Aldolase as a Chirality Intersection of L-Amino Acids and D-Sugars

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• 作者：Toratane Munegumi
• 关键词：Aldolase ; Metabolism ; L ; amino acid ; D ; sugar ; Chirality
• 刊名：Origins of Life and Evolution of Biospheres
• 出版年：2015
• 出版时间：June 2015
• 年：2015
• 卷：45
• 期：1-2
• 页码：173-182
• 全文大小：1,264 KB
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• 作者单位：Toratane Munegumi (1)
  
  1. Naruto University of Education, Naruto, Tokushima, 772-8502, Japan
  
• 刊物主题：Life Sciences, general; Astrophysics and Astroparticles; Earth Sciences, general; Astronomy, Observations and Techniques; Biochemistry, general;
• 出版者：Springer Netherlands
• ISSN：1573-0875

文摘

Aldolase plays an important role in glycolysis and gluconeogenesis to produce D-fructose-1,6-bisphosphate (D-FBP) from dihydroxyacetone phosphate (DHP) and D-glyceraldehyde-3-phosphate (D-GAP). This reaction is stereoselective and retains the D-GAP 2R configuration and yields D-FBP (with the configuration: 3S, 4S, 5R). The 3- and 4-position carbons are the newly formed chiral carbons because the 5-position carbon of D-FBP comes from the 2-position of D-GAP. Although four diastereomeric products, (3S, 4R, 5R), (3R, 4R, 5R), (3R, 4S, 5R), (3S, 4S, 5R), are expected in the nonenzymatic reaction, only the (3S, 4S, 5R) diastereomer (D-FBP) is obtained. Therefore, the chirality in the 3- and 4-positions is induced by the chirality of the enzyme composed of L-amino acid residues. D-Glucose-6-phosphate (D-G6P), which is generated from D-FBP in the gluconeogenesis pathway, produces D-ribose-5-phosphate (D-R5P) in the pentose phosphate pathway. D-R5P is converted to PRPP (5-phosphoribosyl-伪-pyrophosphate), which is used for the de novo synthesis of nucleotides. Ribonucleic acid (RNA) uses the nucleotides as building blocks. The configurations of the 4R-carbon and of the 3S-carbon are retained. The stereochemical structure of RNA is based on 3S as well as 4R (D). The consideration above suggests that aldolase is a key enzyme that determines the 3S configuration in D-R5P. It is thus a chirality intersection between amino acids and sugars, because the sugar chirality is determined by the chiral environment of an L-amino acid protein, aldolase, to produce D-FBP.