嗜极细菌细胞膜中的一种关键糖脂--Deinococcucin A 的首次全合成。

IF 2.5 3区化学 Q2 CHEMISTRY, ORGANIC

European Journal of Organic Chemistry Pub Date : 2024-11-06 DOI:10.1002/ejoc.202400879

Jonathan Martins, Abed Bil, José Kovensky, Sylvestre Toumieux, Sylvain Laclef

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引用次数: 0

摘要

Deinococcucin A 是一种从木匠蚁肠道细菌中分离出来的次级代谢物，木匠蚁是嗜极端细菌 Deinoccocus 家族的成员。其结构是一种含有 N-乙酰葡糖胺的糖脂，在 α 异构体位置与手性 2,3-二羟基丙酰胺分子相连。我们成功地采用了一种新策略，直接从 N-乙酰葡糖胺开始，以高效的方式将烯丙基转化为相应的手性 α-羟基酰胺。其中使用了三个关键步骤：使用 TCCA 将伯胺氧化成腈，以及在钯（II）催化条件下将其水解成相应的酰胺。合成只需 10 个步骤即可完成，总产率为 3%。

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First Total Synthesis of Deinococcucin A, a Key Glycolipid Found in Cell Membranes of Extremophilic Bacteria.

Deinococcucin A is a secondary metabolite isolated from a gut bacteria of carpenter ant, member of extremophilic Deinoccocus family. The structure is a glycolipid containing N-acetyl glucosamine, linked in α anomeric position to a chiral 2,3-dihydroxypropanamide moiety. We succeeded a new strategy starting directly from N-acetylglucosamine and transforming in an efficient manner an allyl group to the corresponding chiral α-hydroxyamide. Three key steps were used: the oxidation of primary amine to nitrile using TCCA, as well as its hydrolysis to the corresponding amide using palladium (II) catalyzed conditions. The synthesis was completed in only 10 steps with an overall yield of 3%.

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来源期刊

European Journal of Organic Chemistry 化学-有机化学

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.