Dual effect of benzyl alcohol on alpha-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity

Pavlović, Marija; Dimitrijević, Aleksandra; Bezbradica, Dejan; Milosavić, Nenad; Gavrović-Jankulović, Marija; Šegan, Dejan M.; Veličković, Dušan

doi:10.1016/j.carres.2013.08.028

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2014

Authors

Pavlović, Marija
Dimitrijević, Aleksandra
Bezbradica, Dejan

Milosavić, Nenad
Gavrović-Jankulović, Marija

Šegan, Dejan M.

Veličković, Dušan

Article (Published version)

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Abstract

Benzyl alcohol, a potent anesthetic and bacteriostatic, can be efficiently glucosylated by alpha-glucosidase from Saccharomyces cerevisiae to produce benzyl alcohol alpha-glucoside with a 75% yield. However, while studying the transglucosylation reaction conditions, it was found out that benzyl alcohol is a non-competitive inhibitor of alpha-glucosidase's hydrolytic activity (K-i = 18 mM, toward maltose). Due to its interesting ability to be glycosylated by the enzyme and to inhibit its hydrolytic activity, we proposed a plausible mechanism for the phenolic alpha-glucosydase inhibitor's binding, since the mechanism of inhibition has not yet been elucidated.

Keywords:

Benzyl alcohol / alpha-Glucosidase inhibition / Transglucosylation / Primary hydrolysis

Source:
Carbohydrate Research, 2014, 387, 14-18

Publisher:

Elsevier Sci Ltd, Oxford

Funding / projects:

DOI: 10.1016/j.carres.2013.08.028

ISSN: 0008-6215

PubMed: 24531390

WoS: 000332959100004

Scopus: 2-s2.0-84894090228

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	7
	6

TY  - JOUR
AU  - Pavlović, Marija
AU  - Dimitrijević, Aleksandra
AU  - Bezbradica, Dejan
AU  - Milosavić, Nenad
AU  - Gavrović-Jankulović, Marija
AU  - Šegan, Dejan M.
AU  - Veličković, Dušan
PY  - 2014
UR  - http://TechnoRep.tmf.bg.ac.rs/handle/123456789/2753
AB  - Benzyl alcohol, a potent anesthetic and bacteriostatic, can be efficiently glucosylated by alpha-glucosidase from Saccharomyces cerevisiae to produce benzyl alcohol alpha-glucoside with a 75% yield. However, while studying the transglucosylation reaction conditions, it was found out that benzyl alcohol is a non-competitive inhibitor of alpha-glucosidase's hydrolytic activity (K-i = 18 mM, toward maltose). Due to its interesting ability to be glycosylated by the enzyme and to inhibit its hydrolytic activity, we proposed a plausible mechanism for the phenolic alpha-glucosydase inhibitor's binding, since the mechanism of inhibition has not yet been elucidated.
PB  - Elsevier Sci Ltd, Oxford
T2  - Carbohydrate Research
T1  - Dual effect of benzyl alcohol on alpha-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity
EP  - 18
SP  - 14
VL  - 387
DO  - 10.1016/j.carres.2013.08.028
ER  -

@article{
author = "Pavlović, Marija and Dimitrijević, Aleksandra and Bezbradica, Dejan and Milosavić, Nenad and Gavrović-Jankulović, Marija and Šegan, Dejan M. and Veličković, Dušan",
year = "2014",
abstract = "Benzyl alcohol, a potent anesthetic and bacteriostatic, can be efficiently glucosylated by alpha-glucosidase from Saccharomyces cerevisiae to produce benzyl alcohol alpha-glucoside with a 75% yield. However, while studying the transglucosylation reaction conditions, it was found out that benzyl alcohol is a non-competitive inhibitor of alpha-glucosidase's hydrolytic activity (K-i = 18 mM, toward maltose). Due to its interesting ability to be glycosylated by the enzyme and to inhibit its hydrolytic activity, we proposed a plausible mechanism for the phenolic alpha-glucosydase inhibitor's binding, since the mechanism of inhibition has not yet been elucidated.",
publisher = "Elsevier Sci Ltd, Oxford",
journal = "Carbohydrate Research",
title = "Dual effect of benzyl alcohol on alpha-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity",
pages = "18-14",
volume = "387",
doi = "10.1016/j.carres.2013.08.028"
}

Pavlović, M., Dimitrijević, A., Bezbradica, D., Milosavić, N., Gavrović-Jankulović, M., Šegan, D. M.,& Veličković, D.. (2014). Dual effect of benzyl alcohol on alpha-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity. in Carbohydrate Research
Elsevier Sci Ltd, Oxford., 387, 14-18.
https://doi.org/10.1016/j.carres.2013.08.028

Pavlović M, Dimitrijević A, Bezbradica D, Milosavić N, Gavrović-Jankulović M, Šegan DM, Veličković D. Dual effect of benzyl alcohol on alpha-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity. in Carbohydrate Research. 2014;387:14-18.
doi:10.1016/j.carres.2013.08.028 .

Pavlović, Marija, Dimitrijević, Aleksandra, Bezbradica, Dejan, Milosavić, Nenad, Gavrović-Jankulović, Marija, Šegan, Dejan M., Veličković, Dušan, "Dual effect of benzyl alcohol on alpha-glucosidase activity: efficient substrate for high yield transglucosylation and non-competitive inhibitor of its hydrolytic activity" in Carbohydrate Research, 387 (2014):14-18,
https://doi.org/10.1016/j.carres.2013.08.028 . .