(-)-3-epinegamycin | 103420-24-2

• 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: (-)-3-epinegamycin
• 英文别名: 2-[[[(3S,5R)-3,6-diamino-5-hydroxyhexanoyl]amino]-methylamino]acetic acid
• CAS: 103420-24-2
• 化学式: C₉H₂₀N₄O₄
• 分子量: 248.282
• InChiKey: IKHFJPZQZVMLRH-NKWVEPMBSA-N

物化性质

• 熔点：
  145-168 °C (decomp)
• 密度：
  1.303±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -5.1
• 重原子数：
  17
• 可旋转键数：
  8
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  142
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (3S,5R)-methyl>isoxazolidin-3-yl>acetic acid 在 palladium on activated charcoal 甲醇 、 氢气 、 溶剂黄146 、 三乙胺 作用下， 以 甲苯 为溶剂， 反应 24.42h， 生成 (-)-3-epinegamycin
  参考文献：
  名称：

  Enantioselective total synthesis of (+)-negamycin and (-)-epinegamycin by an asymmetric 1,3-dipolar cycloaddition

  摘要：

  DOI：

  10.1021/ja00275a064

文献信息

• Asymmetric syntheses of (+)-negamycin, (+)-3-epi-negamycin and sperabillin C via lithium amide conjugate addition
  作者：Stephen G. Davies、Osamu Ichihara、Paul M. Roberts、James E. Thomson

  DOI：10.1016/j.tet.2010.10.067

  日期：2011.1

  and enantioselective reduction of ethyl 4-chloroacetoacetate and the diastereoselective conjugate addition of enantiopure lithium N-benzyl-N-(α-methylbenzyl)amide to an α,β-unsaturated ester have been used as the key steps in the total asymmetric syntheses of (+)-negamycin (in 13 steps and 24% overall yield), (+)-3-epi-negamycin (in 13 steps and 10% overall yield) and sperabillin C (in 17 steps and 13%

  4-氯乙酰乙酸乙酯的化学和对映选择性还原以及对映纯N-苄基-N-（α-甲基苄基）酰胺对映体选择性共轭加成到α，β-不饱和酯中已被用作总不对称反应的关键步骤（+）的合成- negamycin（在13个步骤和24％的总收率），（+） - 3-外延-negamycin（在13个步骤和10％的总产率）和sperabillin C（在17个步骤，13％总收率）从可商购的原料中提取。
• Methods for inducing an immune response
  申请人：MOONSHOT PHARMA LLC

  公开号：US11135221B2

  公开（公告）日：2021-10-05

  Provided herein, inter alia, are compositions and methods for generating a immune response in an individual and/or inducing the expression of neoantigens on the surface of abnormal (such as proliferative) cells via promotion of premature termination codon (PTC) read-through and inhibition of nonsense-mediated decay (NMD) of messenger RNAs (mRNAs) bearing PTCs.

  本文特别提供了通过促进过早终止密码子（PTC）读通和抑制带有 PTC 的信使核糖核酸（mRNA）的无意义介导衰变（NMD），在个体中产生免疫反应和/或诱导异常（如增殖）细胞表面表达新抗原的组合物和方法。
• Asymmetric total synthesis of (+)-negamycin and (-)-3-epinegamycin via enantioselective 1,3-dipolar cycloaddition
  作者：Katsura Kasahara、Hideo Iida、Chihiro Kibayashi

  DOI：10.1021/jo00270a037

  日期：1989.4
• Negamycin Analogue with Readthrough-Promoting Activity as a Potential Drug Candidate for Duchenne Muscular Dystrophy
  作者：Akihiro Taguchi、Shigenobu Nishiguchi、Masataka Shiozuka、Takao Nomoto、Mayuko Ina、Shouta Nojima、Ryoichi Matsuda、Yoshiaki Nonomura、Yoshiaki Kiso、Yuri Yamazaki、Fumika Yakushiji、Yoshio Hayashi

  DOI：10.1021/ml200245t

  日期：2012.2.9

  A series of (+)-negamycin 1 analogues were synthesized, and their readthrough-promoting activity was evaluated for nonsense mutations in Duchenne muscular dystrophy 3 (DMD). A structure activity relationship study indicated that 11b was the most potent drug 0 candidate. Immunohistochemical analyses suggested that treatment with 11b restored dystrophin expression in mdx mice, a DMD mouse model. Furthermore, lib decreased serum creatine kinase (CK) levels, an indicator of muscle fiber destruction. Most importantly, 11b demonstrated lower toxicity than 1, and thus, it could be a useful candidate for long-term treatment of DMD.
• KASAHARA, KATSURA;IIDA, HIDEO;KIBAYASHI, CHIHIRO, J. ORG. CHEM., 54,(1989) N, C. 2225-2233
  作者：KASAHARA, KATSURA、IIDA, HIDEO、KIBAYASHI, CHIHIRO

  DOI：——

  日期：——