Mechanism of sulfonation-induced chain scission of selectively
oxidized polysaccharides

J 2020

Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides

MUNSTER, L., B. HANULIKOVA, M. MACHOVSKY, F. LATECKA, I. KURITKA et. al.

Základní údaje

Originální název

Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides

Autoři

MUNSTER, L., B. HANULIKOVA, M. MACHOVSKY, F. LATECKA, I. KURITKA a J. VICHA

Vydání

Carbohydrate Polymers, Oxford, ELSEVIER SCI LTD, 2020, 0144-8617

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10400 1.4 Chemical sciences

Stát vydavatele

Velká Británie a Severní Irsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 9.381

Kód RIV

RIV/00216224:14740/20:00121454

Organizační jednotka

Středoevropský technologický institut

DOI

http://dx.doi.org/10.1016/j.carbpol.2019.115503

UT WoS

000501796600076

Klíčová slova anglicky

Selective oxidation; 23-Dialdehydedextrin; 23-Dialdehydecellulose; Sulfamic acid; 23-Dicarboxydextrin; 23-Dicarboxycellulose

Štítky

ne MU, rivok

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 29. 4. 2021 13:19, Mgr. Pavla Foltynová, Ph.D.

Anotace

V originále

Oxidation of polysaccharides to 2,3-dicarboxypolysaccharides is a two-stage process, where selective oxidation by periodate is followed by secondary oxidation by chlorite. Addition of sulfamic acid before the secondary oxidation influences the molecular weight and degree of oxidation of the product. Here, mechanism of sulfamic acid-catalysed chain scission is elucidated for selectively oxidized cellulose and dextrin. Initially, sulfamic acid sulfonates the aldehyde groups of 2,3-dialdehydepolysaccharide. Introduced -SO3H groups are in ideal position to protonate the oxygen atom of 1-4' glycosidic bond and to trigger acidic hydrolysis. This can be used to obtain a direct control over the molecular weight of the product. Observed slightly lower degree of oxidation was ascribed to the ability of sulfamic acid to scavenge the hypochlorite and thus protect the intermolecular hemiacetals from oxidation. Usually undesirable hypochlorite thus seems to be necessary for preparation of selectively oxidized polysaccharides with degree of oxidation above 90%.

Návaznosti

90043, velká výzkumná infrastruktura

Název: CIISB

90085, velká výzkumná infrastruktura

Název: CERIT-SC

Citovat

MUNSTER, L., B. HANULIKOVA, M. MACHOVSKY, F. LATECKA, I. KURITKA a J. VICHA. Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides. Carbohydrate Polymers. Oxford: ELSEVIER SCI LTD, 2020, roč. 229, FEB, s. 115503-115512. ISSN 0144-8617. Dostupné z: https://dx.doi.org/10.1016/j.carbpol.2019.115503.

@article{1762520,
   author = {Munster, L. and Hanulikova, B. and Machovsky, M. and Latecka, F. and Kuritka, I. and Vicha, J.},
   article_location = {Oxford},
   article_number = {FEB},
   doi = {http://dx.doi.org/10.1016/j.carbpol.2019.115503},
   keywords = {Selective oxidation; 23-Dialdehydedextrin; 23-Dialdehydecellulose; Sulfamic acid; 23-Dicarboxydextrin; 23-Dicarboxycellulose},
   language = {eng},
   issn = {0144-8617},
   journal = {Carbohydrate Polymers},
   title = {Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides},
   url = {https://www.sciencedirect.com/science/article/pii/S0144861719311713?via%3Dihub},
   volume = {229},
   year = {2020}
}

TY  - JOUR
ID  - 1762520
AU  - Munster, L. - Hanulikova, B. - Machovsky, M. - Latecka, F. - Kuritka, I. - Vicha, J.
PY  - 2020
TI  - Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides
JF  - Carbohydrate Polymers
VL  - 229
IS  - FEB
SP  - 115503
EP  - 115503
PB  - ELSEVIER SCI LTD
SN  - 01448617
KW  - Selective oxidation
KW  - 23-Dialdehydedextrin
KW  - 23-Dialdehydecellulose
KW  - Sulfamic acid
KW  - 23-Dicarboxydextrin
KW  - 23-Dicarboxycellulose
UR  - https://www.sciencedirect.com/science/article/pii/S0144861719311713?via%3Dihub
N2  - Oxidation of polysaccharides to 2,3-dicarboxypolysaccharides is a two-stage process, where selective oxidation by periodate is followed by secondary oxidation by chlorite. Addition of sulfamic acid before the secondary oxidation influences the molecular weight and degree of oxidation of the product. Here, mechanism of sulfamic acid-catalysed chain scission is elucidated for selectively oxidized cellulose and dextrin. Initially, sulfamic acid sulfonates the aldehyde groups of 2,3-dialdehydepolysaccharide. Introduced -SO3H groups are in ideal position to protonate the oxygen atom of 1-4' glycosidic bond and to trigger acidic hydrolysis. This can be used to obtain a direct control over the molecular weight of the product. Observed slightly lower degree of oxidation was ascribed to the ability of sulfamic acid to scavenge the hypochlorite and thus protect the intermolecular hemiacetals from oxidation. Usually undesirable hypochlorite thus seems to be necessary for preparation of selectively oxidized polysaccharides with degree of oxidation above 90%.
ER  -

MUNSTER, L., B. HANULIKOVA, M. MACHOVSKY, F. LATECKA, I. KURITKA a J. VICHA. Mechanism of sulfonation-induced chain scission of selectively oxidized polysaccharides. \textit{Carbohydrate Polymers}. Oxford: ELSEVIER SCI LTD, 2020, roč.~229, FEB, s.~115503-115512. ISSN~0144-8617. Dostupné z: https://dx.doi.org/10.1016/j.carbpol.2019.115503.

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