piricyclamide 7005E1 | 1453832-79-5

• 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: piricyclamide 7005E1
• 英文别名: cyc-MSGVDYYNP；cyclo[Asn-Pro-Met-Ser-Gly-Val-Asp-Tyr-Tyr]；2-[(3S,6S,9S,12S,15S,21S,24S,27S)-3-(2-amino-2-oxoethyl)-21-(hydroxymethyl)-6,9-bis[(4-hydroxyphenyl)methyl]-24-(2-methylsulfanylethyl)-2,5,8,11,14,17,20,23,26-nonaoxo-15-propan-2-yl-1,4,7,10,13,16,19,22,25-nonazabicyclo[25.3.0]triacontan-12-yl]acetic acid
• CAS: 1453832-79-5
• 化学式: C₄₆H₆₂N₁₀O₁₅S
• 分子量: 1027.12
• InChiKey: WZWZBUHIQJOSGJ-DWIHLTNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.85
• 重原子数：
  72.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  394.19
• 氢给体数：
  13.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  香叶基焦磷酸铵盐 、 piricyclamide 7005E1 在 1,4-dithio-D,L-threitol 、 geranyltransferase PirF 、 magnesium chloride 作用下， 以 aq. buffer 为溶剂， 反应 30.0h， 生成 、
  参考文献：
  名称：

  Post-Translational Tyrosine Geranylation in Cyanobactin Biosynthesis

  摘要：

  Prenylation is a widespread modification that improves the biological activities of secondary metabolites. This reaction also represents a key modification step in biosyntheses of cyanobactins, a family of ribosomally synthesized and post-translationally modified peptides (RiPPs) produced by cyanobacteria. In cyanobactins, amino acids are commonly isoprenylated by ABBA prenyltransferases that use C-5 donors. Notably, mass spectral analysis of piricyclamides from a fresh-water cyanobacterium suggested that they may instead have a C-10 geranyl group. Here we characterize a novel geranyltransferase involved in piricyclamide biosynthesis. Using the purified enzyme, we show that the enzyme PirF catalyzes Tyr O-geranylation, which is an unprecedented post-translational modification. In addition, the combination of enzymology and analytical chemistry revealed the structure of the final natural product, piricyclamide 7005E1, and the regioselectivity of PirF, which has potential as a synthetic biological tool providing drug like properties to diverse small molecules.

  DOI：

  10.1021/jacs.8b03137