(R)-Met-O-iPr⁺ (Cl^-) | 343962-70-9

• 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: (R)-Met-O-iPr⁺ (Cl^-)
• 英文别名: D-methionine isopropyl ester; hydrochloride；D-Methionin-isopropylester; Hydrochlorid；propan-2-yl (2R)-2-amino-4-methylsulfanylbutanoate;hydrochloride
• CAS: 343962-70-9
• 化学式: C₈H₁₇NO₂S*ClH
• 分子量: 227.755
• InChiKey: ONXXRAMAPIOLSS-OGFXRTJISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.44
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  77.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-Met-O-iPr⁺ (Cl^-) 在 叔丁基氯化镁 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 8.83h， 生成 propan-2-yl (2R)-2-[[[(2R,3R,4S,5R)-5-(2,4-dioxopyrimidin-1-yl)-4-fluoro-3-hydroxy-4-methyloxolan-2-yl]methoxy-phenoxyphosphoryl]amino]-4-methylsulfanylbutanoate
  参考文献：
  名称：

  Discovery of 2′-α-C-Methyl-2′-β-C-fluorouridine Phosphoramidate Prodrugs as Inhibitors of Hepatitis C Virus

  摘要：

  2'-alpha-C-Methyl-2'-beta-C-fluorouridine and its phosphoramidate prodrugs were synthesized and evaluated for their inhibitory activity against HCV. The structure-activity relationship analysis of the phosphoramidate moiety found that 17m, 17q, and 17r exhibit potent activities against HCV, with EC50 values of 1.82 +/- 0.19, 0.88 +/- 0.12, and 2.24 +/- 0.22 mu M, respectively. The docking study revealed that the recognition of the 2'-beta-F by Arg158, 3'-OH by N291, and the Watson Crick pairing with the template allowed 23 to form the in-line conformation necessary for its incorporation into the viral RNA chain.

  DOI：

  10.1021/acsmedchemlett.6b00270
• 作为产物：
  描述：

  D-蛋氨酸 、 异丙醇 在 盐酸 作用下， 生成 (R)-Met-O-iPr⁺ (Cl^-)
  参考文献：
  名称：

  高甲基化葡萄糖寡糖对氨基酸酯盐的手性鉴别

  摘要：

  使用FAB质谱法评估了全甲基化的吡喃葡萄糖寡糖对氨基酸2-丙基酯盐酸盐的手性鉴别能力。在给定的全甲基同型寡糖，全甲基β-纤维寡糖系列（II）显示出显着高的小号朝向色氨酸酯盐-选择性（TRP-O-我镨+）独立的数字（的Ñ吡喃葡萄糖单元的）（Ñ = 2–5）。全甲基化的β-麦芽低聚糖系列（I）的六聚体和七聚体显示出与全甲基化的α-和β-环糊精非常相似的对映选择性。

  DOI：

  10.1016/s0040-4020(01)00390-8

文献信息

• Evaluation of Chiral Amino Acid Discrimination by a Permethylated Cyclic Tetrasaccharide,<i>cyclo</i>-{→6)-α-D-Glc<i>p</i>-(1→3)-α-D-Glc<i>p</i>-(1→6)-α-D-Glc<i>p</i>-(1→3)-α-D-Glc<i>p</i>-(1→}, Using FAB Mass Spectrometry
  作者：Motohiro Shizuma、Taro Kiso、Hisashi Terauchi、Yoshio Takai、Hitoshi Yamada、Tomoyuki Nishimoto、Daisuke Ono、Osamu Shimomura、Ryoki Nomura、Yoshikatsu Miwa、Masaki Nakamura、Hirofumi Nakano

  DOI：10.1246/cl.2008.1054

  日期：2008.10.5

  The novel cyclic oligosaccharide, permethylated tetrasaccharide (CTS), determinates the enantiomers of chiral amino acid isopropyl ester hydrochlorides.

  新型环状寡糖，完全甲基化的四糖（CTS），决定了手性氨基酸异丙基酯盐酸盐的对映体。
• Chiral discrimination of permethylated gluco-oligosaccharide toward amino acid ester salts
  作者：Motohiro Shizuma、Hiroshi Adachi、Akinori Amemura、Yoshio Takai、Tokuji Takeda、Masami Sawada

  DOI：10.1016/s0040-4020(01)00390-8

  日期：2001.5

  The chiral discrimination ability of permethylated glucopyrano-oligosaccharides toward amino acid 2-propyl ester hydrochlorides was evaluated using FAB mass spectrometry. In the given permethylated homo-oligosaccharides, permethylated β-cello-oligosaccharide series (II) showed remarkably higher S-selectivity toward tryptophan ester salts (Trp-O-iPr+) independent of the numbers (n) of the glucopyranose

  使用FAB质谱法评估了全甲基化的吡喃葡萄糖寡糖对氨基酸2-丙基酯盐酸盐的手性鉴别能力。在给定的全甲基同型寡糖，全甲基β-纤维寡糖系列（II）显示出显着高的小号朝向色氨酸酯盐-选择性（TRP-O-我镨+）独立的数字（的Ñ吡喃葡萄糖单元的）（Ñ = 2–5）。全甲基化的β-麦芽低聚糖系列（I）的六聚体和七聚体显示出与全甲基化的α-和β-环糊精非常相似的对映选择性。
• Discovery of 2′-α-C-Methyl-2′-β-C-fluorouridine Phosphoramidate Prodrugs as Inhibitors of Hepatitis C Virus
  作者：Debin Zeng、Rui Zhang、Quandeng Nie、Lin Cao、Luqing Shang、Zheng Yin

  DOI：10.1021/acsmedchemlett.6b00270

  日期：2016.12.8

  2'-alpha-C-Methyl-2'-beta-C-fluorouridine and its phosphoramidate prodrugs were synthesized and evaluated for their inhibitory activity against HCV. The structure-activity relationship analysis of the phosphoramidate moiety found that 17m, 17q, and 17r exhibit potent activities against HCV, with EC50 values of 1.82 +/- 0.19, 0.88 +/- 0.12, and 2.24 +/- 0.22 mu M, respectively. The docking study revealed that the recognition of the 2'-beta-F by Arg158, 3'-OH by N291, and the Watson Crick pairing with the template allowed 23 to form the in-line conformation necessary for its incorporation into the viral RNA chain.