α-methyl 4-sulfophenylalanine | 1270505-58-2

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 苯丙酸
• 英文名称: α-methyl 4-sulfophenylalanine
• 英文别名: 2-Amino-2-methyl-3-(4-sulfophenyl)propanoic acid
• CAS: 1270505-58-2
• 化学式: C₁₀H₁₃NO₅S
• 分子量: 259.283
• InChiKey: SMKGUEAXUZYCRE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.5
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  126
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  alpha-甲基-DL-苯丙氨酸 在 硫酸 作用下， 生成 α-methyl 4-sulfophenylalanine
  参考文献：
  名称：

  Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system over the vesicular glutamate transporter

  摘要：

  A panel of amino acid analogs and conformationally-restricted amino acids bearing a sulfonic acid were synthesized and tested for their ability to preferentially inhibit the obligate cysteine-glutamate transporter system x(c)(-) versus the vesicular glutamate transporter (VGLUT). Several promising candidate molecules were identified: R/S-4-[4'-carboxyphenyl]-phenylglycine, a biphenyl substituted analog of 4-carboxyphenylglycine and 2-thiopheneglycine-5-sulfonic acid both of which reduced glutamate uptake at system x(c)(-) by 70-75% while having modest to no effect on glutamate uptake at VGLUT. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.10.020

文献信息

• Conformationally-restricted amino acid analogues bearing a distal sulfonic acid show selective inhibition of system over the vesicular glutamate transporter
  作者：Jean-Louis G. Etoga、S. Kaleem Ahmed、Sarjubhai Patel、Richard J. Bridges、Charles M. Thompson

  DOI：10.1016/j.bmcl.2009.10.020

  日期：2010.4

  A panel of amino acid analogs and conformationally-restricted amino acids bearing a sulfonic acid were synthesized and tested for their ability to preferentially inhibit the obligate cysteine-glutamate transporter system x(c)(-) versus the vesicular glutamate transporter (VGLUT). Several promising candidate molecules were identified: R/S-4-[4'-carboxyphenyl]-phenylglycine, a biphenyl substituted analog of 4-carboxyphenylglycine and 2-thiopheneglycine-5-sulfonic acid both of which reduced glutamate uptake at system x(c)(-) by 70-75% while having modest to no effect on glutamate uptake at VGLUT. (C) 2009 Elsevier Ltd. All rights reserved.