Acyl Group Migration in Pyranosides as Studied by Experimental and Computational Methods

Robert Lassfolk, Manuel Pedrón, Tomás Tejero, Pedro Merino, Johan Wärnå, Reko Leino*

*Tämän työn vastaava kirjoittaja

Tutkimustuotos: LehtiartikkeliArtikkeliTieteellinenvertaisarvioitu

7 Sitaatiot (Scopus)
40 Lataukset (Pure)

Abstrakti

Acyl group migration affects the synthesis, isolation, manipulation and purification of all acylated organic compounds containing free hydroxyl groups, in particular carbohydrates. While several isolated studies on the migration phenomenon in different buffers have been reported, comprehensive insights into the overall migration process in different monosaccharides under similar conditions have been lacking. Here, we have studied the acyl migration in different monosaccharides using five different acyl groups by a combination of experimental, kinetic and theoretical tools. The results show that the anomeric configuration in the monosaccharide has a major influence on the migration rate, together with the relative configurations of the other hydroxyl groups and the nature of the migrating acyl group. Full mechanistic model, based on computations, demonstrates that the acyl migration proceeds through an anionic stepwise mechanism with linear dependence on the [OH] and the pKa of the hydroxyl group toward which the acyl group is migrating.

AlkuperäiskieliEnglanti
Artikkelie202200499
JulkaisuChemistry - A European Journal
Vuosikerta28
Numero34
DOI - pysyväislinkit
TilaJulkaistu - 18 maalisk. 2022
OKM-julkaisutyyppiA1 Julkaistu artikkeli, soviteltu

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