(2R,3S)-microginin | 161346-20-9

• 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: (2R,3S)-microginin
• 英文别名: microginin；H-bAla(2R-OH,3S-heptyl)-Ala-Val-N(Me)Tyr-Tyr-OH；(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2R,3S)-3-amino-2-hydroxydecanoyl]amino]propanoyl]amino]-3-methylbutanoyl]-methylamino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoic acid
• CAS: 161346-20-9
• 化学式: C₃₇H₅₅N₅O₉
• 分子量: 713.872
• InChiKey: KPCUJSJUCHBAJR-TYOPREAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  232
• 氢给体数：
  8
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (2R,3S)-microginin 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以3.6 mg的产率得到Ahda-Ala-Val
  参考文献：
  名称：

  Microginins, Zinc Metalloproteases Inhibitors from the Cyanobacterium Microcystis aeruginosa

  摘要：

  Eight new linear peptides, microginins 478 (1), 51-A (2), 51-B (3) and 91-A (4) to 91-E (8), congeners of mioroginin, were isolated from the cyanobacterium Microcystis aeruginosa. These structures were elucidated to be 1-8 on the basis of 2D NMR data and chemical degradation. These peptides inhibited aminopeptidase M (1, 2 and 6-8) and angiotensin-converting enzyme (1). Tnt: structure-activity relationship within a series of degradation and derivative products of microginin was investigated by the chemical studies. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00770-5
• 作为产物：
  描述：

  methyl 2S-amino-3-(4-benzyloxyphenyl)propionate hydrochloride 在 钯 盐酸 、 lithium hydroxide 、 氢气 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 、 N,N-二异丙基乙胺 、 焦碳酸二乙酯 作用下， 以 四氢呋喃 、 溶剂黄146 、 N,N-二甲基甲酰胺 为溶剂， 反应 136.0h， 生成 (2R,3S)-microginin
  参考文献：
  名称：

  Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa

  摘要：

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.

  DOI：

  10.1016/s0040-4020(01)89431-x

文献信息

• Total synthesis of microginin, an angiotensin-converting enzyme inhibitory pentapeptide from the blue-green alga Microcystis aeruginosa
  作者：Fumiyoshi Matsuura、Yasumasa Hamada、Takayuki Shioiri

  DOI：10.1016/s0040-4020(01)89431-x

  日期：——

  Microginin, an angiotensin-converting enzyme inhibitory peptide isolated form the blue-green alga Microcystis aeruginosa, and its three diastereoisomers were efficiently synthesized, which unequivocally established the absolute stereostructure of microginin to be 1d.
• Microginins, Zinc Metalloproteases Inhibitors from the Cyanobacterium Microcystis aeruginosa
  作者：Keishi Ishida、Taku Kato、Masahiro Murakami、Masayuki Watanabe、Mariyo F. Watanabe

  DOI：10.1016/s0040-4020(00)00770-5

  日期：2000.10

  Eight new linear peptides, microginins 478 (1), 51-A (2), 51-B (3) and 91-A (4) to 91-E (8), congeners of mioroginin, were isolated from the cyanobacterium Microcystis aeruginosa. These structures were elucidated to be 1-8 on the basis of 2D NMR data and chemical degradation. These peptides inhibited aminopeptidase M (1, 2 and 6-8) and angiotensin-converting enzyme (1). Tnt: structure-activity relationship within a series of degradation and derivative products of microginin was investigated by the chemical studies. (C) 2000 Elsevier Science Ltd. All rights reserved.