, 0.229 mmol) in methanol (2 mL) and amine 36 [17] (114 mg, 0.569 mmol) in methanol (1 mL) were treated according to general procedure 2. After purification by gel permeation chromatography on Sephadex LH20 (methanol/water .506 mmol) was dissolved in methanol (2.5 mL) and amine 36 [17] in methanol (1.5 mL) was added.…”

Section: 4-diamino-15-anhydro-24-dideoxy-d-galactitol (35)mentioning

confidence: 99%

“…(90.7 mg, 0.229 mmol) in methanol (2 mL) and amine 36 [17] (114 mg, 0.569 mmol) in methanol (1 mL) were treated according to general procedure 2. After purification by gel permeation chromatography on Sephadex LH20 (methanol/water .506 mmol) was dissolved in methanol (2.5 mL) and amine 36 [17] in methanol (1.5 mL) was added. The reaction mixture was treated according to general procedure 2 and the residue was purified by gel permeation chromatography (methanol/water, 1:1).…”

Section: 4-diamino-15-anhydro-24-dideoxy-d-galactitol (35)mentioning

confidence: 99%

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Synthesis of Amino‐Bridged Oligosaccharide Mimetics

Neumann

Thiem

2010

Eur J Org Chem

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Synthesis of amino-bridged oligosaccharides using reductive amination opens rapid access to novel glycomimetic target structures as potential ligands for the receptor protein NKR P1 of natural killer cells. Emphasis was laid on fast and facile synthetic routes. The carbonyl building blocks were easily obtained by oxidation with Dess-Martin periodinane or iodoxybenzoic acid (IBX). For the required amino-function-

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Stereodivergente De‐novo‐Synthese verzweigter Aminozucker durch Lewis‐Säure‐induzierte Umlagerung von 1,2‐Oxazinen

2009

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Gut getarnt: 1,2‐Oxazine wie 1 lagern unter Einwirkung von Lewis‐Säuren in bicyclische Produkte vom Typ 2 um, die als geschützte Äquivalente von Aminozuckern in Oligosaccharide eingebaut werden können. Nachfolgende reduktive Schritte erzeugen ungewöhnliche Oligosaccharide 3 mit C‐2‐verzweigten 4‐Aminozuckereinheiten. Die meisten Reaktionen erfolgen unter exzellenter Stereokontrolle und ermöglichen die Synthese einer Kollektion von Stereoisomeren.magnified image

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Synthesis of Novel Di‐ and Trisaccharide Mimetics with Non‐Glycosidic Amino Bridges

Cited by 34 publications

References 42 publications

Charged Hexosaminides as New Substrates for β‐N‐Acetylhexosaminidase‐Catalyzed Synthesis of Immunomodulatory Disaccharides

Charged Hexosaminides as New Substrates for β‐N‐Acetylhexosaminidase‐Catalyzed Synthesis of Immunomodulatory Disaccharides

Synthesis of Amino‐Bridged Oligosaccharide Mimetics

Stereodivergente De‐novo‐Synthese verzweigter Aminozucker durch Lewis‐Säure‐induzierte Umlagerung von 1,2‐Oxazinen

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