乐菌素 | 37294-30-7

• 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
• 中文名称: 乐菌素
• 英文名称: gratisin
• 英文别名: cyclo(-Val1,1'-Orn2,2'-Leu3,3'-D-Phe4,4'-Pro5,5'-D-Tyr6,6'-)2；cyclo(-Val-Orn-Leu-D-Phe-Pro-D-Tyr-)2；GR；(3R,6S,9S,12S,15R,18S,24R,27S,30S,33S,36R,39S)-9,30-bis(3-aminopropyl)-3,24-dibenzyl-15,36-bis[(4-hydroxyphenyl)methyl]-6,27-bis(2-methylpropyl)-12,33-di(propan-2-yl)-1,4,7,10,13,16,22,25,28,31,34,37-dodecazatricyclo[37.3.0.018,22]dotetracontane-2,5,8,11,14,17,23,26,29,32,35,38-dodecone
• CAS: 37294-30-7
• 化学式: C₇₈H₁₁₀N₁₄O₁₄
• 分子量: 1467.82
• InChiKey: KIUGLYLJMHCDMF-AHAYUKIASA-N

物化性质

• 熔点：
  274-276 °C (decomp)
• 沸点：
  1647.3±65.0 °C(Predicted)
• 密度：
  1.29±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.6
• 重原子数：
  106
• 可旋转键数：
  20
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  424
• 氢给体数：
  14
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  H-D-Phe-Pro-D-Tyr-Val-Orn-Leu-ONSu*TFA 在 吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 乐菌素 、 cyclo(-D-Phe-Pro-D-Tyr-Val-Orn-Leu-)
  参考文献：
  名称：

  Biomimetic synthesis of a peptide antibiotic, gratisin

  摘要：

  Recently, we reported the direct formation of a peptide antibiotic, gramicidin S (GS), cyclo(-D-Phe-Pro-Val-Orn-Leu-)2, by the dimerization–cyclization of pentapeptide active esters, D-Phe-Pro-Val-Orn-Leu-ONSu (-ONSu: succinimide ester), having the sequence identical with that of the linear precursor pentapeptide in the biosynthesis of GS and no protecting group on the side-chain of the Orn residue. This biomimetic approach has been extended to the synthesis of a peptide antibiotic, gratisin (GR), cyclo(-D-Phe-Pro-D-Tyr-Val-Orn-Leu-)2, isolated from Bacillus brevis Y-33. In the cyclization of six hexapeptide succinimide esters having a Val, Orn, Leu, D-Phe, Pro or D-Tyr residue at each C-terminus, only H-D-Phe-Pro-D-Tyr-Val-Orn-Leu-ONSu gave semi-GR and GR in yields of 31 and 8%, respectively. Other hexapeptide esters did not give semi-GR and GR. In both biomimetic syntheses of GS and GR, the amino acid sequences having a Leu residue at the C-terminus are essential. In addition, a change in the concentration of peptide and the polarity of reaction solvents influenced greatly the yields of cyclic monomer (semi-GR) and cyclic dimer (GR). However, the yield of GR by dimerization–cyclization of hexapeptide active ester was lower when compared with the direct formation of GS (38%). The difference may result from differences in the chain length and the configurations of amino acid residues around the Pro residue.

  DOI：

  10.1039/a701537b