(1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure | 84601-12-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure
• 英文别名: (1R,2R)-(2-amino-1-hydroxypropyl)-phosphonic acid；(1R,2R)-(2-amino-1-hydroxypropyl)phosphonic acid；(1R,2R)-2-amino-1-hydroxypropylphosphonic acid；(R,R)-2-amino-1-hydroxypropylphosphonic acid；2-Amino-1-hydroxypropylphosphonsaeure；[(1R,2R)-2-amino-1-hydroxypropyl]phosphonic acid
• CAS: 84601-12-7
• 化学式: C₃H₁₀NO₄P
• 分子量: 155.09
• InChiKey: UEQTWCFLYPSNIA-PWNYCUMCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4.9
• 重原子数：
  9
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure 在 PhnZ Fe(II)-dependent phosphohydrolase 作用下， 生成 (R)-(1-hydroxyethyl)phosphonic acid
  参考文献：
  名称：

  PhnZ 与底物复合的晶体结构揭示了有机膦酸盐分解代谢的二铁加氧酶机制。

  摘要：

  PhnY 和 PhnZ 酶包含氧化分解代谢途径，使海洋细菌能够使用 2-氨基乙基膦酸作为无机磷酸盐的来源。PhnZ 以使用 Fe(II) 和双氧催化碳-磷键的氧化裂解而著称，尽管它属于水解酶的一个大家族，即 HD-磷酸水解酶超家族。我们已经确定了与其底物 (R)-2-amino-1-hydroxyethylphosphonate (2.1 A) 和缓冲添加剂 l-酒石酸盐 (1.7 A) 结合的 PhnZ 的高分辨率结构。这些结构表明 PhnZ 具有一个活性位点，其中包含由四个组氨酸和两个天冬氨酸配位的两个 Fe 离子，与碳-碳键裂解酶肌肉肌醇加氧酶极为相似。Y24 是个例外，它在 Fe2 的双氧结合位点形成瞬时配体相互作用。用底物类似物进行定点诱变和动力学分析揭示了关键活性位点残基的作用。第五个组氨酸在 PhnZ 亚分支中保守，H62，专门与底物 1-羟基相互作用。这些结构还表明，Y24

  DOI：

  10.1073/pnas.1320039111
• 作为产物：
  描述：

  (1-deuterio-1,2-dihydroxyethyl)phosphonic acid 在 氨 作用下， 生成 (1R,2R)-(-)-(2-Amino-1-hydroxypropyl)phosphonsaeure
  参考文献：
  名称：

  Biosynthesis of natural products with a phosphorus-carbon bond. 7. Synthesis of [1,1-2H2]-, [2,2-2H2]-, (R)- and (S)-[1-2H1](2-hydroxyethyl)phosphonic acid and (R,S)-[1-2H1](1,2-dihydroxyethyl)phosphonic acid and incorporation studies into fosfomycin in Streptomyces fradiae

  摘要：

  Nondeuteriated and deuteriated 2-(benzyloxy)ethanols (8a-c) were transformed into (2-hydroxyethyl)phosphonic acids (12a-c). 8c was prepared from dimethyl 2,3-O-isopropylidene-L-tartrate. 12b,c were fed to Streptomyces fradiae and were incorporated into fosfomycin (2), which was converted to amino phosphonic acid (-)-13. (-)-13 derived from 12b,c contained 42% and 34% deuterium, respectively. (1,2-Dihydroxyethyl)phosphonic acid ((+/-)-29) was not incorporated into fosfomycin. (S)- and (R)-(2-hydroxy[1-H-2-1]ethyl)phosphonic acids ((S)- and (R)-34) were prepared from (S)-2-(benzyloxy)[1-H-2-1]ethanol ((S)-30) and fed to S. fradiae. The deuterium of (R)-34 was lost, and the deuterium of (S)-34 was retained on incorporation into fosfomycin. The optical purity of (S)- and (R)-34 (84% and 86%, respectively) was determined by transformation to dimethyl ester and esterification with (+)-MTPA-Cl to afford 39b,c. 41 obtained from (S)-32 was identical with an authentic sample prepared from (S)-(2-amino[1-H-2-1]ethyl)phosphonic acid.

  DOI：

  10.1021/jo00007a022

文献信息

• Towards the biodegradation pathway of fosfomycin
  作者：K. Pallitsch、A. Schweifer、A. Roller、F. Hammerschmidt

  DOI：10.1039/c7ob00546f

  日期：——

  conversion into its 2-oxo derivative in the cell, was accessed from trifluoroacetaldehyde hydrate via hydroxypropanenitrile 21, which was silylated and reduced to the aldehyde (±)-23. Diastereoselective addition of diethyl trimethylsilyl phosphite furnished diastereomeric α-siloxyphosphonates. The less polar one was converted to the desired racemic phosphonic acid (±)-(1R*,2R*)-9 as its ammonium salt.

  合成了三种功能化的丙基膦酸，以研究华氏疟原虫PMY1中的C-P键裂解。（R）-1-羟基-2-氧代丙基膦酸[（R）-5 ]是通过手性拆分（±）-二甲基1-羟基-2-甲基烯丙基膦酸酯[（±）-12 ]制备的，然后进行臭氧分解和脱保护。 。所述ñ - （大号-丙氨酰） -取代的（1 - [R，2 - [R）-2-氨基-1- hydroxypropylphosphonic酸10，为2-氧代丙基膦（潜在的前体5中的细胞），是由氨基膦酸与偶合得到苯并三唑激活ž -L-丙氨酸和氢解脱保护。从三氟乙醛中获得了（1 R *，2 R *）-1,2-二羟基-3,3,3-三氟丙基膦酸（一种转化为细胞中的2-氧代衍生物后潜在的C-P键断裂的抑制剂）通过羟基丙腈21进行水合，甲硅烷化并还原成醛（±）-23。亚磷酸二乙基三甲基甲硅烷基酯的非对映选择性加成得到非对映异构体α-甲硅烷氧基膦酸酯。极性较小的铵盐以其铵盐的形式转化为所需的外消旋膦酸（±）-（1
• Hammerschmidt, Friedrich, Liebigs Annalen der Chemie, 1992, # 6, p. 553 - 558
  作者：Hammerschmidt, Friedrich

  DOI：——

  日期：——
• Simov, Biljana Peric; Wuggenig, Frank; Laemmerhofer, Michael, European Journal of Organic Chemistry, 2002, # 7, p. 1139 - 1142
  作者：Simov, Biljana Peric、Wuggenig, Frank、Laemmerhofer, Michael、Lindner, Wolfgang、Zarbl, Elfriede、Hammerschmidt, Friedrich

  DOI：——

  日期：——
• Hammerschmidt, Friedrich; Bovermann, Guenther; Bayer, Karl, Liebigs Annalen der Chemie, 1990, # 11, p. 1055 - 1061
  作者：Hammerschmidt, Friedrich、Bovermann, Guenther、Bayer, Karl

  DOI：——

  日期：——
• On the conversion of structural analogues of (S)-2-hydroxypropylphosphonic acid to epoxides by the final enzyme of fosfomycin biosynthesis in S. fradiae
  作者：Anna Schweifer、Friedrich Hammerschmidt

  DOI：10.1016/j.bmcl.2007.12.012

  日期：2008.5

  2-Hydroxyethyl- and (S)-2-hydroxybutylphosphonic acid were prepared, starting in the latter case from (S)-2-aminobutyric acid. They were fed to cultures of Streptomyces fradiae producing fosfomycin. Only the latter (150 mu g/mL of medium) was converted to the ethyl analogue of fosfomycin, isolated as 2-amino-1-hydroxybutylphosphonic acid (3%)in admixture with 2-amino-1-hydroxypropylphosphonic acid (97%) derived from fosfomycin. (c) 2008 Elsevier Ltd. All rights reserved.