N-t-Boc-p-dimethylphosphonomethyl-L-phenylalanine | 140866-82-6

• 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-t-Boc-p-dimethylphosphonomethyl-L-phenylalanine
• 英文别名: Boc-p-dimethylphosphonylmethyl-L-phenylalanine；Boc-Phe(4-CH2PO(OMe)2)-OH；(2S)-3-[4-(dimethoxyphosphorylmethyl)phenyl]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 140866-82-6
• 化学式: C₁₇H₂₆NO₇P
• 分子量: 387.37
• InChiKey: ATSSJGUWZDAYEB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  26
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N-t-Boc-p-dimethylphosphonomethyl-L-phenylalanine 生成
  参考文献：
  名称：

  Preparation of an angiotensin i analog containing a p-phosphonomethyl-l-phenylalanine residue via asymmetric synthesis of t-boc-p- dimethylphosphonomethyl-l-phenylalanine

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)91893-8
• 作为产物：
  描述：

  (2R,2S')-N--p-dimethylphosphonomethylphenylalaninyl>bornane-10,2-sultam 在 盐酸 、 lithium hydroxide 、 sodium carbonate 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 水 为溶剂， 反应 11.0h， 生成 N-t-Boc-p-dimethylphosphonomethyl-L-phenylalanine
  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

• [EN] PEPTIDE ANTAGONISTS OF SH2 BINDING AND THERAPEUTIC USES THEREOF<br/>[FR] ANTAGONISTES PEPTIDIQUES DE LA FIXATION DU SH2 ET LEURS USAGES THERAPEUTIQUES
  申请人：WARNER-LAMBERT COMPANY

  公开号：WO1994007913A1

  公开（公告）日：1994-04-14

  (EN) Peptide compounds that antagonize the association of a protein tyrosin kinase with substrate regulatory protein and that incorporate the tyrosine autophosphorylation site of a receptor tyrosine kinase in its phosphorylated form, salts thereof, methods of production, pharmaceutical compositions containing said compounds and methods for treating proliferative disease using said compositions are disclosed.(FR) L'invention se rapporte à des composés peptidiques antagonistes de l'association d'une tyrosine kinase avec une protéine régulatrice et qui contiennent le site d'autophosphorylation de la tyrosine d'une tyrosine kinase réceptrice sous sa forme phosphorylée, à des sels de ces derniers, à des procédés de production, à des compositions pharmaceutiques contenant lesdits composés et à des procédés de traitement de maladies proliférantes utilisant lesdites compositions.
• Synthesis of p-Phosphonomethyl-L-phenylalanine using Camphor Sultam or D-Valine as Chiral Auxiliaries and its Incorporation into Integrin Sequences.
  作者：Elisabeth Larsson、Björn Lüning、Klaus Bechgaard、Jon Songstad、Markku Leskelä、Mika Polamo、Muhammed Nour Homsi、Frank K. H. Kuske、Monika Haugg、Nathalie Trabesinger-Rüf、Elmar G. Weinhold

  DOI：10.3891/acta.chem.scand.50-0054

  日期：——

  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.
• 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.