单磷酰脂A模拟物RC-529的高效合成

IF 1.2 4区化学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY

Journal of Carbohydrate Chemistry Pub Date : 2021-01-01 DOI:10.1080/07328303.2021.2016793

Chengkai Zhou , Zhuojia Xu , Gen Li , Qi Gao , Qiang Sui , Tiehai Li

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引用次数: 0

摘要

本文描述了一种高效的、易于合成强效疫苗佐剂RC-529的方法。该合成策略依赖于正交保护基团的灵活使用，从而可以分别实现选择性磷酸化、糖基化和酰化。此外，使用易裂解的2-萘甲基(Nap)醚和烯丙基酯作为永久保护基团，极大地促进了最终的全局去保护步骤，以获得纯RC-529。本研究对脂质A及其衍生物的合成具有重要意义。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Efficient synthesis of monophosphoryl lipid A mimetic RC-529

An efficient approach for the facile synthesis of a potent vaccine adjuvant RC-529 is described. The synthetic strategy relies on the flexible use of orthogonal protecting groups, which makes it possible to accomplish selective phosphorylation, glycosylation and acylation, respectively. In addition, the use of readily cleaved 2-naphthylmethyl (Nap) ether and allyl esters as permanent protecting groups greatly facilitates the final global deprotection steps to obtain pure RC-529. This work will contribute to the synthesis of lipid A and its derivatives.

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来源期刊

Journal of Carbohydrate Chemistry 化学-生化与分子生物学

CiteScore

2.10

自引率

0.00%

发文量

审稿时长

1 months

期刊介绍： The Journal of Carbohydrate Chemistry serves as an international forum for research advances involving the chemistry and biology of carbohydrates. The following aspects are considered to fall within the scope of this journal: -novel synthetic methods involving carbohydrates, oligosaccharides, and glycoconjugates- the use of chemical methods to address aspects of glycobiology- spectroscopic and crystallographic structure studies of carbohydrates- computational and molecular modeling studies- physicochemical studies involving carbohydrates and the chemistry and biochemistry of carbohydrate polymers.