Chemical and enzymatic methodologies for the synthesis of enantiomerically pure glyceraldehyde 3-phosphates
Chemical and enzymatic methodologies for the synthesis of enantiomerically pure glyceraldehyde 3-phosphates
复制标题
DOI：
10.1016/j.carres.2013.12.023
复制
发表时间：
2014-05-07
影响因子：
3.1
通讯作者：
Wohlgemuth, Roland
中科院分区：
文献类型：
--
作者：
Gauss, Dominik;Schoenenberger, Bernhard;Wohlgemuth, Roland
甘油醛3-磷酸是许多生物体内许多中心代谢途径的重要中间体。D-甘油醛-3-磷酸(D-GAP)是糖酵解过程中的关键中间体，也存在于多种代谢途径中。相反的对映体L-甘油醛-3-磷酸(L-GAP)已经在一些令人兴奋的新途径中被发现。本文报道了3-磷酸甘油醛对映体的改进合成方法。D-GAP是通过D-果糖-6-磷酸的高碘酸盐裂解合成的，而L-GAP是通过酶促L-甘油醛磷酸化得到的。H-1-和P-31核磁共振波谱用于检测GAP随时间的pH依赖行为，并识别潜在的降解产物。结果表明，GAP在pH为4以下的酸性水溶液中很稳定，在pH为7时生成甲基乙二醛，而在碱性条件下生成乳酸。(C)2014爱思唯尔有限公司。保留所有权利。
Glyceraldehyde 3-phosphates are important intermediates of many central metabolic pathways in a large number of living organisms. D-Glyceraldehyde 3-phosphate (D-GAP) is a key intermediate during glycolysis and can as well be found in a variety of other metabolic pathways. The opposite enantiomer, L-glyceraldehyde 3-phosphate (L-GAP), has been found in a few exciting new pathways. Here, improved syntheses of enantiomerically pure glyceraldehyde 3-phosphates are reported. While D-GAP was synthesized by periodate cleavage of D-fructose 6-phosphate, L-GAP was obtained by enzymatic phosphorylation of L-glyceraldehyde. H-1- and P-31 NMR spectroscopy was applied in order to examine pH-dependent behavior of GAP over time and to identify potential degradation products. It was found that GAP is stable in acidic aqueous solution below pH 4. At pH 7, methylglyoxal is formed, whereas under alkaline conditions, the formation of lactic acid could be observed. (C) 2014 Elsevier Ltd. All rights reserved.