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Amadori Rearrangement

The Experts below are selected from a list of 258 Experts worldwide ranked by ideXlab platform

Tanja M Wrodnigg – 1st expert on this subject based on the ideXlab platform

  • new lectin ligands testing of Amadori Rearrangement products with a series of mannoside specific lectins
    Carbohydrate Research, 2019
    Co-Authors: Herwig Prasch, Cornelia Hojnik, Thisbe K Lindhorst, Blanka Didak, Ludovic Landemarre, Tanja M Wrodnigg

    Abstract:

    Abstract 1-(N-Phenyl)amino-1-deoxy-α-D-manno-hept-2-ulose (2) and two multivalent BSA-based structures 7 and 8, d -manno-configured C-glycosyl-type compounds derived from an Amadori Rearrangement, were evaluated as ligands for mannoside-specific lectins of various sources. The determination of the concentration corresponding to 50% of inhibition (IC50) is described. Multivalency turned out to effectively influence ligand selectivity and lectin binding.

  • the Amadori Rearrangement for carbohydrate conjugation scope and limitations
    European Journal of Organic Chemistry, 2016
    Co-Authors: Cornelia Hojnik, Anne Muller, Tobiaselias Gloe, Thisbe K Lindhorst, Tanja M Wrodnigg

    Abstract:

    The Amadori Rearrangement was investigated for the synthesis of C-glycosyl-type neoglycoconjugates. Various amines including diamines, amino-functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non-natural C-glycosyl-type glycoconjugates of the d-gluco and d-manno series. With these studies, the scope and limitations of the Amadori Rearrangement as a conjugation method have been exemplified with respect to the carbohydrate substrate, as well as the amino components.

  • Are D-manno-configured Amadori products ligands of the bacterial lectin FimH?
    Beilstein Journal of Organic Chemistry, 2015
    Co-Authors: Tobiaselias Gloe, Cornelia Hojnik, Tanja M Wrodnigg, Insa Stamer, Thisbe K Lindhorst

    Abstract:

    The Amadori Rearrangement was employed for the synthesis of C-glycosyl-type D-mannoside analogues, namely 1-propargylamino- and 1-phenylamino-1-deoxy-α-D-manno-heptopyranose. They were investigated as ligands of type 1-fimbriated E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori Rearrangement products have a limited activity as inhibitors of bacterial adhesion because the β-C-glycosidically linked aglycone considerably hampers complexation within the carbohydrate binding site of the type 1-fimbrial lectin FimH.

Lothar W Kroh – 2nd expert on this subject based on the ideXlab platform

  • simultaneous formation of 3 deoxy d threo hexo 2 ulose and 3 deoxy d erythro hexo 2 ulose during the degradation of d glucose derived Amadori Rearrangement products mechanistic considerations
    Carbohydrate Research, 2018
    Co-Authors: Martin Kaufmann, Clemens Mugge, Sophie Kruger, Lothar W Kroh

    Abstract:

    Abstract Analyzing classical model reaction systems of Amadori Rearrangement products (ARP) it became apparent that the formation of 3-deoxy- d -threo-hexo-2-ulose (3-deoxygalactosone, 3-DGal) during the degradation of ARPs is highly dependent on pH and the amino acid residue of the respective ARP. Based on a detailed analysis of the NMR chemical shifts of the sugar moieties of different ARPs, it could be derived that the formation of 3-DGal is sensitive to the stability of a co-operative hydrogen bond network which involves HO-C3, the deprotonated carboxyl functionality and the protonated amino nitrogen of the amino acid substituent. Participating in this bond network, HO-C3 is partially protonated which facilitates the elimination of water at C3. Based on that, a new mechanism of 3-deoxyglycosone formation is proposed.

  • structure reactivity relationship of Amadori Rearrangement products compared to related ketoses
    Carbohydrate Research, 2016
    Co-Authors: Martin Kaufmann, Philipp M Meissner, Daniel Pelke, Clemens Mugge, Lothar W Kroh

    Abstract:

    Structure-reactivity relationships of Amadori Rearrangement products compared to their related ketoses were derived from multiple NMR spectroscopic techniques. Besides structure elucidation of six Amadori Rearrangement products derived from d-glucose and d-galactose with l-alanine, l-phenylalanine and l-proline, especially quantitative (13)C selective saturation transfer NMR spectroscopy was applied to deduce information on isomeric systems. It could be shown exemplarily that the Amadori compound N-(1-deoxy-d-fructos-1-yl)-l-proline exhibits much higher isomerisation rates than d-fructose, which can be explained by C-1 substituent mediated intramolecular catalysis. In combination with a reduced carbonyl activity of Amadori compounds compared to their related ketoses which results in an increased acyclic keto isomer concentration, the results on isomerisation dynamics lead to a highly significant increased reactivity of Amadori compounds. This can be clearly seen, comparing approximated carbohydrate milieu stability time constants (ACuSTiC) which is 1 s for N-(1-deoxy-d-fructos-1-yl)-l-proline and 10 s for d-fructose at pD 4.20 ± 0.05 at 350 K. In addition, first NMR spectroscopic data are provided, which prove that α-pyranose of (amino acid substituted) d-fructose adopts both, (2)C5 and (5)C2 conformation.

  • Structure–reactivity relationship of Amadori Rearrangement products compared to related ketoses
    Carbohydrate Research, 2016
    Co-Authors: Martin Kaufmann, Philipp M Meissner, Daniel Pelke, Clemens Mugge, Lothar W Kroh

    Abstract:

    Abstract Structure-reactivity relationships of Amadori Rearrangement products compared to their related ketoses were derived from multiple NMR spectroscopic techniques. Besides structure elucidation of six Amadori Rearrangement products derived from d -glucose and d -galactose with l -alanine, l -phenylalanine and l -proline, especially quantitative 13C selective saturation transfer NMR spectroscopy was applied to deduce information on isomeric systems. It could be shown exemplarily that the Amadori compound N-(1-deoxy- d -fructos-1-yl)- l -proline exhibits much higher isomerisation rates than d -fructose, which can be explained by C-1 substituent mediated intramolecular catalysis. In combination with a reduced carbonyl activity of Amadori compounds compared to their related ketoses which results in an increased acyclic keto isomer concentration, the results on isomerisation dynamics lead to a highly significant increased reactivity of Amadori compounds. This can be clearly seen, comparing approximated carbohydrate milieu stability time constants (ACuSTiC) which is 1 s for N-(1-deoxy- d -fructos-1-yl)- l -proline and 10 s for d -fructose at pD 4.20 ± 0.05 at 350 K. In addition, first NMR spectroscopic data are provided, which prove that α-pyranose of (amino acid substituted) d -fructose adopts both, 2C5 and 5C2 conformation.

Martin Kaufmann – 3rd expert on this subject based on the ideXlab platform

  • simultaneous formation of 3 deoxy d threo hexo 2 ulose and 3 deoxy d erythro hexo 2 ulose during the degradation of d glucose derived Amadori Rearrangement products mechanistic considerations
    Carbohydrate Research, 2018
    Co-Authors: Martin Kaufmann, Clemens Mugge, Sophie Kruger, Lothar W Kroh

    Abstract:

    Abstract Analyzing classical model reaction systems of Amadori Rearrangement products (ARP) it became apparent that the formation of 3-deoxy- d -threo-hexo-2-ulose (3-deoxygalactosone, 3-DGal) during the degradation of ARPs is highly dependent on pH and the amino acid residue of the respective ARP. Based on a detailed analysis of the NMR chemical shifts of the sugar moieties of different ARPs, it could be derived that the formation of 3-DGal is sensitive to the stability of a co-operative hydrogen bond network which involves HO-C3, the deprotonated carboxyl functionality and the protonated amino nitrogen of the amino acid substituent. Participating in this bond network, HO-C3 is partially protonated which facilitates the elimination of water at C3. Based on that, a new mechanism of 3-deoxyglycosone formation is proposed.

  • structure reactivity relationship of Amadori Rearrangement products compared to related ketoses
    Carbohydrate Research, 2016
    Co-Authors: Martin Kaufmann, Philipp M Meissner, Daniel Pelke, Clemens Mugge, Lothar W Kroh

    Abstract:

    Structure-reactivity relationships of Amadori Rearrangement products compared to their related ketoses were derived from multiple NMR spectroscopic techniques. Besides structure elucidation of six Amadori Rearrangement products derived from d-glucose and d-galactose with l-alanine, l-phenylalanine and l-proline, especially quantitative (13)C selective saturation transfer NMR spectroscopy was applied to deduce information on isomeric systems. It could be shown exemplarily that the Amadori compound N-(1-deoxy-d-fructos-1-yl)-l-proline exhibits much higher isomerisation rates than d-fructose, which can be explained by C-1 substituent mediated intramolecular catalysis. In combination with a reduced carbonyl activity of Amadori compounds compared to their related ketoses which results in an increased acyclic keto isomer concentration, the results on isomerisation dynamics lead to a highly significant increased reactivity of Amadori compounds. This can be clearly seen, comparing approximated carbohydrate milieu stability time constants (ACuSTiC) which is 1 s for N-(1-deoxy-d-fructos-1-yl)-l-proline and 10 s for d-fructose at pD 4.20 ± 0.05 at 350 K. In addition, first NMR spectroscopic data are provided, which prove that α-pyranose of (amino acid substituted) d-fructose adopts both, (2)C5 and (5)C2 conformation.

  • Structure–reactivity relationship of Amadori Rearrangement products compared to related ketoses
    Carbohydrate Research, 2016
    Co-Authors: Martin Kaufmann, Philipp M Meissner, Daniel Pelke, Clemens Mugge, Lothar W Kroh

    Abstract:

    Abstract Structure-reactivity relationships of Amadori Rearrangement products compared to their related ketoses were derived from multiple NMR spectroscopic techniques. Besides structure elucidation of six Amadori Rearrangement products derived from d -glucose and d -galactose with l -alanine, l -phenylalanine and l -proline, especially quantitative 13C selective saturation transfer NMR spectroscopy was applied to deduce information on isomeric systems. It could be shown exemplarily that the Amadori compound N-(1-deoxy- d -fructos-1-yl)- l -proline exhibits much higher isomerisation rates than d -fructose, which can be explained by C-1 substituent mediated intramolecular catalysis. In combination with a reduced carbonyl activity of Amadori compounds compared to their related ketoses which results in an increased acyclic keto isomer concentration, the results on isomerisation dynamics lead to a highly significant increased reactivity of Amadori compounds. This can be clearly seen, comparing approximated carbohydrate milieu stability time constants (ACuSTiC) which is 1 s for N-(1-deoxy- d -fructos-1-yl)- l -proline and 10 s for d -fructose at pD 4.20 ± 0.05 at 350 K. In addition, first NMR spectroscopic data are provided, which prove that α-pyranose of (amino acid substituted) d -fructose adopts both, 2C5 and 5C2 conformation.