ammonium pyruvate

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 酮酸及其衍生物
• 英文名称: ammonium pyruvate
• 英文别名: Azane;2-oxopropanoic acid；azane;2-oxopropanoic acid
• 化学式: C₃H₄O₃*H₃N
• 分子量: 105.093
• InChiKey: VRYNVZJQBANJOF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  7
• 可旋转键数：
  0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  58.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2,6-二氟苯酚 、 ammonium pyruvate 在 tyrosine-phenol lyase of Citrobacter freundii 、 ammonium acetate 作用下， 反应 336.0h， 生成 3,5-二氟-L-酪氨酸
  参考文献：
  名称：

  Synthesis of 3,5-Difluorotyrosine-Containing Peptides: Application in Substrate Profiling of Protein Tyrosine Phosphatases

  摘要：

  Fully protected 3,5-difluorotyrosine (F2Y), Fmoc-F2Y(tBu)-OH, is efficiently prepared by a chemoenzymatic process and incorporated into individual peptides and combinatorial peptide libraries. The F2Y-containing peptides display kinetic properties toward protein tyrosine phosphatases (PTPs) similar to their corresponding tyrosine-containing counterparts but are resistant to tyrosinase

  DOI：

  10.1021/ol801868a
• 作为产物：
  描述：

  L-丝氨酸 在 磷酸吡哆醛 、 L-lactic dehydrogenase from rabbit muscle 、 recombinant His₆-Schizosaccharomyces pombe serine racemase 、 5’-三磷酸腺苷 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 水 为溶剂， 生成 ammonium pyruvate
  参考文献：
  名称：

  Inhibition of serine and proline racemases by substrate-product analogues

  摘要：

  D-Amino acids can play important roles as specific biosynthetic building blocks required by organisms or act as regulatory molecules. Consequently, amino acid racemases that catalyze the formation of D-amino acids are potential therapeutic targets. Serine racemase catalyzes the reversible formation of D-serine (a modulator of neurotransmission) from L-serine, while proline racemase (an essential enzymatic and mitogenic protein in trypanosomes) catalyzes the reversible conversion of L-proline to D-proline. We show the substrate-product analogue alpha-(hydroxymethyl) serine is a modest, linear mixed-type inhibitor of serine racemase from Schizosaccharomyces pombe (K-i = 167 +/- 21 mM, K-i ' = 661 +/- 81 mM, cf. K-m = 19 +/- 2 mM). The bicyclic substrate-product analogue of proline, 7-azabicyclo[2.2.1]heptan-7-ium-1-carboxylate is a weak inhibitor of proline racemase from Clostridium sticklandii, giving only 29% inhibition at 142.5 mM. However, the more flexible bicyclic substrate-product analogue tetrahydro-1H- pyrrolizine-7a(5H)-carboxylate is a noncompetitive inhibitor of proline racemase from C. sticklandii (K-i = 111 +/- 15 mM, cf. K-m = 5.7 +/- 0.5 mM). These results suggest that substrate-product analogue inhibitors of racemases may only be effective when the active site is capacious and/or plastic, or when the inhibitor is sufficiently flexible. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.10.061
• 作为试剂：
  描述：

  丙酮酸 在 ammonium pyruvate 、 水 作用下， 生成 乳酸 、 meso-2,3-Dimethyl-weinsaeure
  参考文献：
  名称：

  Cathodic Reduction of Negatively Substituted Ketones: α-Ketoacids and β-Ketoesters

  摘要：

  DOI：

  10.1021/jo01101a018

文献信息

• Proton Transfer and Carbon−Carbon Bond Cleavage in the Elimination of Indole Catalyzed by <i>Escherichia coli</i> Tryptophan Indole-Lyase
  作者：Robert S. Phillips、Bakthavatsalam Sundararaju、Nicolai G. Faleev

  DOI：10.1021/ja991647q

  日期：2000.2.1

  Tryptophan indole-lyase from Escherichia coli catalyzes the reversible cleavage of l-tryptophan to indole and ammonium pyruvate. This reaction is mechanistically interesting since it involves the elimination of an aromatic carbon leaving group. We have been studying the mechanism of tryptophan indole-lyase using rapid-scanning stopped-flow spectrophotometry. Recently, we demonstrated that the rate

  来自大肠杆菌的色氨酸吲哚裂解酶催化 l-色氨酸可逆裂解为吲哚和丙酮酸铵。该反应在机理上很有趣，因为它涉及消除芳族碳离去基团。我们一直在使用快速扫描停流分光光度法研究色氨酸吲哚裂解酶的机制。最近，我们证明了由 α-2H-l-色氨酸形成 α-氨基丙烯酸酯中间体的速率常数表现出 3.0 的同位素效应（Sloan, MJ; Phillips, RS Biochemistry 1996, 35, 16165−16173）。我们已经证实了之前的这个结果 (Dk = 2.99 ± 0.30)，我们现在发现 β,β-di-2H-l-色氨酸在消除反应中也表现出二次同位素效应 (Dk = 1.17 ± 0.03)。此外，α,β,β-tri-2H-l-色氨酸表现出多重同位素效应（Dk = 4. 42±0.67）对吲哚的消除。此外，对 D2O 中的吲哚消除有显着的溶剂同位素效应 (Dk = 1.79 ± 0.11)。这种溶剂
• A Potent Pyridoxal Model Capable of Promoting Transamination and β-Elimination of Amino Acids
  作者：Hiroki Kondo、Jun-ichi Kikuchi、Shinji Uchida、Tatsuya Kitamikado、Eiji Koyanagi、Junzo Sunamoto

  DOI：10.1246/bcsj.58.675

  日期：1985.2

  N-Dodecyipyridoxal chloride (1a) has been synthesized as a potent pyridoxal 5′-phosphate model. The equilibrium constant for Schiff base formation of 1a with phenylalanine (21000 M−1) in 3 mM hexadecyltrimethylammonium chloride (CTACl) micelle is over a thousand times larger than that for the N-methyl counterpart (1b). The Schiff base of 1a and phenylalanine exists over a broad pH range of 5–11 in two ionic forms, HSB and SB−, that differ in the protonation state at the azomethine group. These Schiff bases undergo transamination at 30 °C in the absence of a metal ion at considerably different rates; 1.33×10−3 and 1.5×10−5 s−1 for HSB and SB−1, respectively. Likewise, the former species exhibited 11 times higher reactivity in the β-elimination of O-phosphonoserine catalyzed by 1a in 3 mM CTACl at 40 °C. These results indicate unambiguously the importance of a positive charge on the azomethine nitrogen as well as the one residing on the pyridine nitrogen in vitamin B6 catalysis. The kinetic α-deuterium isotope effect of 5.1 in the transamiantion of phenylalanine with 1a at pH 7.7 and 30 °C revealed that α-hydrogen abstraction takes place in the transition state.

  N-十二烷基吡哆醛氯化物 (1a) 已被合成为有效的吡哆醛 5'-磷酸模型。在 3 mM 十六烷基三甲基氯化铵 (CTACl) 胶束中，与苯丙氨酸 (21000 M−1) 形成席夫碱 1a 的平衡常数比 N-甲基对应物 (1b) 大一千倍以上。 1a 和苯丙氨酸的希夫碱以两种离子形式 HSB 和 SB− 存在于 5-11 的宽 pH 范围内，它们在偶氮甲碱基团上的质子化状态不同。这些希夫碱在 30 °C 且不存在金属离子的情况下以相当不同的速率进行氨基转移； HSB 和 SB−1 分别为 1.33×10−3 和 1.5×10−5 s−1。同样，在 40 °C 3 mM CTACl 中 1a 催化的 O-膦酰丝氨酸 β-消除反应中，前一物种表现出高出 11 倍的反应性。这些结果明确表明偶氮甲碱氮上的正电荷以及吡啶氮上的正电荷在维生素 B6 催化中的重要性。在 pH 7.7 和 30 °C 下，5.1 在苯丙氨酸与 1a 转氨基作用中的动力学 α-氘同位素效应表明，α-氢夺取发生在过渡态。
• Properties of tryptophan indole-lyase from a piezophilic bacterium, Photobacterium profundum SS9
  作者：Robert S. Phillips、Rashin Ghaffari、Peter Dinh、Santiago Lima、Douglas Bartlett

  DOI：10.1016/j.abb.2010.11.002

  日期：2011.2

  Tryptophan indole-lyase (Trpase), PBPRA2532, from Photobacterium profundum SS9, a piezophilic marine bacterium, has been cloned, expressed in Escherichia coli, and purified. The P. profundum Trpase (PpTrpase) exhibits similar substrate specificity as the enzyme from E. coli (EcTrpase). PpTrpase has an optimum temperature for activity at about 30 degrees C, compared with 53 degrees C for EcTrpase, and loses activity rapidly (t(1/2) similar to 30 min) when incubated at 50 degrees C, while EcTrpase is stable up to 65 degrees C. PpTrpase retains complete activity when incubated more than 3 h at 0 degrees C, while EcTrpase has only about 20% remaining activity. Under hydrostatic pressure, PpTrpase remains fully active up to 100 MPa (986 atm), while EcTrpase exhibits only about 10% activity at 100 MPa. PpTrpase forms external aldimine and quinonoid intermediates in stopped-flow experiments with L-Trp, S-Et-L-Cys, S-benzyl-L-Cys, oxindolyl-L-Ala, L-Ala and L-Met, similar to EcTrpase. However, with L-Trp a gem-diamine is observed that decays to a quinonoid complex. An aminoacrylate is observed with L-Trp in the presence of benzimidazole, as was seen previously with EcTrpase [28] but not with S-Et-L-Cys. The results show that PpTrpase is adapted for optimal activity in the low temperature, high pressure marine environment. (C) 2010 Elsevier Inc. All rights reserved.
• Polypeptides and biosynthetic pathways
  申请人：CARGILL, INCORPORATED

  公开号：EP2354240B1

  公开（公告）日：2016-07-06
• Ashiuchi, Makoto; Yoshimura, Tohru; Esaki, Nobuyoshi, Bioscience, Biotechnology and Biochemistry, 1993, vol. 57, # 11, p. 1978 - 1979
  作者：Ashiuchi, Makoto、Yoshimura, Tohru、Esaki, Nobuyoshi、Ueno, Esaki、Soda, Kenji

  DOI：——

  日期：——