Turku Centre for Chemical and Molecular Analytics, Åbo Akademi University, 20500, Turku, Finland.
Laboratory of Molecular Science and Engineering, Åbo Akademi University, 20500, Turku, Finland.
Chemistry. 2023 Aug 1;29(43):e202301489. doi: 10.1002/chem.202301489. Epub 2023 Jun 23.
Acyl group migration has been the subject of several studies. Such migration processes may cause problems during synthesis, isolation, and purification of different acyl-bearing compounds, and have biological relevance, for example, in the metabolism of pharmaceuticals. Considering the recent evidence of acyl group migration being possible even over glycosidic bonds, it could be hypothesized to be involved also in the regulation of biological activity of natural polysaccharides in the host cells. Migrations are mostly observed in carbohydrates, typically having several hydroxyl groups near each other. Several studies have investigated the migration in a single or only a few different carbohydrate molecules, providing different suggestions for the mechanisms of migration, seldom supported by comprehensive computational investigations. In this concept article we discuss the recent progress on the mechanistic aspects of acyl group migration, with carbohydrates in particular focus.
酰基迁移已经成为了多个研究的主题。在不同含酰基化合物的合成、分离和纯化过程中，这种迁移过程可能会引发问题，而且其在药物代谢中也具有生物学意义。鉴于最近有证据表明酰基迁移甚至可能发生在糖苷键上，因此可以假设它也参与了宿主细胞中天然多糖生物活性的调节。这种迁移主要发生在具有几个彼此靠近的羟基的碳水化合物中。有几项研究调查了单个或少数几种不同碳水化合物分子中的迁移，为迁移机制提供了不同的假设，这些假设很少得到全面计算研究的支持。在这篇概念文章中，我们讨论了酰基迁移的机械方面的最新进展，特别是以碳水化合物为重点。
