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Achiral Hydroxypyruvaldehyde Phosphate as a Platform for Multi-Aldolases Cascade Synthesis of Diuloses and for a Quadruple Acetaldehyde Addition Catalyzed by 2-Deoxyribose-5-Phosphate Aldolases
ACS Catalysis ( IF 11.3 ) Pub Date : 2019-09-23 , DOI: 10.1021/acscatal.9b02668
Victor Laurent 1 , Virgil Hélaine 1 , Carine Vergne-Vaxelaire 2 , Lionel Nauton 1 , Mounir Traikia 1 , Jean-Louis Petit 2 , Marcel Salanoubat 2 , Véronique de Berardinis 2 , Marielle Lemaire 1 , Christine Guérard-Hélaine 1
Affiliation  

The 1,4-dicarbonyl unit is found in numerous molecules of biological interest, many of which are also polyhydroxylated. We developed a general, one-pot, multistep, stereoselective enzymatic method to prepare diuloses of structural diversity from achiral hydroxypyruvaldehyde phosphate (HPP) as the common electrophile for various aldolases. Surprisingly, for 2-deoxyribose-5-phosphate aldolases, HPP was an acceptor of choice for the multiple addition of acetaldehyde, widening the scope of longer-chain aldol adducts.

中文翻译:

非手性羟基丙酮醛磷酸酯作为多醛糖酶级联合成的平台和2-脱氧核糖5-磷酸醛缩酶催化四乙醛加成反应的平台。

在许多具有生物学意义的分子中发现了1,4-二羰基单元,其中许多分子也被多羟基化。我们开发了一种通用的,一锅多步的立体选择性酶法,以从非手性羟基丙酮醛磷酸酯(HPP)作为各种醛缩酶的常用亲电子试剂来制备结构多样性的diulose。出乎意料的是,对于2-脱氧核糖-5-磷酸醛缩酶,HPP是乙醛多次添加的选择受体,从而扩大了长链醛缩醛加合物的范围。
更新日期:2019-09-23
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