(S)-2-acetylamino-4-[(R)-1-(ethoxycarbonylmethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-butyric acid ethyl ester | 210281-87-1

• 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: (S)-2-acetylamino-4-[(R)-1-(ethoxycarbonylmethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-butyric acid ethyl ester
• 英文别名: N-acetyl glutathione diethyl ester；aggrelyte-1C；N-acetyl-α-glutamyl ethyl ester-cysteinyl-glycine ethyl ester；Ac-gGlu(OEt)-Cys-Gly-OEt；ethyl (2S)-2-acetamido-5-[[(2R)-1-[(2-ethoxy-2-oxoethyl)amino]-1-oxo-3-sulfanylpropan-2-yl]amino]-5-oxopentanoate
• CAS: 210281-87-1
• 化学式: C₁₆H₂₇N₃O₇S
• 分子量: 405.472
• InChiKey: ZHCZTCXSHJUGQD-RYUDHWBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  141
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  氯(三甲基膦)金 、 (S)-2-acetylamino-4-[(R)-1-(ethoxycarbonylmethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-butyric acid ethyl ester 在 potassium carbonate 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 以58%的产率得到
  参考文献：
  名称：

  [EN] THIOL PHOSPHINE GOLD COMPLEXES FOR USE IN TREATING BACTERIAL INFECTIONS
  [FR] COMPOSÉS ANTIBACTÉRIENS

  摘要：

  公开号：

  WO2017093543A3
• 作为产物：
  描述：

  (4S,9R,14R,19S)-ethyl 19-acetamido-9,14-bis((2-ethoxy-2-oxoethyl)carbamoyl)-4-(ethoxycarbonyl)-2,7,16-trioxo-11,12-dithia-3,8,15-triazaicosan-20-oate 在 水 、 三(2-羰基乙基)磷盐酸盐 作用下， 以 甲醇 为溶剂， 以100%的产率得到(S)-2-acetylamino-4-[(R)-1-(ethoxycarbonylmethyl-carbamoyl)-2-mercapto-ethylcarbamoyl]-butyric acid ethyl ester
  参考文献：
  名称：

  [EN] THIOL PHOSPHINE GOLD COMPLEXES FOR USE IN TREATING BACTERIAL INFECTIONS
  [FR] COMPOSÉS ANTIBACTÉRIENS

  摘要：

  公开号：

  WO2017093543A3

文献信息

• Promotion of Protein Solubility and Reduction in Stiffness in Human Lenses by Aggrelyte-1: Implications for Reversing Presbyopia
  作者：Sudipta Panja、Hanmant Gaikwad、Johanna Rankenberg、Mi-Hyun Nam、Ram H. Nagaraj

  DOI：10.3390/ijms24032196

  日期：——

  With aging, human lenses lose the ability to focus on nearby objects due to decreases in accommodative ability, a condition known as presbyopia. An increase in stiffness or decrease in lens elasticity due to protein aggregation and insolubilization are the primary reasons for presbyopia. In this study, we tested aggrelyte-1 (S,N-diacetyl glutathione diethyl ester) for its ability to promote protein solubility and decrease the stiffness of lenses through its dual property of lysine acetylation and disulfide reduction. Treatment of water-insoluble proteins from aged human lenses (58–75 years) with aggrelyte-1 significantly increased the solubility of those proteins. A control compound that did not contain the S-acetyl group (aggrelyte-1C) was substantially less efficient in solubilizing water-insoluble proteins. Aggrelyte-1-treated solubilized protein had significant amounts of acetyllysine, as measured by Western blotting and LC-MS/MS. Aggrelytes increased the protein-free thiol content in the solubilized protein. Aged mouse (7 months) and human (44–66 years) lenses treated with aggrelyte-1 showed reduced stiffness accompanied by higher free thiol and acetyllysine levels compared with those treated with aggrelyte-1C or untreated controls. Our results suggested that aggrelyte-1 reduced lens stiffness through acetylation followed by disulfide reduction. This proof-of-concept study paves the way for developing aggrelyte-1 and related compounds to reverse presbyopia.

  随着年龄的增长，人类的晶状体会因适应能力下降而失去聚焦附近物体的能力，这种情况被称为老花眼。蛋白质聚集和不溶解导致晶状体硬度增加或弹性降低是老花眼的主要原因。在这项研究中，我们测试了 aggrelyte-1（S,N-二乙酰谷胱甘肽二乙酯）通过赖氨酸乙酰化和二硫化物还原的双重特性促进蛋白质溶解和降低晶状体硬度的能力。用 aggrelyte-1 处理人体老化镜片（58-75 岁）中的水不溶性蛋白质，可显著提高这些蛋白质的溶解度。而不含 S-乙酰基的对照化合物（aggrelyte-1C）在增溶水不溶性蛋白质方面的效率要低得多。通过 Western 印迹和 LC-MS/MS 测定，经 Aggrelyte-1 处理的溶解蛋白质含有大量乙酰赖氨酸。Aggrelytes 增加了溶解蛋白中不含蛋白质的硫醇含量。与使用 aggrelyte-1C 或未使用 aggrelyte-1C 的对照组相比，使用 aggrelyte-1 处理的老龄小鼠（7 个月）和人类（44-66 岁）晶状体的硬度降低，同时游离硫醇和乙酰甘氨酸的含量增加。我们的研究结果表明，aggrelyte-1 通过乙酰化和二硫化物还原作用降低了晶状体的硬度。这项概念验证研究为开发 aggrelyte-1 和相关化合物以逆转老花眼铺平了道路。
• [EN] ANTI-BACTERIAL COMPOUNDS<br/>[FR] COMPOSÉS ANTIBACTÉRIENS
  申请人：AUSPHERIX LTD

  公开号：WO2017093543A2

  公开（公告）日：2017-06-08

  A compound of Formula (II): for use in the prevention or treatment of a bacterial infection.