N-草酰-L-丙氨酸 | 5302-46-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 中文名称: N-草酰-L-丙氨酸
• 英文名称: N-oxalyl-2S-alanine
• 英文别名: N-oxalyl-L-alanine；N-oxalylalanine；oxalyl-L-alanine；N-oxalo-(S)-alanine；(S)-2-(Carboxyformamido)Propanoic Acid；(2S)-2-(oxaloamino)propanoic acid
• CAS: 5302-46-5
• 化学式: C₅H₇NO₅
• 分子量: 161.114
• InChiKey: TZPZMVZGJVYAML-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-草酰-L-丙氨酸 在 盐酸 作用下， 以 水 为溶剂， 反应 13.0h， 生成 L-丙氨酸
  参考文献：
  名称：

  Sarmentosamide, a novel hexadienamide from Thai soil actinomycetes

  摘要：

  A new hexadienamide derivative named sarmentosamide (1) was identified from the culture of Streptomyces sp. SBI108 isolated from Thai soil under an herb. The structure was elucidated on the basis of spectroscopic data, and the absolute configuration was determined by chemical degradation.

  DOI：

  10.1080/14786419.2012.671313
• 作为产物：
  描述：

  methoxyoxalylalanine methyl ester 在 sodium hydroxide 作用下， 生成 N-草酰-L-丙氨酸
  参考文献：
  名称：

  选择性抑制因子抑制缺氧诱导因子

  摘要：

  一组四种非血红素铁 (II) 和 2-氧戊二酸依赖性酶催化转录因子、缺氧诱导因子 (HIF) 的翻译后修饰，该转录因子介导动物的缺氧反应。HIF 的羟基化会导致其降解并限制其活性。我们描述了如何使用与固相合成耦合的结构数据导致发现一种 HIF 羟化酶的选择性抑制剂。抑制剂 N-草酰-d-苯丙氨酸显示抑制 HIF 天冬酰胺酰羟化酶 (FIH) 但不抑制 HIF 脯氨酰羟化酶。与 FIH 复合的抑制剂的晶体结构表明它与 2OG 结合，并且很可能与分子氧结合位点结合。该结果将有助于调节缺氧反应，以上调具有生物医学重要性的特定基因，

  DOI：

  10.1021/ja050841b

文献信息

• Iron-Mediated Cleavage of CC Bonds in Vicinal Tricarbonyl Compounds in Water
  作者：Jasmin Mecinović、Refaat B. Hamed、Christopher J. Schofield

  DOI：10.1002/anie.200806296

  日期：2009.3.30

  Three of a kind: Vicinal tricarbonyl compounds undergo CC cleavage mediated by ferric ions (see scheme). The observed cleavage of ninhydrin and dehydroascorbic acid has relevance for amino acid detection and the metabolism of vitamin C.

  一种三邻位三羰基化合物经历C： Ç裂解通过三价铁离子（参见方案）介导的。观察到的茚三酮和脱氢抗坏血酸的裂解与氨基酸检测和维生素C的代谢有关。
• Novel inhibitors of prolyl 4-hydroxylase. 3. Inhibition by the substrate analog N-oxaloglycine and its derivatives
  作者：C. Jane Cunliffe、Trevor J. Franklin、Neil J. Hales、George B. Hill

  DOI：10.1021/jm00092a016

  日期：1992.7

  N-Oxaloglycine (3) is an alpha-ketoglutarate (1) analogue that is a competitive inhibitor of prolyl 4-hydroxylase (EC 1.14.11.2). A study of the structure-activity relationships of some other oxalo derivatives shows that substitution on the glycine moiety modulates activity stereoselectively and that if the omega-carboxylate is homologated or replaced by either acylsulfonamides or anilide, then activity is sharply reduced. This sensitivity to these changes is contrasted with the relative insensitivity of another putative alpha-ketoglutarate analogue, pyridine-2,5-dicarboxylic acid (2), and the implication is discussed that compounds of both series are unlikely to bind to prolyl hydroxylase in the same way even though both inhibit the enzyme competitively.
• Selective Inhibition of Factor Inhibiting Hypoxia-Inducible Factor
  作者：Michael A. McDonough、Luke A. McNeill、Melanie Tilliet、Cyril A. Papamicaël、Qiu-Yun Chen、Biswadip Banerji、Kirsty S. Hewitson、Christopher J. Schofield

  DOI：10.1021/ja050841b

  日期：2005.6.1

  transcription factor, hypoxia inducible factor (HIF), that mediates the hypoxic response in animals. Hydroxylation of HIF both causes its degradation and limits its activity. We describe how the use of structural data coupled to solid-phase synthesis led to the discovery of a selective inhibitor of one of the HIF hydroxylases. The inhibitor N-oxalyl-d-phenylalanine was shown to inhibit the HIF asparaginyl

  一组四种非血红素铁 (II) 和 2-氧戊二酸依赖性酶催化转录因子、缺氧诱导因子 (HIF) 的翻译后修饰，该转录因子介导动物的缺氧反应。HIF 的羟基化会导致其降解并限制其活性。我们描述了如何使用与固相合成耦合的结构数据导致发现一种 HIF 羟化酶的选择性抑制剂。抑制剂 N-草酰-d-苯丙氨酸显示抑制 HIF 天冬酰胺酰羟化酶 (FIH) 但不抑制 HIF 脯氨酰羟化酶。与 FIH 复合的抑制剂的晶体结构表明它与 2OG 结合，并且很可能与分子氧结合位点结合。该结果将有助于调节缺氧反应，以上调具有生物医学重要性的特定基因，
• Sarmentosamide, a novel hexadienamide from Thai soil actinomycetes
  作者：Shigeru Kitani、Ayako Tomio、Akkaraphol Srichaisupakit、Ratama Daduang、Bungonsiri Intra、Watanalai Panbangred、Naoya Oku、Yasuhiro Igarashi、Takuya Nihira

  DOI：10.1080/14786419.2012.671313

  日期：2013.2.1

  A new hexadienamide derivative named sarmentosamide (1) was identified from the culture of Streptomyces sp. SBI108 isolated from Thai soil under an herb. The structure was elucidated on the basis of spectroscopic data, and the absolute configuration was determined by chemical degradation.