cyclo[L-Val-L-Ser-L-Ile-L-Asn-L-Val-L-Phe-L-Pro-]

• 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[L-Val-L-Ser-L-Ile-L-Asn-L-Val-L-Phe-L-Pro-]
• 英文别名: Microseiramide；2-[(3S,6S,9S,12S,15S,18S,21S)-18-benzyl-9-[(2S)-butan-2-yl]-6-(hydroxymethyl)-2,5,8,11,14,17,20-heptaoxo-3,15-di(propan-2-yl)-1,4,7,10,13,16,19-heptazabicyclo[19.3.0]tetracosan-12-yl]acetamide
• 化学式: C₃₇H₅₆N₈O₉
• 分子量: 756.9
• InChiKey: FXQYYQRZKVKMDS-RITHUONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  258
• 氢给体数：
  8
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  cyclo[L-Val-L-Ser-L-Ile-L-Asn-L-Val-L-Phe-L-Pro-] 在 盐酸 、 水 作用下， 反应 20.0h， 生成 L-缬氨酸 、 L-丝氨酸 、 L-异亮氨酸 、 L-天冬酰胺 、 L-苯丙氨酸 、 L-脯氨酸
  参考文献：
  名称：

  Microseiramide from the freshwater cyanobacterium Microseira sp. UIC 10445

  摘要：

  Microseiramide (1), a cyclic heptapeptide, was isolated from a sample of the freshwater cyanobacterium Microseira sp. UIC 10445 collected in a shallow lake in Northern Indiana. Taxonomic identification of UIC 10445 was performed by a combination of morphological and phylogenetic characterization. Phylogenetic analysis revealed that UIC 10445 was a member of the recently described genus Microseira, which is phylogenetically distinct from the morphologically similar genera, Moorea and Lyngbya. The planar structure of microseiramide (1) was determined by extensive 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of amino acid residues were determined using acid hydrolysis followed by the advanced Marfey's analysis. Microseiramide (1) is the first cyclic peptide reported from a Microseira sp., and the structure of microseiramide (1) is distinct from the previously known metabolites from cyanobacteria of the genera Moorea and Lyngbya. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.phytol.2015.05.003

文献信息

• Microseiramide from the freshwater cyanobacterium Microseira sp. UIC 10445
  作者：Shangwen Luo、Aleksej Krunic、George E. Chlipala、Jimmy Orjala

  DOI：10.1016/j.phytol.2015.05.003

  日期：2015.9

  Microseiramide (1), a cyclic heptapeptide, was isolated from a sample of the freshwater cyanobacterium Microseira sp. UIC 10445 collected in a shallow lake in Northern Indiana. Taxonomic identification of UIC 10445 was performed by a combination of morphological and phylogenetic characterization. Phylogenetic analysis revealed that UIC 10445 was a member of the recently described genus Microseira, which is phylogenetically distinct from the morphologically similar genera, Moorea and Lyngbya. The planar structure of microseiramide (1) was determined by extensive 1D and 2D NMR experiments as well as HRESIMS analysis. The absolute configurations of amino acid residues were determined using acid hydrolysis followed by the advanced Marfey's analysis. Microseiramide (1) is the first cyclic peptide reported from a Microseira sp., and the structure of microseiramide (1) is distinct from the previously known metabolites from cyanobacteria of the genera Moorea and Lyngbya. (C) 2015 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.