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一种有机锗化合物通过烯二醇络合物的形成提高了醛糖碱性异构化为酮糖的初始反应速率。

An Organogermanium Compound Enhances the Initial Reaction Rate of Alkaline Isomerization of an Aldose into a Ketose through Enediol Complex Formation.

作者信息

Sato Katsuyuki, Nagasawa Takae, Kasumi Takafumi

机构信息

1 Asai Germanium Research Institute Co., Ltd.

2 Enzymology and Molecular Biology Laboratory, Department of Chemistry and Life Science, Nihon University.

出版信息

J Appl Glycosci (1999). 2022 Feb 18;69(1):9-13. doi: 10.5458/jag.jag.JAG-2021_0011. eCollection 2022.

DOI:10.5458/jag.jag.JAG-2021_0011
PMID:35493701
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8960003/
Abstract

We previously demonstrated that the organogermanium compound 3-(trihydroxygermyl)propanoic acid (THGP) enhances the enzymatic and alkaline isomerization of an aldose to a ketose through -diol complex formation by multiple mechanisms. Its higher affinity for the ketose than the aldose protects the ketose complex from alkaline decomposition. Furthermore, it has been reported that the aldose-ketose alkaline isomerization pathway includes 1,2-enediol. Therefore, we speculated that the complex-forming ability of THGP could also be applied to enediol, a transient intermediate of alkaline isomerization. To test this prediction, we analyzed the initial rates of glucose or lactose isomerization in a region where there was no substantial difference in pH with and without THGP addition. The results showed that THGP enhanced the rate of fructose or lactulose formation per unit time by approximately 2-fold compared to the control. This finding indicated that THGP could form a complex with the transition state of aldose-ketose alkaline isomerization.

摘要

我们之前证明,有机锗化合物3-(三羟基锗基)丙酸(THGP)通过多种机制形成二醇配合物,增强了醛糖向酮糖的酶促异构化和碱异构化。它对酮糖的亲和力高于醛糖,可保护酮糖配合物不被碱分解。此外,据报道醛糖-酮糖碱异构化途径包括1,2-烯二醇。因此,我们推测THGP的配合物形成能力也可应用于碱异构化的瞬时中间体烯二醇。为了验证这一预测,我们在添加和不添加THGP的情况下,在pH值没有显著差异的区域分析了葡萄糖或乳糖异构化的初始速率。结果表明,与对照组相比,THGP使单位时间内果糖或乳果糖的形成速率提高了约2倍。这一发现表明,THGP可以与醛糖-酮糖碱异构化的过渡态形成配合物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/94804ac28476/JAG-61-009-g04.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/f67cbf60862c/JAG-61-009-g01.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/ed56a833338d/JAG-61-009-g02.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/05fbee49e84e/JAG-61-009-g03.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/94804ac28476/JAG-61-009-g04.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/f67cbf60862c/JAG-61-009-g01.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/ed56a833338d/JAG-61-009-g02.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/05fbee49e84e/JAG-61-009-g03.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/3b69/8960003/94804ac28476/JAG-61-009-g04.jpg

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本文引用的文献

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Efficient Continuous Production of Lactulose Syrup by Alkaline Isomerization Using an Organogermanium Compound.使用有机锗化合物通过碱性异构化高效连续生产乳果糖糖浆
J Appl Glycosci (1999). 2019 Nov 20;66(4):121-129. doi: 10.5458/jag.jag.JAG-2019_0012. eCollection 2019.
2
Efficient Alkaline Isomerization of Lactose to Lactulose in the Presence of an Organogermanium Compound.在有机锗化合物存在下乳糖向乳果糖的高效碱异构化反应
J Appl Glycosci (1999). 2017 May 20;64(2):27-32. doi: 10.5458/jag.jag.JAG-2016_018. eCollection 2017.
3
Efficient Conversion of D-Glucose to D-Fructose in the Presence of Organogermanium Compounds.
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J Appl Glycosci (1999). 2016 May 20;63(2):39-45. doi: 10.5458/jag.jag.JAG-2015_025. eCollection 2016.
4
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5
Organogermanium compound, Ge-132, forms complexes with adrenaline, ATP and other physiological cis-diol compounds.有机锗化合物Ge-132与肾上腺素、三磷酸腺苷及其他生理顺式二醇化合物形成络合物。
Future Med Chem. 2015;7(10):1233-46. doi: 10.4155/fmc.15.62.
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Mechanistic imperatives for aldose-ketose isomerization in water: specific, general base- and metal ion-catalyzed isomerization of glyceraldehyde with proton and hydride transfer.水中醛糖-酮糖异构化的机理要求:甘油醛通过质子和氢化物转移进行的特异性、一般碱催化和金属离子催化的异构化。
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