[U-¹³C,U-¹⁵N]-L-tryptophan | 202406-50-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: [U-¹³C,U-¹⁵N]-L-tryptophan
• 英文别名: (13)C,(15)N-Trp；L-Tryptophan-13C11,15N2；(2S)-2-(15N)azanyl-3-(1H-indol-3-yl)(1,2,3-13C3)propanoic acid
• CAS: 202406-50-6
• 化学式: C₁₁H₁₂N₂O₂
• 分子量: 217.094
• InChiKey: QIVBCDIJIAJPQS-ODOYFPBQSA-N

物化性质

• 熔点：
  280-285 °C (dec.) (lit.)
• 溶解度：
  可溶于酸水溶液（轻微）、水（轻微、加热、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  79.1
• 氢给体数：
  3
• 氢受体数：
  3

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  [U-¹³C,U-¹⁵N]-L-tryptophan 、 9-芴甲基-N-琥珀酰亚胺基碳酸酯 在 碳酸氢钠 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以86%的产率得到Fmoc-L-Trp(13C11,15N2)-OH
  参考文献：
  名称：

  Charting an Unexplored Streptococcal Biosynthetic Landscape Reveals a Unique Peptide Cyclization Motif

  摘要：

  Peptide natural products are often used as signals or antibiotics and contain unusual structural modifications, thus providing opportunities for expanding our understanding of Nature's therapeutic and biosynthetic repertoires. Herein, we have investigated the under-explored biosynthetic potential of Streptococci, prevalent bacteria in mammalian microbiomes that include mutualistic, commensal, and pathogenic members. Using a new bioinformatic search strategy, in which we linked the versatile radical Sadenosylmethionine (RaS) enzyme superfamily to an emerging class of natural products in the context of quorum sensing control, we identified numerous, uncharted biosynthetic loci. Focusing on one such locus, we identified an unprecedented post-translational modification, consisting of a tetrahydro[5,6]benzindole cyclization motif in which four unactivated positions are linked by two C-C bonds in a regio- and stereospecific manner by a single RaS enzyme. Our results expand the scope of reactions that microbes have at their disposal in concocting complex ribosomal peptides.

  DOI：

  10.1021/jacs.8b10266

文献信息

• US9673030B2
  申请人：——

  公开号：US9673030B2

  公开（公告）日：2017-06-06