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吲哚丙酮酸的酮-烯醇互变异构化的NMR研究 被引量:6

An NMR Study on Keto-Enol Tautomerism of Indole-3-Pyruvic Acid
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摘要 吲哚丙酮酸是色氨酸代谢途径中的一种重要α-酮酸,但其酮-烯醇互变异构化现象及互变异构体的NMR数据尚未见报道.该文采用多维NMR技术研究了吲哚丙酮酸在不同溶剂中主要存在形式.使用2D NMR谱对吲哚丙酮酸的烯醇式和酮式结构进行了NMR研究.结果表明吲哚丙酮酸在乙腈溶液中主要以烯醇式结构存在,而在水溶液中主要以酮式结构存在. Indole-3-pyruvic acid is an important a-keto acid in the tryptophan pathway. In this work, two main forms of indole-3-pyruvic acid in acetonitrile and water solutions were studied using multi-dimensional NMR techniques. The results showed that both forms were present, and the enol-form of indole-3-pyruvic acid was the dominant form in acetontrile whereas the keto-form was the main form in water. This work provided detailed assignments for the 1H and 13C NMR signals from both the enol- and keto-forms of indole-3-pyruvic acid, offering essential spectroscopic information for this metabolite.
出处 《波谱学杂志》 CAS CSCD 北大核心 2014年第1期81-90,共10页 Chinese Journal of Magnetic Resonance
基金 国家自然科学基金资助项目(21175149 21221064) 国家重点基础研究发展计划资助项目(2010CB912501)
关键词 液体磁共振(NMR) 归属 2D NMR 吲哚丙酮酸 NMR, assignment, 2D NMR, indole-3-pyruvic acid
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参考文献19

  • 1Badenochjones J,Summons R E,Rolfe B G,et al.Phytohormones,Rhizobium mutants,and nodulation in legumes.4.auxin metabolites in pea root-nodules[J].J Plant Growth Regul,1984,3(1):23 39.
  • 2Cooney T P,Nonhebel H M.The measurement and mass-spectral identification of indole-3-pyruvate from tomato shoots[J].Biochem Biophys Res Commun,1989,162(2):761-766.
  • 3Cooney T P,Nonhebel H M.Biosynthesis of indole-3-acetic acid in tomato shoots:measurement,mass-spectral identification and incorporation of-2H from-2H2O into indole-3-acetic acid,D-and L-tryptophan,indole-3-pyruvate and tryptamine[J].Planta,1991,184(3):368-376.
  • 4Moore T C,Shaner C A.Synthesis of indoleacetic acid from tryptophan via indolepyruvic acid in cell-free extracts of pea seedlings[J].Arch Biochem Biophys,1968,127(1):613 621.
  • 5Koga J.Structure and function of indolepyruvate decarboxylase,a key enzyme in indole-3-acetic-acid biosynthesis[J].Biochim Biophys Acta-Protein Struct Molec Enzym,1995,1 249(1):1-13.
  • 6Politi V,Dalessio S,DiStazio G,et al.Recent Advances in Tryptophan Research:Tryptophan and Serotonin Pathways[M].New York:Plenum Press Div Plenum Publishing Corp,1996.
  • 7Perkins M N,Stone T W.Actions of kynurenic acid and quinolinic acid in the rat hippocampus in vivo[J].Exp Neurol,1985,88(3):570-579.
  • 8Libbert E,Brunn K,Drawert A,et al.Pathways of IAA production from tryptophan by plants and by their epiphytic bacteria:metabolism of indolepyruvic acid and indolelactic acid[J].Biol Plant,1970,12(4):246-255.
  • 9Bartolini B,Comiello C,Sella A,et al.Developments in Tryptophan and Serotonin Metabolism[M].New York:Kluwer Academic/Plenum Publ,2003.
  • 10Penrose L,Quastel J H.Metabolic studies in phenylketonuria[J].Biochem J,1937,31(2):266-274.

二级参考文献35

  • 1于贤勇,陈忠.有机双过氧钒化合物的合成及其与小分子相互作用研究[J].波谱学杂志,2007,24(3):365-367. 被引量:2
  • 2Thorburn G D. The placenta, prostaglandins and parturition: a review[J]. Reprod Fert Dev, 1991, 3(3): 277-294.
  • 3Sugimoto Y, Narumiya S, Ichikawa A. Distribution and function of prostanoid receptors: studies from knockout mice[J]. Prog Lipid Res, 2000, 39(4): 289-314.
  • 4Narumiya S, Sugimoto Y, Ushikubi F. Prostanoid receptors: structures, properties, and functions[J]. Phys Rev, 1999, 79(4): 1 193-1 226.
  • 5Kreydiyyeh S I, Riman S, Serhan M, et al. TNF-alpha modulates hepatic Na^+-K^+ ATPase activity via PGE2 and EP2 receptors[J]. Prostag Oth Lipid Med, 2007, 83(4): 295-303.
  • 6Kimura M, Osumi S, Ogihara M. Prostaglandin E-2 (EP1) receptor agonist-induced DNA synthesis and proliferation in primary cultures of adult rat hepatocytes: The involvement of TGF-alpha[J]. Endocrinology, 2001, 142(10): 4 428-4 440.
  • 7Mater M K, Thelen A P, Jump D B. Arachidonic acid and PGE(2) regulation of hepatic lipogenic gene expression[J]. J Lipid Research, 1999, 40(6): 1 045-1 052.
  • 8Kuhnz W, Hoyer G A, Backhus S. Identification of the major metabolites of the prostaglandin E2-analogue sulprostone in human plasma, and isolation from urine (in vivo) and liver perfusate (in vitro) of female guinea-pigs[J]. Drug Metab Dispos, 1991, 19(5): 920-925.
  • 9Waters N J, Garrod S, Farrant R D, et al. High-resolution magic angle spinning ^1H NMR spectroscopy of intact liver and kidney: Optimization of sample preparation procedures and biochemical stability of tissue during spectral acquisition[J]. Anal Biochem, 2000, 282(1): 16-23.
  • 10vanBaal J, deJong M D, Zijlstra F J, et al. Endogenously produced prostanoids stimulate calcium reabsorption in the rabbit cortical collecting system[J]. J Physiol-London, 1996, 497(1): 229-239.

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