3-磷酸甘油酸

3-磷酸甘油酸(英語:3-phosphoglycerate, 3PGglycerate 3-phosphate GP)是生物細胞中常見的分子之一,也是糖解作用卡爾文循環過程裏的中間產物。(註:在卡爾文循環當中簡寫為PGA)

3-磷酸甘油酸
IUPAC名
(2R)-2-Hydroxy-3-phosphonooxypropanoic acid
識別
CAS號 820-11-1  checkY
PubChem 439183
ChemSpider 388326
SMILES
 
  • C([C@H](C(=O)O)O)OP(=O)(O)O
ChEBI 17794
性質
化學式 C3H7O7P
摩爾質量 186.06 g·mol−1
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

在糖解作用中,3-磷酸甘油酸是由1,3-雙磷酸甘油酸磷酸甘油酸激酶(Phosphoglycerate kinase)的催化中產生的。每一分子3-雙磷酸甘油酸會使一分子的ADP轉變成為的ATP,原理是接在1,3-雙磷酸甘油酸上的兩個磷酸根,其中有一個轉移到ADP之上。這個反應需要離子(Mg2+)的幫助。

接下來3-磷酸甘油酸將會在磷酸甘油酸變位酶(Phosphoglycerate)的催化下生成2-磷酸甘油酸,在此反應中,原本接在3-磷酸甘油酸,即己催化,下生成2-磷酸甘油酸的碳上的磷酸根,將會轉移到變位酶上;然後原本在變位酶上的磷酸根,則會接到3-磷酸甘油酸的碳上,反應前後的變位酶整體結構沒有變化。與上一步驟相同,此反應同樣需要Mg2+

糖酵解

在糖酵解途徑中,1,3-二磷酸甘油酸在偶聯反應中去磷酸化形成 3-磷酸甘油酸,通過底物水平磷酸化產生兩個ATP[1] 然後,3-PGA 分子上留下的單個磷酸基團從末端碳移動到中心碳,產生 2-磷酸甘油酸酯。這種磷酸基重定位由磷酸甘油酸變位酶催化,該酶也催化逆反應。 [2]

卡爾文-本森循環

不依賴於光的反應(也稱為卡爾文-本森循環)中,合成了兩個 3-磷酸甘油酸分子。 RuBP是一種 5 碳糖,在rubisco酶的催化下進行碳固定,變成不穩定的 6 碳中間體。 然後,該中間體被裂解成兩個獨立的 3-碳 3-PGA 分子。 [3] 所得 3-PGA 分子之一繼續通過 Calvin-Benson 循環再生為 RuBP,而另一個則通過兩個步驟還原形成一分子甘油醛 3-磷酸(G3P):將 3-PGA磷酸化為1, 3-二磷酸甘油酸通過磷酸甘油酸激酶(與糖酵解中的反應相反)生成,隨後由甘油醛 3-磷酸脫氫酶催化生成 G3P。 [4] [5] [6] G3P 最終反應形成糖,如葡萄糖果糖或更複雜的澱粉[7] :156[4] [5]

氨基酸合成

3-磷酸甘油酯(由 3-磷酸甘油酸形成)也是絲氨酸的前體,絲氨酸反過來又可以通過同型半胱氨酸循環產生半胱氨酸甘氨酸[8] [9] [10]

測量

3-磷酸甘油酸可以使用紙色譜[11]以及柱色譜和其他色譜分離方法來分離和測量。 [12] 它可以使用氣相色譜法液相色譜質譜法進行鑑定,並已針對使用串聯質譜技術的評估進行了優化。 [13] [14] [15]

參考文獻

  1. ^ Rye, Connie; Wise, Robert; Jurukovski, Vladimir; DeSaix, Jean; Choi, Jung; Avissar, Yael. https://openstax.org/books/biology/pages/7-2-glycolysis |chapterurl=缺少標題 (幫助). Glycolysis. OpenStax College. 2016 [2023-08-28]. (原始內容存檔於2014-05-30). Rye, Connie; Wise, Robert; Jurukovski, Vladimir; DeSaix, Jean; Choi, Jung; Avissar, Yael (2016). "Glycolysis"頁面存檔備份,存於互聯網檔案館). Biology頁面存檔備份,存於互聯網檔案館). OpenStax College.
  2. ^ Rose, Z.B.; Dube, S. Rates of phosphorylation and dephosphorylation of phosphoglycerate mutase and bisphosphoglycerate synthase. Journal of Biological Chemistry. 1976, 251 (16): 4817–4822. PMID 8447. doi:10.1016/S0021-9258(17)33188-5 . Rose, Z.B.; Dube, S. (1976). "Rates of phosphorylation and dephosphorylation of phosphoglycerate mutase and bisphosphoglycerate synthase". Journal of Biological Chemistry. 251 (16): 4817–4822. doi:10.1016/S0021-9258(17)33188-5. PMID 8447頁面存檔備份,存於互聯網檔案館).
  3. ^ Andersson, I. Catalysis and regulation in Rubisco. Journal of Experimental Botany. 2008, 59 (7): 1555–1568. PMID 18417482. doi:10.1093/jxb/ern091 . Andersson, I. (2008). "Catalysis and regulation in Rubisco". Journal of Experimental Botany. 59 (7): 1555–1568. doi:10.1093/jxb/ern091. PMID 18417482頁面存檔備份,存於互聯網檔案館).
  4. ^ 4.0 4.1 Moran, L. The Calvin Cycle: Regeneration. Sandwalk. 2007 [11 May 2021]. (原始內容存檔於2022-09-27). Moran, L. (2007). "The Calvin Cycle: Regeneration"頁面存檔備份,存於互聯網檔案館). Sandwalk. Retrieved 11 May 2021.
  5. ^ 5.0 5.1 Pettersson, G.; Ryde-Pettersson, Ulf. A mathematical model of the Calvin photosynthesis cycle. European Journal of Biochemistry. 1988, 175 (3): 661–672. PMID 3137030. doi:10.1111/j.1432-1033.1988.tb14242.x. Pettersson, G.; Ryde-Pettersson, Ulf (1988). "A mathematical model of the Calvin photosynthesis cycle". European Journal of Biochemistry. 175 (3): 661–672. doi:10.1111/j.1432-1033.1988.tb14242.x. PMID 3137030頁面存檔備份,存於互聯網檔案館).
  6. ^ Fridlyand, L.E.; Scheibe, R. Regulation of the Calvin cycle for CO2 fixation as an example for general control mechanisms in metabolic cycles. Biosystems. 1999, 51 (2): 79–93. PMID 10482420. doi:10.1016/S0303-2647(99)00017-9. Fridlyand, L.E.; Scheibe, R. (1999). "Regulation of the Calvin cycle for CO2 fixation as an example for general control mechanisms in metabolic cycles". Biosystems. 51 (2): 79–93. doi:10.1016/S0303-2647(99)00017-9. PMID 10482420頁面存檔備份,存於互聯網檔案館).
  7. ^ Leegood, R.C.; Sharkey, T.D.; von Caemmerer, S. (編). Photosynthesis: Physiology and Metabolism. Advances in Photosynthesis 9. Kluwer Academic Publishers. 2000. ISBN 978-0-7923-6143-5. doi:10.1007/0-306-48137-5. Leegood, R.C.; Sharkey, T.D.; von Caemmerer, S., eds. (2000). Photosynthesis: Physiology and Metabolism. Advances in Photosynthesis. Vol. 9. Kluwer Academic Publishers. doi:10.1007/0-306-48137-5. ISBN 978-0-7923-6143-5.
  8. ^ Igamberdiev, A.U.; Kleczkowski, L.A. The Glycerate and Phosphorylated Pathways of Serine Synthesis in Plants: The Branches of Plant Glycolysis Linking Carbon and Nitrogen Metabolism. Frontiers in Plant Science. 2018, 9 (318): 318. PMC 5861185 . PMID 29593770. doi:10.3389/fpls.2018.00318 . Igamberdiev, A.U.; Kleczkowski, L.A. (2018). "The Glycerate and Phosphorylated Pathways of Serine Synthesis in Plants: The Branches of Plant Glycolysis Linking Carbon and Nitrogen Metabolism"頁面存檔備份,存於互聯網檔案館). Frontiers in Plant Science. 9 (318): 318. doi:10.3389/fpls.2018.00318. PMC 5861185頁面存檔備份,存於互聯網檔案館. PMID 29593770頁面存檔備份,存於互聯網檔案館).
  9. ^ Ichihara, A.; Greenberg, D.M. Pathway of Serine Formation from Carbohydrate in Rat Liver. PNAS. 1955, 41 (9): 605–609. Bibcode:1955PNAS...41..605I. JSTOR 89140. PMC 528146 . PMID 16589713. doi:10.1073/pnas.41.9.605 . Ichihara, A.; Greenberg, D.M. (1955). "Pathway of Serine Formation from Carbohydrate in Rat Liver"頁面存檔備份,存於互聯網檔案館). PNAS. 41 (9): 605–609. Bibcode:1955PNAS...41..605I頁面存檔備份,存於互聯網檔案館). doi:10.1073/pnas.41.9.605. JSTOR 89140頁面存檔備份,存於互聯網檔案館). PMC 528146頁面存檔備份,存於互聯網檔案館. PMID 16589713頁面存檔備份,存於互聯網檔案館).
  10. ^ Hanford, J.; Davies, D.D. Formation of Phosphoserine from 3-Phosphoglycerate in Higher Plants. Nature. 1958, 182 (4634): 532–533. Bibcode:1958Natur.182..532H. S2CID 4192791. doi:10.1038/182532a0. Hanford, J.; Davies, D.D. (1958). "Formation of Phosphoserine from 3-Phosphoglycerate in Higher Plants". Nature. 182 (4634): 532–533. Bibcode:1958Natur.182..532H頁面存檔備份,存於互聯網檔案館). doi:10.1038/182532a0. S2CID 4192791.
  11. ^ Cowgill, R.W.; Pizer, L.I. Purification and Some Properties of Phosphorylglyceric Acid Mutase from Rabbit Skeletal Muscle. Journal of Biological Chemistry. 1956, 223 (2): 885–895. PMID 13385236. doi:10.1016/S0021-9258(18)65087-2 . Cowgill, R.W.; Pizer, L.I. (1956). "Purification and Some Properties of Phosphorylglyceric Acid Mutase from Rabbit Skeletal Muscle". Journal of Biological Chemistry. 223 (2): 885–895. doi:10.1016/S0021-9258(18)65087-2. PMID 13385236頁面存檔備份,存於互聯網檔案館).
  12. ^ Hofer, H.W. Separation of glycolytic metabolites by column chromatography. Analytical Biochemistry. 1974, 61 (1): 54–61. PMID 4278264. doi:10.1016/0003-2697(74)90332-7. Hofer, H.W. (1974). "Separation of glycolytic metabolites by column chromatography". Analytical Biochemistry. 61 (1): 54–61. doi:10.1016/0003-2697(74)90332-7. PMID 4278264頁面存檔備份,存於互聯網檔案館).
  13. ^ 3-Phosphoglyceric acid (HMDB0000807). Human Metabolome Database. The Metabolomics Innovation Centre. [23 May 2021]. (原始內容存檔於2023-07-06). "3-Phosphoglyceric acid (HMDB0000807)"頁面存檔備份,存於互聯網檔案館). Human Metabolome Database. The Metabolomics Innovation Centre. Retrieved 23 May 2021.
  14. ^ Shibayama, J.; Yuzyuk, T.N.; Cox, J.; et al. Metabolic Remodeling in Moderate Synchronous versus Dyssynchronous Pacing-Induced Heart Failure: Integrated Metabolomics and Proteomics Study. PLOS ONE. 2015, 10 (3): e0118974. Bibcode:2015PLoSO..1018974S. PMC 4366225 . PMID 25790351. doi:10.1371/journal.pone.0118974 . Shibayama, J.; Yuzyuk, T.N.; Cox, J.; et al. (2015). "Metabolic Remodeling in Moderate Synchronous versus Dyssynchronous Pacing-Induced Heart Failure: Integrated Metabolomics and Proteomics Study". PLOS ONE. 10 (3): e0118974. Bibcode:2015PLoSO..1018974S頁面存檔備份,存於互聯網檔案館). doi:10.1371/journal.pone.0118974. PMC 4366225. PMID 25790351頁面存檔備份,存於互聯網檔案館).
  15. ^ Xu, J.; Zhai, Y.; Feng, L. An optimized analytical method for cellular targeted quantification of primary metabolites in tricarboxylic acid cycle and glycolysis using gas chromatography-tandem mass spectrometry and its application in three kinds of hepatic cell lines. Journal of Pharmaceutical and Biomedical Analysis. 2019, 171: 171–179. PMID 31005043. S2CID 125170446. doi:10.1016/j.jpba.2019.04.022. Xu, J.; Zhai, Y.; Feng, L. (2019). "An optimized analytical method for cellular targeted quantification of primary metabolites in tricarboxylic acid cycle and glycolysis using gas chromatography-tandem mass spectrometry and its application in three kinds of hepatic cell lines". Journal of Pharmaceutical and Biomedical Analysis. 171: 171–179. doi:10.1016/j.jpba.2019.04.022. PMID 31005043頁面存檔備份,存於互聯網檔案館). S2CID 125170446.