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Chemo-Enzymatic Synthesis of Branched N-Acetyllactosamine Glycan Oligomers for Galectin-3 Inhibition

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F61388971%3A_____%2F17%3A00483762" target="_blank" >RIV/61388971:_____/17:00483762 - isvavai.cz</a>

  • Result on the web

    <a href="http://dx.doi.org/10.1002/adsc.201700969" target="_blank" >http://dx.doi.org/10.1002/adsc.201700969</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1002/adsc.201700969" target="_blank" >10.1002/adsc.201700969</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    Chemo-Enzymatic Synthesis of Branched N-Acetyllactosamine Glycan Oligomers for Galectin-3 Inhibition

  • Original language description

    We present here a novel concept for the synthesis of branched N-acetyllactosamine (LacNAc) glycan structures. Through a combination of sequential enzymatic and chemical reactions of Leloir-glycosyltransferases, galactose oxidase and reductive amination, we obtained branched glycan oligomers with a variation of LacNAc and/or N',N ''-diacetyllactosamine (LacdiNAc) glycan epitopes. Incorporation of a branching point was accomplished by an optimized galactose oxidase protocol rendering the C-6 aldehyde functionality at the terminal galactose of a LacNAc oligomer. After glycan chain elongation by glycosyltransferases, the C-6 aldehyde-containing linear building block was conjugated with amine-linker functionalized glycans. Methanol and a temperature of 50 degrees C were found to be optimum conditions for the alpha-picoline borane-catalyzed reductive amination. Chemically branched glycans were obtained in high synthetic yields (approximate to 81%) in preparative batches. Product isolation was accomplished by preparative HPLC with good overall yields (>60%). The structural integrity was proven by ESI-MS and NMR. The herein synthesized branched LacNAc oligomers feature a variation of Lac(di)NAc epitopes and were confirmed to be potent inhibitors of human galectin-3 (Gal-3). The branched decasaccharide with two LacdiNAc-LacNAc branches ranks among the most potent poly-LacNAc-based Gal-3 inhibitors so far.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>imp</sub> - Article in a specialist periodical, which is included in the Web of Science database

  • CEP classification

  • OECD FORD branch

    10608 - Biochemistry and molecular biology

Result continuities

  • Project

    Result was created during the realization of more than one project. More information in the Projects tab.

  • Continuities

    P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Others

  • Publication year

    2017

  • Confidentiality

    S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Data specific for result type

  • Name of the periodical

    Advanced Synthesis & Catalysis

  • ISSN

    1615-4150

  • e-ISSN

  • Volume of the periodical

    359

  • Issue of the periodical within the volume

    22

  • Country of publishing house

    DE - GERMANY

  • Number of pages

    10

  • Pages from-to

    4015-4024

  • UT code for WoS article

    000416166300022

  • EID of the result in the Scopus database

    2-s2.0-85034115972