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以（-）-莽草酸为原料立体选择性合成新辛基-β-缬氨烯胺（NOV）和新辛基-4-脱氧-β-缬氨烯胺（NOEV） 。

Novel stereoselective syntheses of -octyl-β-valienamine (NOV) and -octyl-4--β-valienamine (NOEV) from (-)-shikimic acid.

作者信息

Li Feng-Lei, Yu Jiang-Ping, Ding Wei, Sun Mian-Mian, He Yun-Gang, Zhu Xing-Liang, Liu Shi-Ling, Shi Xiao-Xin

机构信息

Engineering Research Center of Pharmaceutical Process Chemistry of the Ministry of Education, East China University of Science and Technology 130 Mei-Long Road Shanghai 200237 P. R. China

Shanghai Qingping Pharmaceutical Co. Ltd. 397 Zhao-Jiang Road, Baihe Town, Qingpu District Shanghai 201710 P. R. China

出版信息

RSC Adv. 2019 Dec 18;9(72):42077-42084. doi: 10.1039/c9ra09235h.

DOI:10.1039/c9ra09235h
PMID:35542836
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9076550/
Abstract

-Octyl-β-valienamine (NOV) 1 and -octyl-4--β-valienamine (NOEV) 2 are potent chemical chaperone drug candidates for the therapy of lysosomal storage disorders. Novel stereoselective syntheses of NOV 1 and NOEV 2 starting from naturally abundant (-)-shikimic acid are described in this article. The common key intermediate compound 5 was first synthesized from readily available (-)-shikimic acid 9 steps in 50% yield. Compound 5 was then converted to NOV 1 5 steps in 61% yield, and it was also converted to NOEV 2 8 steps in 38% yield. In summary, NOV 1 was synthesized 14 steps in 31% overall yield; and NOEV 2 was synthesized 17 steps in 19% overall yield.

摘要

-辛基-β-缬氨酰胺（NOV）1和-辛基-4--β-缬氨酰胺（NOEV）2是用于治疗溶酶体贮积症的强效化学伴侣药物候选物。本文描述了从天然丰富的（-）-莽草酸开始对NOV 1和NOEV 2进行的新型立体选择性合成。常见的关键中间体化合物5首先由易得的（-）-莽草酸经9步反应以50%的产率合成。然后化合物5经5步反应以61%的产率转化为NOV 1，也经8步反应以38%的产率转化为NOEV 2。总之，NOV 1经14步反应以31%的总产率合成；NOEV 2经17步反应以19%的总产率合成。

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本文引用的文献

1
Production and Synthetic Modifications of Shikimic Acid.莽草酸的生产与合成修饰
Chem Rev. 2018 Oct 24;118(20):10458-10550. doi: 10.1021/acs.chemrev.8b00350. Epub 2018 Oct 11.
2
Simultaneous determination of shikimic acid, salicylic acid and jasmonic acid in wild and transgenic Nicotiana langsdorffii plants exposed to abiotic stresses.同时测定暴露于非生物胁迫下的野生型和转基因郎氏烟草植株中莽草酸、水杨酸和茉莉酸的含量。
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Chemical chaperone treatment for galactosialidosis: Effect of NOEV on β-galactosidase activities in fibroblasts.
用于半乳糖唾液酸贮积症的化学伴侣疗法：NOEV对成纤维细胞中β-半乳糖苷酶活性的影响。
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Expanding horizons of shikimic acid. Recent progresses in production and its endless frontiers in application and market trends.拓展莽草酸的视野。生产方面的最新进展及其在应用和市场趋势方面的无尽前沿。
Appl Microbiol Biotechnol. 2013 May;97(10):4277-87. doi: 10.1007/s00253-013-4840-y. Epub 2013 Apr 5.
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Pharmacological chaperones as therapeutics for lysosomal storage diseases.药理学伴侣作为溶酶体贮积病的治疗方法。
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Concise syntheses of potent chaperone drug candidates, N-octyl-4-epi-β-valinenamine (NOEV) and its 6-deoxy derivative, from (+)-proto-quercitol.从（+）-原儿茶醛出发简明合成具有效力的伴侣药物候选物 N-辛基-4-表-β-缬氨醇胺（NOEV）及其 6-脱氧衍生物。
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A short overview on the medicinal chemistry of (-)-shikimic acid.(-)-莽草酸的药物化学简述。
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