N-(carboxymethyl)phophoroamidate | 67278-70-0

• 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
• 英文名称: N-(carboxymethyl)phophoroamidate
• 英文别名: N-(carboxymethyl)phosphoramidate
• CAS: 67278-70-0
• 化学式: C₂H₃NO₅P*3Na
• 分子量: 220.993
• InChiKey: XIZARURLSVDDTR-UHFFFAOYSA-K

计算性质

• 辛醇/水分配系数(LogP)：
  -6.84
• 重原子数：
  10.0
• 可旋转键数：
  3.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  115.35
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  N-bis(9-uorenylmethyl)phosphorylglycine methyl ester 在 sodium hydroxide 作用下， 以 1,4-二氧六环 、 水 为溶剂， 生成 N-(carboxymethyl)phophoroamidate
  参考文献：
  名称：

  关于假定为中间体的环状酰基磷酰胺 (CAPA) 的亲电性

  摘要：

  科技部[2006DFA43030]；国家自然科学基金 [20732004]

  DOI：

  10.1002/ejoc.200900227

文献信息

• N-phosphorylation of amino acids by trimetaphosphate in aqueous solution—learning from prebiotic synthesis
  作者：Feng Ni、Shuting Sun、Chao Huang、Yufen Zhao

  DOI：10.1039/b817013d

  日期：——

  Inspired by a reactivity study between sodium trimetaphosphate (P3m) and amino acids in prebiotic chemistry, a one-step reaction with efficient purification procedure in aqueous media has been developed for the synthesis of N-phosphono-amino acids (NPAA). P3m was used to phosphorylate amino acids to NPAA with yields of 60∼91%. The by-products, inorganic polyphosphates, were recycled to regenerate the phosphorylation reagent P3m.

  受到三偏磷酸钠（P3m）与氨基酸在生物前化学中反应性研究的启发，我们开发了一种在水介质中一步反应、高效纯化的方法来合成 N-膦酰基氨基酸（NPAA）。利用 P3m 将氨基酸磷酸化为 NPAA，产率为 60¼91%。副产品无机多磷酸盐被回收用于再生磷酸化试剂 P3m。
• Formation of Dipeptide in the Reaction of Amino Acids with cyclo-Triphosphate.
  作者：Hideko INOUE、Yoshinobu BABA、Tomoko FURUKAWA、Yasuyo MAEDA、Mitsutomo TSUHAKO

  DOI：10.1248/cpb.41.1895

  日期：——

  The reaction of glycine (Gly) or L-α-alanine (Ala) with inorganic sodium cyclo-triphosphate hexahydrate (P3m), Na3P3O9·6H2O gave dipeptides and the phosphorylated products of amino acids, but the reaction of L-valine (Val) or L-serine (Ser) with P3m showed no peptide formation. The phosphorylated products of these reactions have a P-N bond in their molecules. Gly reacted with P3m to give N-(carboxymethyl)phosphoramidate (P1(N)Gly : 1a), 5-oxo-1, 3, 2-oxazaphospholidin-2-olate 2-oxide (P1(N, O)Gly : 2a), which was a five-membered cyclic anhydride, N-(N-phosphonoglycyl)glycine (P1-N(GlyGly) : 3a), N-(carboxymethyl)triphosphoramidate (P3(N)Gly : 4a), and glycyl-glycine (GlyGly). A five-membered cyclic anhydride (2a) which was formed via an intramolecular cyclization of 4a was found to be a key intermediate for the production of GlyGly. Phosphorylation of Ala with P3m also gave alanylalanine (AlaAla) in addition to the phosphorylated products including a five-membered cyclic anhydride. The yields of GlyGly and AlaAla were 15.8 and 2.0%, respectively. In the reactions of Val and Ser with P3m, only N-(1-carboxy-2-methylpropyl)phosphoramidate (P1-(N)Val : 1c) and N-(1-carboxy-2-hydroxyethyl)phosphoramidate (P1-(N)Ser : 1d) were formed and their dipeptides were not obtained at all. The mechanism of the dipeptide formation will be discussed.

  甘氨酸（Gly）或L-α-丙氨酸（Ala）与无机环三磷酸钠六水合物（P3m）Na3P3O9·6H2O反应生成二肽和氨基酸的磷酸化产物，但L-缬氨酸（Val）反应生成或 L-丝氨酸 (Ser) 与 P3m 未显示肽形成。这些反应的磷酸化产物的分子中具有 P-N 键。 Gly 与 P3m 反应，得到 N-(羧甲基)氨基磷酸酯 (P1(N)Gly : 1a), 5-oxo-1, 3, 2-oxaza磷脂-2-油酸酯 2-氧化物 (P1(N, O)Gly : 2a ），它是五元环酸酐、N-(N-膦酰基甘氨酰)甘氨酸 (P1-N(GlyGly) : 3a)、N-(羧甲基)三氨基磷酸酯 (P3(N)Gly : 4a) 和甘氨酰甘氨酸（甘氨酸）。通过 4a 分子内环化形成的五元环酸酐 (2a) 被发现是生产 GlyGly 的关键中间体。 Ala 用 P3m 磷酸化除了产生包括五元环酸酐的磷酸化产物外，还产生丙氨酰丙氨酸 (AlaAla)。 GlyGly和AlaAla的产率分别为15.8%和2.0%。在Val和Ser与P3m的反应中，只有N-(1-羧基-2-甲基丙基)氨基磷酸酯(P1-(N)Val : 1c)和N-(1-羧基-2-羟乙基)氨基磷酸酯(P1-( N)Ser：1d)形成，但根本没有获得它们的二肽。将讨论二肽形成的机制。
• Tsuhako, Mitsumoto; Ohashi, Shigeru; Nariai, Hiroyuki, Chemical and pharmaceutical bulletin, 1982, vol. 30, # 11, p. 3882 - 3889
  作者：Tsuhako, Mitsumoto、Ohashi, Shigeru、Nariai, Hiroyuki、Motooka, Itaru

  DOI：——

  日期：——