cyclo-(-D-LAP-D-Ser-D-Tyr-D-Asn-Gly-L-Asn-L-Ser-L-Asn); LAP=N-lauryl-3-amino-3-carbamoylpropanoic acid | 1446714-69-7

• 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
• 英文名称: cyclo-(-D-LAP-D-Ser-D-Tyr-D-Asn-Gly-L-Asn-L-Ser-L-Asn); LAP=N-lauryl-3-amino-3-carbamoylpropanoic acid
• 英文别名: cyclic-NSNG-D-N-D-Y-D-S-D-LAP；(2R,5R,8R,14S,17S,20S,23R)-8,14,20-tris(2-amino-2-oxoethyl)-N-dodecyl-2,17-bis(hydroxymethyl)-5-[(4-hydroxyphenyl)methyl]-3,6,9,12,15,18,21,25-octaoxo-1,4,7,10,13,16,19,22-octazacyclopentacosane-23-carboxamide
• CAS: 1446714-69-7
• 化学式: C₄₅H₇₀N₁₂O₁₅
• 分子量: 1019.12
• InChiKey: MASOKCCEVQELSY-OIBHKJLYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  72
• 可旋转键数：
  22
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  452
• 氢给体数：
  15
• 氢受体数：
  15

反应信息

• 作为产物：
  描述：

  (2R,5R,8R,14S,17S,20S,23R)-N-dodecyl-2,17-bis[(2-methylpropan-2-yl)oxymethyl]-5-[[4-[(2-methylpropan-2-yl)oxy]phenyl]methyl]-3,6,9,12,15,18,21,25-octaoxo-8,14,20-tris[2-oxo-2-(tritylamino)ethyl]-1,4,7,10,13,16,19,22-octazacyclopentacosane-23-carboxamide 在 TIPS 作用下， 以 水 为溶剂， 反应 2.0h， 以57%的产率得到cyclo-(-D-LAP-D-Ser-D-Tyr-D-Asn-Gly-L-Asn-L-Ser-L-Asn); LAP=N-lauryl-3-amino-3-carbamoylpropanoic acid
  参考文献：
  名称：

  环状八-脂肽伯克霍尔定类似物的合成和抗真菌活性

  摘要：

  描述了burkholdines的环状八肽衍生物的合成和抗真菌活性。为了构建环状八肽，在溶液相中使用了Fmoc-SPPS和DIC / HOBt与环化的组合。评估合成肽的抑菌活性，其MIC值为酿酒酵母，米曲霉和粘念珠菌。结果，Bk-1097类似物的脂质侧链和每个氨基酸的立体化学显着影响了抗真菌活性。

  DOI：

  10.1016/j.bmcl.2013.04.091

文献信息

• Structure activity relationship study of burkholdine analogues toward simple antifungal agents
  作者：Hiroyuki Konno、Kanako Abumi、Yasuhiro Sasaki、Shigekazu Yano、Kazuto Nosaka

  DOI：10.1016/j.bmcl.2015.05.088

  日期：2015.8

  Cyclic and linear lipopeptides, burkholdine analogues, were synthesized by conventional Fmoc-SPPS and cyclisation with DIPC/HOBt in the solution phase. Synthesized peptides were evaluated for antifungal activities with MIC values against Saccharomyces cerevisiae and Aspergillus oryzae. As a result, the stereochemistry of the amino acid residues and sequences of burkholdine analogues exerted a significant influence on antifungal activities. In addition, we found a linear burkholdine analogue with moderate antifungal activities. (C) 2015 Elsevier Ltd. All rights reserved.
• Synthesis and antifungal activities of cyclic octa-lipopeptide burkholdine analogues
  作者：Hiroyuki Konno、Yusuke Otsuki、Kenta Matsuzaki、Kazuto Nosaka

  DOI：10.1016/j.bmcl.2013.04.091

  日期：2013.7

  Synthesis and antifungal activity of cyclic octapeptide derivatives of burkholdines are described. To construct cyclic octapeptides, the combination of Fmoc-SPPS and cyclization with DIC/HOBt in the solution phase was employed. Synthesized peptides were evaluated for antifungal activity with MIC values against Saccharomyces cerevisiae, Aspergillus oryzae, and Candida viswanathii. As a result, the lipid

  描述了burkholdines的环状八肽衍生物的合成和抗真菌活性。为了构建环状八肽，在溶液相中使用了Fmoc-SPPS和DIC / HOBt与环化的组合。评估合成肽的抑菌活性，其MIC值为酿酒酵母，米曲霉和粘念珠菌。结果，Bk-1097类似物的脂质侧链和每个氨基酸的立体化学显着影响了抗真菌活性。