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DL-Glyceraldehyde-3-phosphate

(Synonyms: DL-甘油醛3-磷酸) 目录号 : GC43490

DL-甘油醛-3-磷酸天冬氨酸氨基转移酶阳离子和阴离子同工酶的一种时间依赖性抑制剂。.

DL-Glyceraldehyde-3-phosphate Chemical Structure

Cas No.:591-59-3

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产品描述

DL-Glyceraldehyde 3-phosphate is a time-dependent inhibitor of the cationic and anionic isozymes of aspartate aminotransferase[1]. DL-Glyceraldehyde-3-phosphate, as an intermediate in several metabolic pathways, can be derived from fructose 1,6-bisphosphate by fructose bisphosphate aldolase in a reaction that also produces dihydroxyacetone phosphate (DHAP). It is processed to 1,3-bisphosphoglycerate by glyceraldehyde phosphate dehydrogenase and NAD+[2].

In vitro, DL-glyceraldehyde 3-phosphate has inhibition on the pyridoxamine form of the cationic isozyme with Ki of 0.084 mM. DL-glyceraldehyde 3-phosphate has inhibition on the pyridoxamine form of the anionic isozyme with Ki of 0.39 mM[2]. At a concentration of 2.5 mM, DL-glyceraldehyde 3-phosphate has a bactericidal effect upon Escherichia coli[3].

In vivo, phosphatidylethanolamine and phosphatidylglycerol accumulation are inhibited to the same extent by the addition of DL-glyceraldehyde 3-phosphate to a culture of E. coli[3].

References:
[1]Kopelovich L, et al. Kinetics of the inhibition of aspartate aminotransferase isozymes by DL-glyceraldehyde 3-phosphate. Eur J Biochem. 1971 Jun 11;20(3):351-62.
[2]Song J, et al. The Multiple Roles of Glucose-6-Phosphate Dehydrogenase in Tumorigenesis and Cancer Chemoresistance. Life (Basel). 2022 Feb 12;12(2):271.
[3] Tang CT, et al. L-Glyceraldehude 3-phosphate, a bactericidal agent. Antimicrob Agents Chemother. 1977 Jan;11(1):147-53.

DL-甘油醛-3-磷酸是冬氨酸氨基转移酶阳离子和阴离子同工酶的一种时间依赖性抑制剂[1]。DL-甘油醛-3-磷酸作为多种代谢途径的中间产物,可通过果糖二磷酸醛缩酶从 1,6-二磷酸果糖中提取,在反应中还会产生磷酸二羟丙酮(DHAP)。在磷酸甘油醛脱氢酶和 NAD+ 的作用下,它被加工成 1,3-二磷酸甘油酯[2]。

在体外,DL-甘油醛-3-磷酸对阳离子同工酶的吡多胺形式具有抑制作用,Ki 为 0.084 mM。DL-甘油醛-3-磷酸对阴离子同工酶的吡多胺形式有抑制作用,Ki 为 0.39 mM[2]。2.5 毫摩尔浓度的DL-甘油醛-3-磷酸对大肠杆菌有杀菌作用[3]。

在大肠杆菌培养物中加入 DL-甘油醛-3-磷酸,可在相同程度上抑制磷脂酰乙醇胺和磷脂酰甘油的积累[3]。

Chemical Properties

Cas No. 591-59-3 SDF
别名 DL-甘油醛3-磷酸
化学名 2-hydroxy-3-(phosphonooxy)-propanal
Canonical SMILES OP(OCC(O)C=O)(O)=O
分子式 C3H7O6P 分子量 170.1
溶解度 50 mg/ml in water 储存条件 Store at -20°C
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1 mM 5.8789 mL 29.3945 mL 58.7889 mL
5 mM 1.1758 mL 5.8789 mL 11.7578 mL
10 mM 0.5879 mL 2.9394 mL 5.8789 mL
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Research Update

In vitro effect of n-hexane and its metabolites on selected enzymes in glycolysis, pentose phosphate pathway and citric acid cycle

Brain Res 1984 Apr 9;297(1):145-50.PMID:6232975DOI:10.1016/0006-8993(84)90551-1.

The effect of n-hexane, 2-hexanol, 5-hydroxy-2-hexanone, 2,5-hexanediol, methyl n-butyl ketone ( MnBK ) and 2,5-hexanedione (2,5-HD) has been studied in vitro on crystalline glyceraldehyde-3-phosphate dehydrogenase (GAPDH), DL-Glyceraldehyde-3-phosphate: NAD oxidoreductase (phosphorylating) EC. 1.2.1.12 and phosphofructokinase (PFK) ATP: D-fructose-6-phosphate-1-phosphotransferase; EC. 2.7.1.11 and lactic dehydrogenase (LDH) L-lactate: NAD+ oxidoreductase, EC. 1.1.1.27. MnBK and 2,5-HD both inhibited GAPDH and PFK activities selectively. n-Hexane and 2-hexanol had no effect on GAPDH and PFK activities; 5-hydroxy-2-hexanone and 2,5-hexanediol exhibited a slight inhibitory effect on these enzymes. Neither metabolites of n-hexane have any effect on LDH activity. 2,5-Hexanedione did not inhibit transketolase (D-sedoheptulose-7-phosphate: D-glyceraldehyde-3-phosphate glycolaldehyde transferase, EC. 2.2.1.1) and succinate dehydrogenase (succinate: 2,6-dichlorophenol-indophenol oxidoreductase, EC. 1.3.99.1) activities. The levels of ATP were reduced in 2,5-HD-treated cat sciatic nerves and returned to normal levels by exposing the nerve to sodium pyruvate.