FR901469 hydrochloride

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 肽模拟物
• 英文名称: FR901469 hydrochloride
• 英文别名: FR901469；3-[(3S,6R,9S,11R,15S,18S,21R,24R,28R,31S,34R,40S,43S,44S)-40-[(1R)-3-amino-1-hydroxy-3-oxopropyl]-11,44-dihydroxy-3,6,24,34-tetrakis[(1R)-1-hydroxyethyl]-18-[(4-hydroxyphenyl)methyl]-21-methyl-2,5,8,14,17,20,23,26,30,33,36,39,42-tridecaoxo-15-propan-2-yl-28-tridecyl-29-oxa-1,4,7,13,16,19,22,25,32,35,38,41-dodecazatricyclo[41.3.0.09,13]hexatetracontan-31-yl]propylazanium;chloride
• 化学式: C₇₁H₁₁₆N₁₄O₂₃*ClH
• 分子量: 1570.24
• InChiKey: VZZJOONOWFZKHA-PVFJZINBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.05
• 重原子数：
  109
• 可旋转键数：
  25
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.72
• 拓扑面积：
  589
• 氢给体数：
  21
• 氢受体数：
  24

反应信息

• 作为反应物：
  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

• FR901469, a Novel Antifungal Antibiotic from an Unidentified Fungus No. 11243. III. Structure Determination.
  作者：AKIHIKO FUJIE、HIDEYUKI MURAMATSU、SEIJI YOSHIMURA、MICHIZANE HASHIMOTO、NOBUHARU SHIGEMATSU、SHIGEHIRO TAKASE

  DOI：10.7164/antibiotics.54.588

  日期：——

  A novel antifungal antibiotic, FR901469, was isolated from an unidentified fungus No. 11243. It is a water-soluble 40-membered macrocyclic lipopeptidolactone, consisting of D-Ala, L-Tyr, L-Val, trans-4OH-L-Pro, trans-3OH-L-Pro, threo-3OH-L-Gln, Gly, L-Orn, L-Thr, three residues of D-alloThr and a (3R)-hydroxypalmitic acid. Its structure, including absolute configurations, was unequivocally determined

  从未知的真菌编号11243中分离出一种新型的抗真菌抗生素FR901469。它是一种水溶性40元大环脂肽内酯，由D-Ala，L-Tyr，L-Val，trans-4OH-L-Pro组成，反式-3OH-L-Pro，苏式-3OH-L-Gln，Gly，L-Orn，L-Thr，D-alloThr的三个残基和（3R）-羟基棕榈酸。根据化学和光谱学证据，其结构（包括绝对构型）明确确定为1。
• Synthesis and biological activity of novel macrocyclic antifungals
  作者：David Barrett、Akira Tanaka、Keiko Harada、Etsuko Watabe、Katsuyuki Maki、Fumiaki Ikeda

  DOI：10.1016/s0960-894x(01)00317-1

  日期：2001.7

  A series of tyrosine-modified derivatives of the macrocyclic lipopeptidolactone FR901469 have been prepared and evaluated for in vitro and in vivo antifungal activity and for hemolytic activity towards red blood cells. Compound 14 displayed significantly reduced hemolytic potential at 1 mg/mL and a comparable protective effect to FR901469 in a mouse candidiasis model. (C) 2001 Elsevier Science Ltd. All rights reserved.
• 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.