PhD Scientific Days 2020

Pharmaceutical Sciences I. Lectures

Photoinitiated Thiol-Ene Additions on Various Unsaturated Carbohydrates with Carbohydrate Thiols

Előadó neve

Dr. Kelemen, Viktor

Előadó munkahelye

University of Debrecen, Department of Pharmaceutical Chemistry

Előadó telefonszáma

0630 221 4086

Előadó e-mail címe

kelemen.viktor@pharm.unideb.hu

Az előadás címe

Photoinitiated Thiol-Ene Additions on Various Unsaturated Carbohydrates with Carbohydrate Thiols

Szerző(k) neve és munkahelye

Kelemen, Viktor 1, 2 ; Bege, Miklós 1, 2; Eszenyi, Dániel 1; Debreczeni, Nóra 1, 3; Herczegh, Pál 1; Borbás, Anikó 1

1 University of Debrecen, Department of Pharmaceutical Chemistry,. 4032 Debrecen, Egyetem tér 1.
2 University of Debrecen, Doctoral School of Pharmaceutical Sciences, 4032 Debrecen, Nagyerdei körút 98.
3 University of Debrecen, Doctoral School of Chemistry, 4032 Debrecen, Egyetem tér 1.

Szekció

Pharmaceutical Sciences I. Lectures

Language of the presentation

English

Section, first choice

Pharmaceutical Sciences

Section, second choice

Molecular Sciences

Összefoglaló szövege

Introduction
Carbohydrates bearing α-glycosidic bonds are abundant in the nature, from the tiny procaryotes to the developed organisms. The O-glycosidic bond is, however, inherently susceptible to enzymatic degradation, so we focused our attention on synthesizing the S-glycosidic analogues of biologically relevant carbohydrates. Thioglycosides are more stable in biological environments, therefore they are better suited for glycobiological and drug development studies than the natural O-glycosides. However, forming the critically important 1,2-cis-α-thioglycosidic bond is an extremely difficult task, there is no known method that can be applied generally.

Methods
Photoinitiated thiol-ene addition reaction was applied to form tiodisaccharide mimetics with outstanding regio- and stereoselectivity via reacting exoglycals and carbohydrate thiols [1]. This method was also used on 2-substituted glycals, and we found that it is an outstanding method for the formation of the challenging 1,2-cis-α-glycosidic bond [2]. An unusual phenomenon has also been observed: cooling promotes while heating hinders the completion of the addition reaction [3].

Results and conclusion
In this study, the synthesis of numerous biologically relevant and potentially antibiotic thioglycosides is described in detail. The reaction was extended to numerous thiols and unsaturated carbohydrates while the effects of the various conditions (temperature, solvent, initiation time) on the conversion and isolated yield were also examined thoroughly.

[1] M. Fiore, A. Marra, A. Dondoni, J. Org. Chem., 2009, 74 (11), 4422–442
[2] L. Lázár, M. Csávás, M. Herczeg, P. Herczegh, A. Borbás, Org. Lett. 2012, 14, 4650– 4653
[3] D. Eszenyi, V. Kelemen, F. Balogh, M. Bege, M. Csávás, P. Herczegh, A. Borbás, Chem. Eur. J. 2018, 24, 4532-4536.


This research was funded by Gedeon Richter’s Talentum Foundation (1103 Budapest, Gyömrői út 19-21.), the “Debrecen Venture Catapult Program” (EFOP-3.6.1-16-2016-00022 and EFOP-3.6.3-VEKOP-16-2017-00009), and the ÚNKP-19-3 New National Excellence Program of the Ministry for Innovation and Technology. The research was also supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008.

Additional Information

Supervisor: Anikó Borbás
e-mail address: borbas.aniko@pharm.unideb.hu
This research was funded by Gedeon Richter’s Talentum Foundation (1103 Budapest, Gyömrői út 19-21.), the “Debrecen Venture Catapult Program” (EFOP-3.6.1-16-2016-00022, and EFOP-3.6.3-VEKOP-16-2017-00009), and the ÚNKP-19-3 New National Excellence Program of the Ministry for Innovation and Technology. The research was also supported by the EU and co-financed by the European Regional Development Fund under the project GINOP-2.3.2-15-2016-00008.

Bemutatás módja

Szóbeli

Kind

Szabad

Status

elfogadva

Accepted presentation method

szóbeli

Előadás fájl jóváhagyás

nem rendelkezett róla

Előadó

4699

Start

10:55

End

11:10

Authors (legacy)

Kelemen, Viktor 1, 2 ; Bege, Miklós 1, 2; Eszenyi, Dániel 1; Debreczeni, Nóra 1, 3; Herczegh, Pál 1; Borbás, Anikó 1

1 University of Debrecen, Department of Pharmaceutical Chemistry,. 4032 Debrecen, Egyetem tér 1.
2 University of Debrecen, Doctoral School of Pharmaceutical Sciences, 4032 Debrecen, Nagyerdei körút 98.
3 University of Debrecen, Doctoral School of Chemistry, 4032 Debrecen, Egyetem tér 1.