(2R,3R)-2-[[2-[[(2S,3R)-5-amino-2-[[(2S,3S)-1-[(2S,3R)-2-[[(2R,3R)-2-[[(2S,4R)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R,3R)-2-amino-3-hydroxybutanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxy-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoic acid | 289614-86-4

• 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,3R)-2-[[2-[[(2S,3R)-5-amino-2-[[(2S,3S)-1-[(2S,3R)-2-[[(2R,3R)-2-[[(2S,4R)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R,3R)-2-amino-3-hydroxybutanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxy-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoic acid
• CAS: 289614-86-4
• 化学式: C₅₀H₇₈N₁₂O₂₁
• 分子量: 1183.24
• InChiKey: CCMLLNSZVVJKMQ-YNFYWAIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -9.1
• 重原子数：
  83
• 可旋转键数：
  29
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  542
• 氢给体数：
  19
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  (2R,3R)-2-[[2-[[(2S,3R)-5-amino-2-[[(2S,3S)-1-[(2S,3R)-2-[[(2R,3R)-2-[[(2S,4R)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R,3R)-2-amino-3-hydroxybutanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxy-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoic acid 、 1-O-[(3R)-1-(benzotriazol-1-yloxy)-1-oxohexadecan-3-yl] 5-O-tert-butyl (2S)-2-(phenylmethoxycarbonylamino)pentanedioate 生成
  参考文献：
  名称：

  Site-specific Structural Transformation of the Novel Antifungal Cycle Depsipeptide FR901469. Synthesis and Biological Activity of FR203903.

  摘要：

  DOI：

  10.7164/antibiotics.54.193
• 作为产物：
  描述：

  FR901469 hydrochloride 在 Actinoplanes utahensis IFO-13244 作用下， 以 phosphate buffer 为溶剂， 以35%的产率得到(2R,3R)-2-[[2-[[(2S,3R)-5-amino-2-[[(2S,3S)-1-[(2S,3R)-2-[[(2R,3R)-2-[[(2S,4R)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R,3R)-2-amino-3-hydroxybutanoyl]amino]propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]-4-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxybutanoyl]amino]-3-hydroxybutanoyl]-3-hydroxypyrrolidine-2-carbonyl]amino]-3-hydroxy-5-oxopentanoyl]amino]acetyl]amino]-3-hydroxybutanoic acid
  参考文献：
  名称：

  An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469

  摘要：

  An expedient synthesis of the lactam analog (2) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 (1), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3, and efficient formation of the 40-membered ring by macrolactamization under high-dilution conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)02047-5

文献信息

• Site-specific Structural Transformation of the Novel Antifungal Cycle Depsipeptide FR901469. Synthesis and Biological Activity of FR203903.
  作者：AKIRA TANAKA、DAVID BARRETT、AKIHIKO FUJIE、NOBUHARU SHIGEMATSU、MICHIZANE HASHIMOTO、SEIJI HASHIMOTO、FUMIAKI IKEDA

  DOI：10.7164/antibiotics.54.193

  日期：——
• An expedient synthesis of the amide analog of the potent antifungal lipopeptidolactone FR901469
  作者：David Barrett、Akira Tanaka、Akihiko Fujie、Nobuharu Shigematsu、Michizane Hashimoto、Seiji Hashimoto

  DOI：10.1016/s0040-4039(00)02047-5

  日期：2001.1

  An expedient synthesis of the lactam analog (2) of the 40-membered lipopeptidolactone antifungal antibiotic, FR901469 (1), is described. The key steps in this synthesis are a novel biotransformation of the natural product to produce the highly versatile linear peptide building block 3, and efficient formation of the 40-membered ring by macrolactamization under high-dilution conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.