Argunov Dmitry A, Aladysheva Uliana S, Krylov Vadim B, Nifantiev Nikolay E
Laboratory of Glycoconjugate Chemistry, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Laboratory of Synthetic Glycovaccines, N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky Prospect 47, 119991 Moscow, Russian Federation.
Org Lett. 2024 Sep 27;26(38):8090-8094. doi: 10.1021/acs.orglett.4c02984. Epub 2024 Sep 13.
The importance of natural glycoconjugates containing furanoside residues causes a continued demand for the development of efficient methods for the synthesis of corresponding oligosaccharide derivatives to be used as molecular probes in glycobiological studies. Currently, the chemical synthesis of furanose-containing oligosaccharides often represents a significant challenge because of the lack of short, efficient, and reliable methods for the preparation of selectively substituted furanoside blocks. Herein, we report an easy protocol toward galactofuranose-containing molecules based on the unusual equilibrium between pyranoside and furanoside forms observed for a series of substituted galactosides. The method's utility is illustrated by the syntheses of furanoside-containing oligosaccharides related to the antigenic polysaccharides of and O2ac.
含有呋喃糖苷残基的天然糖缀合物的重要性使得人们持续需要开发高效的方法来合成相应的寡糖衍生物，以便在糖生物学研究中用作分子探针。目前，由于缺乏用于制备选择性取代的呋喃糖苷砌块的简短、高效且可靠的方法，含呋喃糖的寡糖的化学合成常常是一项重大挑战。在此，我们报道了一种基于一系列取代半乳糖苷中观察到的吡喃糖苷和呋喃糖苷形式之间异常平衡来制备含半乳呋喃糖分子的简便方法。通过合成与 和O2ac的抗原多糖相关的含呋喃糖苷的寡糖来说明该方法 的实用性。
