rhabdoplanin A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: rhabdoplanin A
• 英文别名: Rhabdoplanin A；(2R)-2-[[(2S)-1-[2-[4-[(2S,3R,4S,5R,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxyphenyl]ethenylamino]-3-(1-methylindol-3-yl)-1-oxopropan-2-yl]amino]-3-phenyl-N-(2-phenylethyl)propanamide
• 化学式: C₄₅H₅₁N₅O₇
• 分子量: 773.929
• InChiKey: CZCBGVSDAAGXFI-GYHVRWMKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  57
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  163
• 氢给体数：
  6
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  苯丙酮酸 、 rhabduscin 、 1-甲基-L-色氨酸 、 2-苯乙胺 以 aq. buffer 为溶剂， 反应 48.0h， 生成 rhabdoplanin A 、
  参考文献：
  名称：

  An Ugi-like Biosynthetic Pathway Encodes Bombesin Receptor Subtype-3 Agonists

  摘要：

  Isocyanide functional groups can be found in a variety of natural products. Rhabduscin is one such isocyanide-functionalized immunosuppressant produced in Xenorhabdus and Photorhabdus gammaproteobacterial pathogens, and deletion of its biosynthetic gene cluster inhibits virulence in an invertebrate animal infection model. Here, we characterized the first "opine-glycopeptide" class of natural products termed rhabdoplanins, and strikingly, these molecules are spontaneously produced from rhabduscin via an unprecedented multicomponent "Ugi-like" reaction sequence in nature. The rhabdoplanins also represent new lead G protein-coupled receptor (GPCR) agonists, stimulating the bombesin receptor subtype-3 (BB3) GPCR.

  DOI：

  10.1021/jacs.9b04183

文献信息

• An Ugi-like Biosynthetic Pathway Encodes Bombesin Receptor Subtype-3 Agonists
  作者：Joonseok Oh、Nam Y. Kim、Haiwei Chen、Noah W. Palm、Jason M. Crawford

  DOI：10.1021/jacs.9b04183

  日期：2019.10.16

  Isocyanide functional groups can be found in a variety of natural products. Rhabduscin is one such isocyanide-functionalized immunosuppressant produced in Xenorhabdus and Photorhabdus gammaproteobacterial pathogens, and deletion of its biosynthetic gene cluster inhibits virulence in an invertebrate animal infection model. Here, we characterized the first "opine-glycopeptide" class of natural products termed rhabdoplanins, and strikingly, these molecules are spontaneously produced from rhabduscin via an unprecedented multicomponent "Ugi-like" reaction sequence in nature. The rhabdoplanins also represent new lead G protein-coupled receptor (GPCR) agonists, stimulating the bombesin receptor subtype-3 (BB3) GPCR.