Synthesis of chirally pure 1-deoxy-d-xylulose-5-phosphate : A substrate for IspC assay to determine M. tb inhibitor.

Chemical sciences journal Pub Date : 2013-12-30
Benson J Edagwa, Prabagaran Narayanasamy
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Abstract

1-Deoxy-D-xylulsose-5-phosphate (DXP) is a key intermediate in the non-mevalonate or methyl erythritol phosphate (MEP) pathway for the biosynthesis of isoprenoid, which are essential building blocks involved in the construction of pathogens growth. Since the homologous enzymes of this pathway are not present in vertebrates, including humans, the MEP pathway presents a viable source for antimicrobial drug targets. However, an insight into the features of the enzymes involved in this pathway has been plagued by lack of chirally pure substrates. Here in, we report an efficient synthesis of enantiomerically pure 1-deoxy-D-xylulose-5-phosphate from commercially available 1,2-O-isopropylidene-α-D-xylofuranose through Weinreb amide formation in shorter route.

Abstract Image

Abstract Image

手性纯1-脱氧-d-木醛糖-5-磷酸的合成:用于IspC测定结核分枝杆菌抑制剂的底物。
1-脱氧- d -木糖糖-5-磷酸(DXP)是生物合成类异戊二烯的非甲戊酸或甲基erythritol磷酸(MEP)途径的关键中间体,类异戊二烯是构建病原体生长的重要组成部分。由于该途径的同源酶不存在于包括人类在内的脊椎动物中,因此MEP途径是抗菌药物靶点的可行来源。然而,由于缺乏手性纯底物,对这一途径中涉及的酶的特征的深入研究一直受到困扰。在本文中,我们报道了一种由市售的1,2- o -异丙烯-α- d -木糖呋喃糖通过较短的Weinreb酰胺合成对映体纯度为1-脱氧-d -木酮糖-5-磷酸的高效方法。
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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