(+)-(S)-<1-amino-2-hydroxyethyl>phosphonic acid | 90427-79-5

• 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: (+)-(S)-<1-amino-2-hydroxyethyl>phosphonic acid
• 英文别名: (+)-(S)-(1-amino-2-hydroxyethyl)phosphonic acid；(S)-(+)-(1-Amino-2-hydroxyethyl)phosphonsaeure；(S)-1-Amino-2-hydroxyethanephosphonic acid；S(+)SerP；[(1S)-1-amino-2-hydroxyethyl]phosphonic acid
• CAS: 90427-79-5
• 化学式: C₂H₈NO₄P
• 分子量: 141.064
• InChiKey: RVUUAGQILBTWHJ-REOHCLBHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.3
• 重原子数：
  8
• 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

• 作为产物：
  描述：

  (+)-(S)-diethyl (1-amino-2-hydroxyethyl)phosphonate 在 盐酸 作用下， 以 水 为溶剂， 反应 15.0h， 以91%的产率得到(+)-(S)-<1-amino-2-hydroxyethyl>phosphonic acid
  参考文献：
  名称：

  N-糖基硝酮的亲核加成。α-氨基膦酸的不对称合成† ‡

  摘要：

  这解释了的1,3-偶极环加成的非对映选择性的假说Ñ -glycosylnitrones 1 - 3通向5,5-二取代的异恶唑烷4 - 6的动能端基异构效应的基础上预测，亲核试剂应该添加到ñ -具有高度非对映选择性的糖基硝酮。为了检验该预测，已经研究了锂和二烷基亚磷酸锂向由肟9和（苄氧基）乙醛制备的结晶（Z）-硝基1的亲核加成反应。亚磷酸锂的添加使N-glycosyl- Ñ -hydroxyaminophosphonates 12 - 16（78-92 DE％）以高收率（方案4） 。亚磷酸钾的添加显示出低得多的非对映选择性。糖苷切割，氢解，和脱烷基化的12 - 16得到（+） - （小号）-phosphoserine（+） - 19（34-45％来自9）。通过N-（3,3,3-三氟-2-甲氧基-2-甲氧基-2-苯基丙酰）衍生物24的X射线分析证实了其绝对构型。类似地，结晶的硝酮25得到N-糖

  DOI：

  10.1002/hlca.19850680629

文献信息

• Nucleophilic additions toN-glycosylnitrones part IV Asymmetric synthesis ofN-hydroxy-?-aminophosphonic and ?-aminophosphonic acids
  作者：Rolf Huber、Andrea Vasella

  DOI：10.1002/hlca.19870700603

  日期：1987.9.23

  proved inert towards the phosphite anions, they reacted with P(OSiMe3)3 under catalysis by Lewis acids. Thus, P(OSiMe3)3 reacted with the crystalline (Z)-N-glycosylnitrones 2 and 8 to give the optically active N-hydroxy-α-aminophosphonic acids 4 and 10, respectively, and hence the α-aminophosphonic acids 5 and 11 in yields up to 92% and with an enantiomeric excess (e.e.) up to 97% (Scheme 1). The absolute

  添加亚磷酸阴离子和三（三甲基硅烷基）亚磷酸酯（P（OSiMe 3）3），以Ñ -glycosyl- Ç -arylnitrones检查。尽管这些硝酮对亚磷酸根阴离子呈惰性，但它们在路易斯酸催化下与P（OSiMe 3）3反应。因此，P（OSiMe 3）3与结晶的（Z）-N-糖基硝酮2和8反应，得到旋光的N-羟基-α-氨基膦酸4和10。因此，α-氨基膦酸5和11的产率最高为92％，对映体过量（ee）最高为97％（方案1）。膦酸酯的绝对构型取决于性质，在一种情况下取​​决于催化剂的量（图）。在HCIO 4或Zn（OTF）2催化下，将p（OSiMe 3）3添加到2中，在两种情况下均得到（+）-（R）-苯基磷酸甘氨酸5（光学纯度分别为79–84和90–93％）。光学纯度（op）几乎不受这些催化剂的量（0.02-； 1当量）的影响。但是，用ZnCl 2催化可得到痕量的催化剂，（-）-（S）-5（op 79％），而等摩尔量的ZnCl
• Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid
  作者：Frank R. Atherton、Cedric H. Hassall、Robert W. Lambert

  DOI：10.1021/jm00151a005

  日期：1986.1

  Phosphonodipeptides and phosphonooligopeptides based on L- and D-(1-aminoethyl)phosphonic acids L-Ala(P) and D-Ala(P) and (aminomethyl)phosphonic acid Gly(P) at the acid terminus have been synthesized and investigated as antibacterial agents, which owe their activity to the inhibition of bacterial cell-wall biosynthesis. A method for large-scale synthesis of the potent antibacterial agent L-Ala-L-Ala(P) (1, Alafosfalin) is described. Structure-activity relationships in the dipeptide series have been studied by systematic variation of structure 1. L stereochemistry is generally required for both components. Changes in the L-Ala(P) moiety mostly lead to loss of antibacterial activity, but the phosphonate analogues of L-phenylalanine, L-Phe(P), and L-serine, L-Ser(P), give rise to weakly active L-Ala-L-Phe(P) and L-Ala-L-Ser(P). Replacement of L-Ala in 1 by common and rare amino acids can give rise to more potent in vitro antibacterials such as L-Nva-L-Ala(P) (45). Synthetic variation of these more potent dipeptides leads to decreased activity. Phosphonooligopeptides such as (L-Ala)2-L-Ala(P) have a broader in vitro antibacterial spectrum than their phosphonodipeptide precursor, but this is not expressed in vivo, presumably due to rapid metabolism to 1. Stabilized compounds such as Sar-L-Nva-L-Nva-L-Ala(P) (46) have been developed that are more potent in vivo and have a broader in vivo antibacterial spectrum than the parent phosphonodipeptide.
• Synthesis of the Phosphonic Acid Analog of Serine
  作者：Barbara Lejczak、Paweł Kafarski、Mirosław Soroka、Przemysław Mastalerz

  DOI：10.1055/s-1984-30897

  日期：——
• Hammerschmidt, Friedrich; Voellenkle, Horst, Liebigs Annalen der Chemie, 1989, p. 577 - 584
  作者：Hammerschmidt, Friedrich、Voellenkle, Horst

  DOI：——

  日期：——
• Kowalik, Janusz; Zygmunt, Jan; Mastalerz, Przemyslaw, Phosphorus and Sulfur and the Related Elements, 1983, vol. 18, p. 393 - 396
  作者：Kowalik, Janusz、Zygmunt, Jan、Mastalerz, Przemyslaw

  DOI：——

  日期：——