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硫醇催化甘油醛生成乳酸和甘油酸。

Thiol-catalyzed formation of lactate and glycerate from glyceraldehyde.

作者信息

Weber A L

出版信息

J Mol Evol. 1983;19(3-4):237-43. doi: 10.1007/BF02099971.

DOI:10.1007/BF02099971
PMID:6887266
Abstract

The formation of lactate from glyceraldehyde is catalyzed by the thiol, N-acetylcysteine, at ambient temperature in aqueous sodium phosphate (pH 7.0). The rate of lactate formation is more rapid at higher concentrations of sodium phosphate and is essentially the same in the presence and absence of oxygen. The formation of lactate is efficient, but proceeds slowly with an 8.8% yield of lactate after 16 days from 10 mM glyceraldehyde in the presence of 12.5 mM N-acetylcysteine and 500 mM sodium phosphate (pH 7.0). The formation of glycerate from glyceraldehyde, that occurs in the presence of oxygen and to a small extent when oxygen has been removed, is also catalyzed by the thiol, N-acetylcysteine, under the same conditions. The dramatic increase in the rate of glycerate formation that is brought about by the thiol, N-acetylcysteine, is accompanied by an equally dramatic decrease in the rates of production of glycolate and formate. Presumably, the thiol-dependent formation of lactate and glycerate occurs via their respective thioesters. The significance of these reactions to molecular evolution is discussed.

摘要

在磷酸钠水溶液(pH 7.0)中,在环境温度下,甘油醛形成乳酸是由硫醇N - 乙酰半胱氨酸催化的。在较高浓度的磷酸钠存在下,乳酸形成的速率更快,并且在有氧和无氧条件下基本相同。乳酸的形成是有效的,但在12.5 mM N - 乙酰半胱氨酸和500 mM磷酸钠(pH 7.0)存在下,从10 mM甘油醛开始,16天后乳酸的产率为8.8%,反应进行得较慢。在相同条件下,硫醇N - 乙酰半胱氨酸也催化甘油醛在有氧存在时以及在去除氧气后少量情况下形成甘油酸。硫醇N - 乙酰半胱氨酸引起的甘油酸形成速率的显著增加伴随着乙醇酸和甲酸生成速率同样显著的降低。推测,硫醇依赖性的乳酸和甘油酸形成是通过它们各自的硫酯进行的。讨论了这些反应对分子进化的意义。

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1
Thiol-catalyzed formation of lactate and glycerate from glyceraldehyde.硫醇催化甘油醛生成乳酸和甘油酸。
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引用本文的文献

1
Alanine synthesis from glyceraldehyde and ammonium ion in aqueous solution.水溶液中由甘油醛和铵离子合成丙氨酸。
J Mol Evol. 1985;21:351-5. doi: 10.1007/BF02115654.
2
Prebiotic formation of 'energy-rich' thioesters from glyceraldehyde and N-acetylcysteine.由甘油醛和N-乙酰半胱氨酸进行益生元合成“富含能量的”硫酯。
Orig Life Evol Biosph. 1984;15:17-27. doi: 10.1007/BF01809390.
3
Prebiotic sugar synthesis: hexose and hydroxy acid synthesis from glyceraldehyde catalyzed by iron(III) hydroxide oxide.益生元糖的合成:由氢氧化铁(III)催化甘油醛合成己糖和羟基酸。

本文引用的文献

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Long-wavelength ultraviolet photoproduction of amino acids on the primitive Earth.原始地球上长波长紫外线光致氨基酸的生成。
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Formation of the thioester, N,S-diacetylcysteine, from acetaldehyde and N,N'diacetylcystine in aqueous solution with ultraviolet light.在水溶液中,通过紫外线照射,由乙醛和N,N'-二乙酰胱氨酸形成硫酯N,S-二乙酰半胱氨酸。
J Mol Evol. 1981;17(2):103-7. doi: 10.1007/BF01732680.
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Formation of the thioester, N-acetyl, S-lactoylcysteine, by reaction of N-acetylcysteine with pyruvaldehyde in aqueous solution.在水溶液中,N-乙酰半胱氨酸与丙酮醛反应形成硫酯N-乙酰-S-乳酰半胱氨酸。
J Mol Evol. 1982;18(5):354-9. doi: 10.1007/BF01733903.
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Formation of pyrophosphate on hydroxyapatite with thioesters as condensing agents.以硫酯作为缩合剂在羟基磷灰石上形成焦磷酸盐。
Biosystems. 1982;15(3):183-9. doi: 10.1016/0303-2647(82)90002-8.
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Synthesis in sugars in potentially prebiotic conditions.在潜在的益生元条件下糖类的合成。
Nature. 1967 Nov 4;216(5114):455. doi: 10.1038/216455a0.