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| Content Provider | MDPI |
|---|---|
| Author | Bayer, Nils Schubert, Uwe Sentürk, Zehra Rudloff, Silvia Frank, Sandra Hausmann, Heike Geyer, Hildegard Geyer, Rudolf Preissner, Klaus Galuska, Sebastian |
| Abstract | N-acetylneuraminic acid (Neu5Ac) represents the most common terminal carbohydrate residue in many mammalian glycoconjugates and is directly involved in a number of different physiological as well as pathological cellular processes. Endogenous sialic acids derive from the biosynthetic precursor molecule N-acetyl-D-mannosamine (ManNAc). Interestingly, N-acyl-analogues of D-mannosamine (ManN) can also be incorporated and converted into corresponding artificial sialic acids by eukaryotic cells. Within this study, we optimized a protocol for the chemical synthesis of various peracetylated ManN derivatives resulting in yields of approximately 100%. Correct molecular structures of the obtained products ManNAc, N-propanoyl-ManN (ManNProp) and N-butyl-ManN (ManNBut) were verified by GC-, ESI-MS- and NMR-analyses. By applying these substances to human umbilical vein endothelial cells (HUVECs), we could show that each derivative was metabolized to the corresponding N-acylneuraminic acid variant and subsequently incorporated into nascent glycoproteins. To investigate whether natural and/or artificial sialic acid precursors are able to modulate the angiogenic capacity of HUVECs, a spheroid assay was performed. By this means, an increase in total capillary length has been observed when cells incorporated N-butylneuraminic acid (Neu5But) into their glycoconjugates. In contrast, the natural precursor ManNAc inhibited the growth of capillaries. Thus, sialic acid precursors may represent useful agents to modulate blood vessel formation. |
| File Size | 558080 |
| Ending Page | 2586 |
| Page Count | 16 |
| Starting Page | 2571 |
| File Format | |
| e-ISSN | 14203049 |
| DOI | 10.3390/molecules18032571 |
| Journal | Molecules |
| Issue Number | 3 |
| Volume Number | 18 |
| Language | English |
| Publisher Date | 2013-02-26 |
| Access Restriction | Open |
| Subject Keyword | glycoengineering artificial sialic acids mannosamine angiogenesis |
| Content Type | Text |
| Resource Type | Article |
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