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. 2018 Aug 13;23(8):2017.
doi: 10.3390/molecules23082017.

Synthesis and Preliminary Evaluation of Biological Activity of Glycoconjugates Analogues of Acyclic Uridine Derivatives

Roman Komor  1 , Gabriela Pastuch-Gawolek  2   3 , Ewelina Krol  4 , Wieslaw Szeja  5
Affiliations

Synthesis and Preliminary Evaluation of Biological Activity of Glycoconjugates Analogues of Acyclic Uridine Derivatives

Roman Komor et al. Molecules. .

Abstract

Herein we present the methodology for obtaining glycosyltransferase inhibitors, analogues of natural enzyme substrates of donor-type: UDP-glucose and UDP-galactose. The synthesis concerned glycoconjugates, nucleoside analogues containing an acyclic ribose mimetic linked to a uracil moiety in their structure. The biological activity of the synthesised compounds was determined on the basis of their ability to inhibit the model enzyme action of β-1,4-galactosyltransferase from bovine milk. The obtained results allowed to expand and supplement the existing library of synthetic compounds that are able to regulate the biological activity of enzymes from the GT class.

Keywords: acyclic uridine derivatives; glycoconjugates; glycosyltransferase inhibitors; glycosyltransferases; thioglycosides.

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Conflict of interest statement

The authors declare no conflicts of interest.

Figures

Figure 1
Figure 1
(A) Natural GTs substrate; (B) structures of synthesised GTs inhibitors.
Scheme 1
Scheme 1
The general idea of GT inhibitors synthesis.
Scheme 2
Scheme 2
Synthesis of 1-thiosugars and the corresponding 1-thioglycosides.
Scheme 3
Scheme 3
Application of 1,6-anhydrosugars in α-1-thioglyosides synthesis.
Scheme 4
Scheme 4
Synthesis of acyclic uridine derivatives.
Scheme 5
Scheme 5
Synthesis of glycoconjugates of acyclic uridine derivatives.
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