p-dimethylphosphonomethyl-L-phenylalanine methyl ester hydrochloride | 140866-80-4

• 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: p-dimethylphosphonomethyl-L-phenylalanine methyl ester hydrochloride
• 英文别名: p-Dimethylphosphonomethyl-L-phenylalanyl methyl ester hydrochloride
• CAS: 140866-80-4
• 化学式: C₁₃H₂₀NO₅P*ClH
• 分子量: 337.74
• InChiKey: CPCABCVHJUYFHQ-YDALLXLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.14
• 重原子数：
  21.0
• 可旋转键数：
  7.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  87.85
• 氢给体数：
  1.0
• 氢受体数：
  6.0

反应信息

• 作为产物：
  描述：

  (4-bromo-methylbenzyl)phosphonic acid dimethyl ester 在 盐酸 、 正丁基锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 为溶剂， 反应 8.0h， 生成 p-dimethylphosphonomethyl-L-phenylalanine methyl ester hydrochloride
  参考文献：
  名称：

  Synthesis of p-Phosphonomethyl-L-phenylalanine using Camphor Sultam or D-Valine as Chiral Auxiliaries and its Incorporation into Integrin Sequences.

  摘要：

  The synthesis of N-Boc-p-phosphonomethyl-L-phenylalanine with two different chiral auxiliaries, camphor sultam or D-valine is described. The preparations have essentially identical properties and have been used to incorporate the amino acid into two integrin peptides as non-hydrolyzable isosteres of phosphotyrosine.

  DOI：

  10.3891/acta.chem.scand.50-0054

文献信息

• Preparation of an angiotensin i analog containing a p-phosphonomethyl-l-phenylalanine residue via asymmetric synthesis of t-boc-p- dimethylphosphonomethyl-l-phenylalanine
  作者：Mark Cushman、Eung-Seok Lee

  DOI：10.1016/s0040-4039(00)91893-8

  日期：1992.2

  t-BOC-p-Dimethylphosphonomethyl-L-phenylalanine has been prepared and incorporated into a peptide sequence corresponding to angiotensin I. Demethylation of the dimethylphosphonomethyl moiety then yielded a peptide containing a p-phosphonomethyl-L-phenylalanine residue.