Hunt Kaarel Erik, Miller Annette, Jarg Tatsiana, Kriis Kadri, Kanger Tõnis
Department of Chemistry and Biotechnology, Tallinn University of Technology, Akadeemia tee 15, Tallinn 12618, Estonia.
ACS Omega. 2025 May 7;10(19):20047-20053. doi: 10.1021/acsomega.5c02467. eCollection 2025 May 20.
A selective enzymatic acetylation method for the protection of the second and the sixth positions of thio-d-galactopyranoside was found using immobilized Candida antarctica lipase-B (CAL-B). Unfortunately, it was determined that the immobilized enzyme cannot be recycled effectively. The optimized acetylation method was screened with different thioglycosides and with fully unprotected saccharides. New methods for several new partially protected saccharides were found, while the synthesis of some known saccharides, e.g., the third and the sixth position-protected d-glucose or the fourth position-protected l-rhamnose, was improved. Furthermore, an enzymatic acetal formation between the fourth and the sixth positions was discovered. The main limitation for acetylation reactions with CAL-B has been determined to be the substrate solubility.
使用固定化南极假丝酵母脂肪酶B（CAL-B）发现了一种用于保护硫代-d-吡喃半乳糖苷第二位和第六位的选择性酶促乙酰化方法。不幸的是，已确定固定化酶不能有效地循环利用。用不同的硫代糖苷和完全未保护的糖类筛选了优化的乙酰化方法。发现了几种新的部分保护糖类的新方法，同时改进了一些已知糖类的合成，例如第三位和第六位保护的d-葡萄糖或第四位保护的l-鼠李糖。此外，还发现了第四位和第六位之间的酶促缩醛形成。已确定与CAL-B进行乙酰化反应的主要限制是底物溶解度。
