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The rate and evenness of the substitutions on hyaluronan grafted by dodecanoic acid influenced by the mixed-solvent composition

The result's identifiers

  • Result code in IS VaVaI

    <a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F60917431%3A_____%2F21%3AN0000002" target="_blank" >RIV/60917431:_____/21:N0000002 - isvavai.cz</a>

  • Alternative codes found

    RIV/00216208:11310/21:10438607 RIV/70883521:28110/21:63539062

  • Result on the web

    <a href="https://doi.org/10.1016/j.ijbiomac.2021.08.137" target="_blank" >https://doi.org/10.1016/j.ijbiomac.2021.08.137</a>

  • DOI - Digital Object Identifier

    <a href="http://dx.doi.org/10.1016/j.ijbiomac.2021.08.137" target="_blank" >10.1016/j.ijbiomac.2021.08.137</a>

Alternative languages

  • Result language

    angličtina

  • Original language name

    The rate and evenness of the substitutions on hyaluronan grafted by dodecanoic acid influenced by the mixed-solvent composition

  • Original language description

    In this work, low molecular weight (17 kDa) hyaluronan was modified by dodecanoyl substituents. The activation of dodecanoic acid was mediated by benzoyl chloride towards the preparation of a mixed anhydride, which reacts in a second step with HA in water mixed with an organic solvent. The effect of the cosolvent was studied and showed an even distribution of substituents and higher reaction rate in water: 1,4-dioxane compared to water:tert-butanol where substituents occupy adjacent positions. The chemical characterization of the prepared derivatives was elucidated by NMR, FTIR spectroscopy, thermal analyses, and gas chromatography, while the distribution of substituents was evaluated by enzymatic degradation. Molecular-dynamics simulations reveal opposite solvent separations around HA and dodecanoyl chains, that is stronger in water:tert-butanol solution. The resulting incompatibility of solvation-shells of the two entities repels the reaction intermediates from the HA chain and drives them towards the already bound substituents, explaining the observed differences in the distribution evenness. Thus, the influence of the solvent on the reaction selectivity is observed by shielding reactive sites around HA. Therefore, a control of the distribution of the substituents was obtained by defining the concentration of HA and used cosolvent.

  • Czech name

  • Czech description

Classification

  • Type

    J<sub>SC</sub> - Article in a specialist periodical, which is included in the SCOPUS database

  • CEP classification

  • OECD FORD branch

    10401 - Organic chemistry

Result continuities

  • Project

    <a href="/en/project/FW01010060" target="_blank" >FW01010060: Research and development of pharmaceutical ingredient to artificial tears for the treatment of dry eye syndrome</a><br>

  • Continuities

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

Others

  • Publication year

    2021

  • Confidentiality

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

Data specific for result type

  • Name of the periodical

    International Journal of Biological Macromolecules

  • ISSN

    0141-8130

  • e-ISSN

    0141-8130

  • Volume of the periodical

    189

  • Issue of the periodical within the volume

    31.10.2021

  • Country of publishing house

    NL - THE KINGDOM OF THE NETHERLANDS

  • Number of pages

    11

  • Pages from-to

    826-836

  • UT code for WoS article

  • EID of the result in the Scopus database

    2-s2.0-85113981072