benzyl (2S,3S)-2-amino-4-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxybutanoate | 214604-62-3

• 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: benzyl (2S,3S)-2-amino-4-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxybutanoate
• CAS: 214604-62-3
• 化学式: C₁₆H₁₈N₆O₄
• 分子量: 358.357
• InChiKey: BJRODEPHIHTDKN-QWRGUYRKSA-N

物化性质

• 密度：
  1.619±0.14 g/cm3(Temp: 25 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  158
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl (2S,3S)-2-amino-4-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxybutanoate 在 盐酸 作用下， 以 乙酸乙酯 为溶剂， 生成
  参考文献：
  名称：

  Application of l-threonine aldolase-catalyzed reaction for the preparation of a peptidic mimetic of RNA: A leading compound of Vero-toxin inhibitors

  摘要：

  A peptidic mimetic of RNA having a guanine-adenine-guanine code as a base sequence was prepared as a leading compound of Vero-toxin inhibitors. The synthesized hexapeptide is composed from two gamma-guanyl-beta-hydroxy-alpha-L-amino acids and one gamma-adenyl-beta-hydroxy-alpha-L-amino acid, which were prepared by using L-threonine aldolase-catalyzed reaction, in addition to three glycines. On designing this peptide, the beta-hydroxyl groups in the novel cc-amino acids are compared to the 2'-hydroxyl groups of RNA, and glycine was chosen as the mimic of the phosphate groups in the RNA backbone. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(98)01567-6
• 作为产物：
  描述：

  2-Amino-6-hydroxypurin-9-ylacetaldehyde 在 Candida humicola AKU 4586 L-threonine aldolase 作用下， 以 水 为溶剂， 反应 24.0h， 生成 benzyl (2S,3S)-2-amino-4-(2-amino-6-oxo-1H-purin-9-yl)-3-hydroxybutanoate
  参考文献：
  名称：

  Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases

  摘要：

  基于UDP-N-乙酰葡糖胺的多肽模拟物尼克霉素Z对N-乙酰葡糖胺转移酶具有强效抑制活性的背景，我们设计并合成了新型的GDP-岩藻糖多肽模拟物，其目标是抑制从GDP-岩藻糖转移l-岩藻糖至寡糖的岩藻糖转移酶。GDP-岩藻糖模拟物的合成路线是利用 l-苏氨酸醛缩酶催化的酶促醛缩反应来制备携带δ-²-羟基-δ±-l-氨基酸的鸟嘌呤，这是一种关键的合成中间体。

  DOI：

  10.1055/s-2003-44984

文献信息

• Application of l-threonine aldolase-catalyzed reaction for the preparation of a peptidic mimetic of RNA: A leading compound of Vero-toxin inhibitors
  作者：Tsuyoshi Miura、Masayuki Fujii、Kazushi Shingu、Ikuo Koshimizu、Junko Naganoma、Tetsuya Kajimoto、Yoshiteru Ida

  DOI：10.1016/s0040-4039(98)01567-6

  日期：1998.10

  A peptidic mimetic of RNA having a guanine-adenine-guanine code as a base sequence was prepared as a leading compound of Vero-toxin inhibitors. The synthesized hexapeptide is composed from two gamma-guanyl-beta-hydroxy-alpha-L-amino acids and one gamma-adenyl-beta-hydroxy-alpha-L-amino acid, which were prepared by using L-threonine aldolase-catalyzed reaction, in addition to three glycines. On designing this peptide, the beta-hydroxyl groups in the novel cc-amino acids are compared to the 2'-hydroxyl groups of RNA, and glycine was chosen as the mimic of the phosphate groups in the RNA backbone. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Design and Synthesis of Peptide Mimetics of GDP-Fucose: Targeting Inhibitors of Fucosyltransferases
  作者：Tetsuya Kajimoto、Toru Tanaka、Chihiro Tsuda、Tsuyoshi Miura、Toshiyuki Inazu、Shuichi Tsuji、Shoko Nishihara、Mitsuko Hisamatsu

  DOI：10.1055/s-2003-44984

  日期：——

  Novel peptide mimetics of GDP-fucose were designed and synthesized targeting inhibitors of the fucosyltransferases that transfer l-fucose from GDP-fucose to oligosaccharides, on the basis of the background that nikkomycin Z, a peptide mimetic of UDP-N-acetylglucosamine, shows potent inhibitory activity toward an N-acetylglucosamine transfer enzyme. The synthetic routes of the GDP-fucose mimetics take advantage of an enzymatic aldol reaction catalyzed by l-threonine aldolase to prepare the guanine carrying β-hydroxy-α-l-amino acid, a key synthetic intermediate.

  基于UDP-N-乙酰葡糖胺的多肽模拟物尼克霉素Z对N-乙酰葡糖胺转移酶具有强效抑制活性的背景，我们设计并合成了新型的GDP-岩藻糖多肽模拟物，其目标是抑制从GDP-岩藻糖转移l-岩藻糖至寡糖的岩藻糖转移酶。GDP-岩藻糖模拟物的合成路线是利用 l-苏氨酸醛缩酶催化的酶促醛缩反应来制备携带δ-²-羟基-δ±-l-氨基酸的鸟嘌呤，这是一种关键的合成中间体。