methanesulfonyl-glutamic acid

• 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: methanesulfonyl-glutamic acid
• 英文别名: (2S)-2-(methanesulfonamido)pentanedioic acid
• 化学式: C₆H₁₁NO₆S
• 分子量: 225.222
• InChiKey: AUJMVKJHYAABAM-BYPYZUCNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  129
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methanesulfonyl-glutamic acid 在 sodium methylate 、 (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 作用下， 生成 (4S)-4-(methanesulfonamido)-5-[2-(3-methoxy-4-pent-2-ynoxyphenyl)ethylamino]-5-oxopentanoic acid
  参考文献：
  名称：

  N-Sulfonyl Amino Acid Amides, a Novel Class of Compounds with Fungicidal Activity [1]

  摘要：

  已经设计和制备了新型的疫霉菌杀菌剂。这些N-磺酰氨基酸酰胺的合成方法已经概述。生物测定表明它们对重要植物病害如晚疫病菌（番茄和马铃薯晚疫病）和葡萄霜霉病（葡萄霜霉病）具有很高的效力。结构活性关系研究也已讨论。

  DOI：

  10.2533/000942903777678542
• 作为产物：
  描述：

  L-谷氨酸二叔丁酯盐酸盐 在 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 methanesulfonyl-glutamic acid
  参考文献：
  名称：

  N-Substituted Glutamyl Sulfonamides as Inhibitors of Glutamate Carboxypeptidase II (GCP2)

  摘要：

  Glutamate carboxypeptidase II (GCP2) is a membrane‐bound cell‐surface peptidase which is implicated in several neurological disorders and is also over‐expressed in prostate tumor cells. There is a significant interest in the inhibition of GCP2 as a means of neuroprotection, while GCP2 inhibition as a method to treat prostate cancer remains a topic of further investigation. The key zinc‐binding functional group of the well‐characterized classes of GCP2 inhibitors (phosphonates and phosphoramidates) is tetrahedral and negatively charged at neutral pH, while glutamyl urea class of inhibitors possesses a planar and neutral zinc‐binding group. This study introduces a new class of GCP2 inhibitors, N‐substituted glutamyl sulfonamides, which possess a neutral tetrahedral zinc‐binding motif. A library containing 15 secondary sulfonamides and 4 tertiary (N‐methyl) sulfonamides was prepared and evaluated for inhibitory potency against purified GCP2 enzyme activity. While most inhibitors lacked potency at 100 μm, short alkyl sulfonamides exhibited promising low micromolar potency, with the optimal inhibitor in this series being glutamyl N‐(propylsulfonamide) (2g). Lastly, molecular docking was used to develop a model to formulate an explanation for the relative inhibitory potencies employed for this class of inhibitors.

  DOI：

  10.1111/j.1747-0285.2011.01085.x

文献信息

• PROCESS FOR PREPARING OPTICALLY ACTIVE 2-PIPERAZINECARBOXYLIC ACID DERIVATIVES
  申请人：TORAY INDUSTRIES, INC.

  公开号：EP0906906A1

  公开（公告）日：1999-04-07

  Optically-active 2-piperazinecarboxylic acid derivatives are produced through diastereomer salt resolution using optically-active acidic amino acid derivative as the resolving reagent. In this method, the recovery of the resolving reagent used is high, and the production efficiency to produce the optically-active products is high. As the optically-active acidic amino acid derivatives, usable are optically-active, N-acylated acidic amino acid derivatives and optically-active, N-sulfonylated acidic amino acid derivatives.

  使用具有光学活性的酸性氨基酸衍生物作为解析试剂，通过非对映异构盐解析法生产出具有光学活性的 2-哌嗪甲酸衍生物。在这种方法中，所用的解析试剂回收率高，生产光学活性产品的效率也高。 光学活性酸性氨基酸衍生物包括光学活性 N-酰化酸性氨基酸衍生物和光学活性 N-磺酰化酸性氨基酸衍生物。
• PARAKERATOSIS INHIBITOR AND EXTERNAL COMPOSITION FOR SKIN
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP1688126A1

  公开（公告）日：2006-08-09

  To provide a parakeratosis inhibitor, pore reducing agent and skin roughness preventing/ameliorating agent that exhibit capabilities of parakeratosis inhibition, pore reduction, skin roughness prevention/amelioration, etc., and further provide a skin preparation for external use having these capabilities. There are provide a parakeratosis inhibitor and a pore reducing agent each comprising at least one compound selected from the group consisting of a glycine derivative, an aminodicarboxylic acid derivative, an acylaminodicarboxylic acid derivative, a pyrrolidinecarboxylic acid derivative, a piperidinecarboxylic acid derivative, a hexamethyleneiminecarboxylic acid, a beta-alanine derivative and salts of these derivatives. Further, there are provided a parakeratosis inhibitor, a pore reducing agent and a skin roughness preventing/ameliorating agent each comprising at least one compound selected from the group consisting of specified glycine derivatives and salts thereof and specified aminosulfuric acid derivatives and salts thereof. Still further, there are provided skin preparations for external use comprising these compounds.

  提供一种具有抑制角化病、缩小毛孔、防止/改善皮肤粗糙等功能的角化病抑制剂、毛孔缩小剂和皮肤粗糙防止/改善剂，并进一步提供一种具有这些功能的外用皮肤制剂。本发明提供了一种角化抑制剂和一种毛孔缩小剂，它们都包含至少一种选自以下组别的化合物：甘氨酸衍生物、氨基二羧酸衍生物、酰氨基二羧酸衍生物、吡咯烷羧酸衍生物、哌啶羧酸衍生物、六亚甲基亚氨基羧酸、β-丙氨酸衍生物和这些衍生物的盐。此外，还提供了一种角化抑制剂、一种毛孔缩小剂和一种防止/改善皮肤粗糙剂，每一种都包含至少一种选自特定甘氨酸衍生物及其盐类和特定氨基硫酸衍生物及其盐类的化合物。此外，还提供了包含这些化合物的外用皮肤制剂。
• Parakeratosis inhibitor and skin preparation for external use
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP2491980A2

  公开（公告）日：2012-08-29

  To provide a parakeratosis inhibitor agent or a pore-shrinking agent comprising one or two or more compounds selected from a group consisting of benzoylaminodicarboxylic acid derivatives or benzenesulfonylaminodicarboxylic acid derivatives, as well as the salts of said derivatives as represented by general formula (2) (2) and a skin preparation for inhibiting parakeratosis for external use comprising a parakeratosis inhibitor agent and a skin preparation for shrinking pores for external use comprising a pore-shrinking agent.

  提供一种角化病抑制剂或毛孔收缩剂，其包含一种或两种或两种以上选自苯甲酰氨基二羧酸衍生物或苯磺酰氨基二羧酸衍生物以及通式(2)代表的上述衍生物的盐类的化合物。 (2) 和一种抑制角化病的外用皮肤制剂，包括一种角化病抑制剂和一种收缩毛孔的外用皮肤制剂，包括一种收缩毛孔剂。
• Parakeratosis inhibitor and external composition for skin
  申请人：SHISEIDO COMPANY LIMITED

  公开号：EP2491981A2

  公开（公告）日：2012-08-29

  To provide a parakeratosis inhibitor agent, pore-shrinking agent, or skin roughness preventing/ameliorating agent comprising one or two or more compounds selected from a group consisting of aminosulfuric acid derivatives and the salts thereof as represented by general formula (10) (10), a skin preparation for inhibiting parakeratosis for external use comprising a parakeratosis inhibitor agent, a skin preparation for shrinking pores for external use comprising a pore-shrinking agent and a skin preparation for preventing/ameliorating skin roughness for external use comprising a skin roughness preventing/ameliorating agent.

  提供一种角化抑制剂、毛孔收缩剂或皮肤粗糙预防/改善剂，其包含一种或两种或两种以上选自氨基硫酸衍生物及其盐组成的组的化合物，如通式（10）所示 (10)，一种外用的抑制角化病的皮肤制剂，包括角化病抑制剂；一种外用的收缩毛孔的皮肤制剂，包括毛孔收缩剂；一种外用的防止/改善皮肤粗糙的皮肤制剂，包括防止/改善皮肤粗糙剂。
• Parakeratosis Inhibitor and Skin Preparation for External use
  申请人：Kaminuma Mikiko

  公开号：US20070225380A1

  公开（公告）日：2007-09-27

  To provide a parakeratosis inhibitor, pore reducing agent and skin roughness preventing/ameliorating agent that exhibit capabilities of parakeratosis inhibition, pore reduction, skin roughness prevention/amelioration, etc., and further provide a skin preparation for external use having these capabilities. There are provide a parakeratosis inhibitor and a pore reducing agent each comprising at least one compound selected from the group consisting of a glycine derivative, an aminodicarboxylic acid derivative, an acylaminodicarboxylic acid derivative, a pyrrolidinecarboxylic acid derivative, a piperidinecarboxylic acid derivative, a hexamethyleneiminecarboxylic acid, a beta-alanine derivative and salts of these derivatives. Further, there are provided a parakeratosis inhibitor, a pore reducing agent and a skin roughness preventing/ameliorating agent each comprising at least one compound selected from the group consisting of specified glycine derivatives and salts thereof and specified aminosulfuric acid derivatives and salts thereof. Still further, there are provided skin preparations for external use comprising these compounds.