Chemical Synthesis of β‐(1,4)‐d‐Oligomannurarates with Purported Anti‐Alzheimer Activity

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2024-11-12 DOI:10.1002/ejoc.202401125
Peng Xu, Xiaofei Shao, Biao Yu
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Abstract

Sodium oligomannate, a sophisticated mixture of acidic linear β‐(1,4)‐d‐oligomannurarate ranging from dimers to decamers with an average molecular weight of 670∼880 Da, has gained conditional approval for the treatment of Alzheimer's disease. Herein, we develop an efficient approach to the chemical synthesis of well‐defined β‐(1,4)‐d‐mannurarate di‐, tetra‐, hexa‐ and octasaccharides (1‐4), utilizing N‐phenyl trifluoroacetimidate donors and thioglycoside acceptors for the stereoselective assembly of the desired β‐(1,4)‐d‐mannuronate linkages. This approach features a straightforward protecting group strategy with only two types of protecting groups: tert‐butyldimethylsilyl (TBS) for the 4‐OH at the non‐reducing end and benzyl (Bn) for free hydroxyl and carboxylic acid moieties, thereby ensuring the stereoselective formation of the β‐mannosyl bonds and facilitating sequential transformation into the target β‐(1,4)‐d‐mannurarate oligosaccharides. The scalability of the present synthesis of these oligosaccharides paves the way for in‐depth structure‐activity relationship studies and pharmacological investigations of sodium oligomannates.
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具有所谓抗老年痴呆活性的 β-(1,4)-d-寡甘露糖醛酸盐的化学合成
低聚甘露酸钠是一种复杂的酸性线性β-(1,4)-d-低聚甘露酸混合物,从二聚体到十聚体,平均分子量为670∼880 Da,已获得有条件批准用于治疗阿尔茨海默病。在此,我们开发了一种高效的化学合成方法,利用 N-苯基三氟乙酰亚氨酸供体和硫代糖苷受体,立体选择性地组装所需的β-(1,4)-d-甘露糖二元、四元、六元和八元糖(1-4)。这种方法的特点是采用直接的保护基策略,只有两种类型的保护基:叔丁基二甲基硅烷基(TBS)用于非还原端的 4-OH,苄基(Bn)用于游离的羟基和羧酸分子,从而确保了 β-甘露糖苷键的立体选择性形成,并促进了向目标 β-(1,4)-d-甘露糖苷酸寡糖的顺序转化。目前合成这些低聚糖的可扩展性为低聚甘露酸钠的深入结构-活性关系研究和药理学调查铺平了道路。
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来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
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