酶促化学合成尿苷二磷酸-N-乙酰葡糖胺和尿苷二磷酸-N-乙酰半乳糖胺类似物用于制备非天然糖胺聚糖。
Chemoenzymatic synthesis of uridine diphosphate-GlcNAc and uridine diphosphate-GalNAc analogs for the preparation of unnatural glycosaminoglycans.
机构信息
Department of Chemistry and Chemical Biology, Center for Biotechnology and Interdisciplinary Studies, Rensselaer Polytechnic Institute, Troy, New York 12180, USA.
出版信息
J Org Chem. 2012 Feb 3;77(3):1449-56. doi: 10.1021/jo202322k. Epub 2012 Jan 12.
Abstract
Eight N-acetylglucosamine-1-phosphate and N-acetylgalactosamine-1-phosphate analogs have been synthesized chemically and were tested for their recognition by the GlmU uridyltransferase enzyme. Among these, only substrates that have an amide linkage to the C-2 nitrogen were transferred by GlmU to afford their corresponding uridine diphosphate(UDP)-sugar nucleotides. Resin-immobilized GlmU showed comparable activity to nonimmobilized GlmU and provides a more facile final step in the synthesis of an unnatural UDP-donor. The synthesized unnatural UDP-donors were tested for their activity as substrates for glycosyltransferases in the preparation of unnatural glycosaminoglycans in vitro. A subset of these analogs was useful as donors, increasing the synthetic repertoire for these medically important polysaccharides.
摘要
已通过化学方法合成了 8 种 N-乙酰氨基葡萄糖-1-磷酸和 N-乙酰半乳糖胺-1-磷酸类似物，并对它们与 GlmU 尿苷酰转移酶的识别能力进行了测试。在这些类似物中，只有与 C-2 氮原子形成酰胺键的底物才被 GlmU 转移，从而生成相应的尿苷二磷酸（UDP）-糖核苷酸。固定在树脂上的 GlmU 表现出与非固定 GlmU 相当的活性，并为非天然 UDP-供体的合成提供了更简单的最后一步。所合成的非天然 UDP-供体被用作糖苷转移酶的底物，以在体外制备非天然糖胺聚糖。这些类似物中有一部分可用作供体，增加了这些具有医学重要性的多糖的合成范围。
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