Abstract
Nucleotide sugars have essential roles in every living creature. They are the building blocks of the biosynthesis of carbohydrates and their conjugates. They are involved in processes that are targets for drug development, and their analogs are potential inhibitors of these processes. Drug development requires efficient methods for the synthesis of oligosaccharides and nucleotide sugar building blocks as well as of modified structures as potential inhibitors. It requires also understanding the details of biological and chemical processes as well as the reactivity and reactions under different conditions. This article addresses all these issues by giving a broad overview on nucleotide sugars in biological and chemical reactions. As the background for the topic, glycosylation reactions in mammalian and bacterial cells are briefly discussed. In the following sections, structures and biosynthetic routes for nucleotide sugars, as well as the mechanisms of action of nucleotide sugar-utilizing enzymes, are discussed. Chemical topics include the reactivity and chemical synthesis methods. Finally, the enzymatic in vitro synthesis of nucleotide sugars and the utilization of enzyme cascades in the synthesis of nucleotide sugars and oligosaccharides are briefly discussed.
Highlights
Nucleotide sugars consist of a monosaccharide and a nucleoside mono- or diphosphate moiety.The term often refers to structures where the nucleotide is attached to the anomeric carbon of the sugar component
uridine diphosphate (UDP)-GlcNAc is a starting point of the synthesis of cytidine monophosphate (CMP)-Neuraminic acid (NeuAc): UDP-GlcNAc is converted in three steps through mannose 6-phosphate to neuraminic acid, which reacts with cytidine triphosphate (CTP) to produce the nucleotide sugar [64]
[112] developed a luminescence-based method to follow the release of UMP and showed that in the reaction catalyzed by PglC, UDP-bacillosamine (UDPEnzymes belonging to the Stealth enzyme family catalyze the transfer of a hexose 1-phosphate to a diBacNAc) releases UMP in the absence of the Pren-P acceptor, which is consistent with the formation sugar acceptor (Scheme 4) [114]
Summary
Nucleotide sugars consist of a monosaccharide and a nucleoside mono- or diphosphate moiety. The term often refers to structures where the nucleotide is attached to the anomeric carbon of the sugar component Such nucleotide sugars are glycosyl and phosphoglycosyl donors in the biosynthesis of carbohydrates and glycoconjugates in all living organisms [1]. Even though the role of such nucleotide sugars may, to certain extent, be similar, the biological reaction pathways are different [2,3]. These “reducing nucleotide sugars” are not discussed in this review. Considering these crucial roles of glycans, efficient methods for the synthesis of oligosaccharides are required. Different worlds do not always meet, and this review attempts to bring together the biology and chemistry of nucleotide sugars by concentrating on the molecules and on the details of their reactions
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