(L-Ala)3-L-Ala(P) | 65621-21-8

• 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: (L-Ala)3-L-Ala(P)
• 英文别名: (1R)-1-(L-alanyl-L-alanyl-L-alanylamino)-ethylphosphonic acid；[(1R)-1-[[(2S)-2-[[(2S)-2-[[(2S)-2-aminopropanoyl]amino]propanoyl]amino]propanoyl]amino]ethyl]phosphonic acid
• CAS: 65621-21-8
• 化学式: C₁₁H₂₃N₄O₆P
• 分子量: 338.301
• InChiKey: WPCOBVVKSMAEAI-DKXJUACHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  171
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (L-Ala)3-L-Ala(P) 在 sodium hydroxide 作用下， 以1.0 g的产率得到phosphonic acid
  参考文献：
  名称：

  Synthesis and structure-activity relationships of antibacterial phosphonopeptides incorporating (1-aminoethyl)phosphonic acid and (aminomethyl)phosphonic acid

  摘要：

  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.

  DOI：

  10.1021/jm00151a005

文献信息

• Process for influencing plant growth
  申请人：CIBA-GEIGY AG

  公开号：EP0010067A2

  公开（公告）日：1980-04-16

  An agent for influencing plant growth, in particular a herbicidal and plant growth inhibiting agent, contains, in addition to carriers and/or other additives, at least one compound of the formula:- or the corresponding zwitterion form in which R and R1 may be the same or different and each can be hydrogen, deuterium or an optionally substituted lower alkyl group, lower alkenyl, lower alkynyl, cycloalkyl, aryl or heterocyclic radical containing one or more oxygen, nitrogen or sulphur atoms and which may be fused to an aromatic ring, a lower alkyl group substituted by a cycloalkyl radical, a lower alkyl group substituted by an aryl radical, a lower alkyl group substituted by a heterocyclic radical as defined above, or R and R together form a polymethylene chain optionally interrupted by an oxygen, nitrogen or sulphur atoms, or R represents, together with the C(R)-N < residue to which it is attached, the atoms required to complete a heterocyclic radical; and R2 and R3 may be the same or different and each can be hydrogen, optionally substituted lower alkyl, cycloalkyl, aryl or lower alkyl substituted by a heterocyclic radical containing one or more nitrogen atom; a heterocyclic radical containing one or more nitrogen atoms; or R2 and R3, independently, together with the C(H)-N residue to which each is attached, may each represent the atoms required to complete a heterocyclic radical; R. is OH CH3; or phenyl; R7 is hydrogen or an alkoxycarbonyl or benzyloxycarbonyl group; and n is 0, 1, 2 or 3; as well as the esters or partial esters thereof with physiologically splittable alcohols; salts of the compounds of formula I, or their esters or partial esters with acids or bases physiologically acceptable to plants, respectively; and all optical isomers thereof.

  一种影响植物生长的制剂，特别是一种除草剂和植物生长抑制剂，除载体和/或其他添加剂外，还含有至少一种式如下的化合物 或相应的齐聚物形式，其中 R 和 R1 可以相同或不同，并且各自可以是氢、氘或任选取代的低级烷基、低级烯基、低级炔基、环烷基、芳基或杂环基，这些基团含有一个或多个氧原子、氮原子或硫原子，并可与芳香环融合；被环烷基取代的低级烷基、被芳基取代的低级烷基、被上文定义的杂环基取代的低级烷基，或 R 和 R 共同形成可选择被氧、氮或硫原子打断的多亚甲基链，或 R 与所连接的 C(R)-N < 残基一起代表完成杂环基所需的原子；和 R2 和 R3 可以相同或不同，各自可以是氢、任选取代的低级烷基、环烷基、芳基或被含一个或多个氮原子的杂环基取代的低级烷基；含一个或多个氮原子的杂环基；或 R2 和 R3 与各自所连接的 C(H)-N 残基一起独立地各自代表完成一个杂环基所需的原子；R.是 OH CH3；或苯基；R7 是氢或烷氧羰基或苄氧羰基；n 是 0、1、2 或 3；以及其与生理上可拆分的醇的酯或部分酯；式 I 化合物或其酯或部分酯分别与植物生理上可接受的酸或碱的盐，以及其所有光学异构体。
• Process for producing alpha-aminophosphonic acids and their peptides and compounds thus obtained
  申请人：CIBA-GEIGY AG

  公开号：EP0010872B1

  公开（公告）日：1983-05-25
• SELECTIVE GROWTH MEDIA
  申请人：The Newcastle upon Tyne Hospitals National Health Service Trust

  公开号：EP1325024B1

  公开（公告）日：2011-04-20
• US4100275A
  申请人：——

  公开号：US4100275A

  公开（公告）日：1978-07-11
• US4127649A
  申请人：——

  公开号：US4127649A

  公开（公告）日：1978-11-28