surugamides C | 1444002-14-5

• 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: surugamides C
• 英文别名: surugamide E；cyclo[-L-Ile-D-Ile-L-Lys-L-Val-D-Phe-D-Leu-L-Ile-D-Ala-]；Surugamide C；(3S,6R,9S,12R,15S,18R,21R,24S)-3-(4-aminobutyl)-21-benzyl-9,15-bis[(2S)-butan-2-yl]-6-[(2R)-butan-2-yl]-12-methyl-18-(2-methylpropyl)-24-propan-2-yl-1,4,7,10,13,16,19,22-octazacyclotetracosane-2,5,8,11,14,17,20,23-octone
• CAS: 1444002-14-5
• 化学式: C₄₇H₇₉N₉O₈
• 分子量: 898.2
• InChiKey: CBNRHESAARZEOI-VIKOQBBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.6
• 重原子数：
  64
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  259
• 氢给体数：
  9
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  surugamides C 在 盐酸 作用下， 以 水 为溶剂， 生成 D-丙氨酸 、 L-缬氨酸 、 D-亮氨酸 、 L-异亮氨酸 、 D-异亮氨酸 、 L-赖氨酸 、 D-苯丙氨酸
  参考文献：
  名称：

  Surugamides A–E, Cyclic Octapeptides with Four d-Amino Acid Residues, from a Marine Streptomyces sp.: LC–MS-Aided Inspection of Partial Hydrolysates for the Distinction of d- and l-Amino Acid Residues in the Sequence

  摘要：

  Surugamides A-E (1-5), cyclic octapeptides with four D-amino acid residues, were isolated from the broth of marine-derived Streptomyces sp. Their planar structures were determined by analyses of spectroscopic data, and the absolute configuration of constituent amino acid residues was determined by the Marfey's method. Differentiation of D-Ile and L-Ile in the sequence was established by chiral analysis of fragment peptides obtained from the partial hydrolysate, whose identification was conducted by LC-MS/MS.

  DOI：

  10.1021/jo400708u
• 作为产物：
  描述：

  Fmoc-L-缬氨酸 、 Fmoc-L-异亮氨酸 、 Fmoc-D-丙氨酸 、 Fmoc-D-亮氨酸 、 FMOC-赖氨酸 、 Fmoc-D-苯丙氨酸 、 Fmoc-D-异亮氨酸 在 2-肟氰乙酸乙酯 、 N,N'-二异丙基碳二亚胺 、 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 surugamides C
  参考文献：
  名称：

  SurE肽环化酶的N端底物特异性

  摘要：

  SurE 是一种独立的肽环化酶，对于生产 surugamide 抗生素至关重要。尽管 SurE在体内催化各种非核糖体肽的环化，但对其底物特异性知之甚少。为了解决这个问题，开发了一种树脂上的 SurE 环化测定，并结合 SNAC 硫酯和动力学测量来定义 N 末端底物残基的化学空间。

  DOI：

  10.1039/d2ob01061e

文献信息

• Surugamides A–E, Cyclic Octapeptides with Four <scp>d</scp>-Amino Acid Residues, from a Marine Streptomyces sp.: LC–MS-Aided Inspection of Partial Hydrolysates for the Distinction of <scp>d</scp>- and <scp>l</scp>-Amino Acid Residues in the Sequence
  作者：Kentaro Takada、Akihiro Ninomiya、Masato Naruse、Yi Sun、Masayuki Miyazaki、Yuichi Nogi、Shigeru Okada、Shigeki Matsunaga

  DOI：10.1021/jo400708u

  日期：2013.7.5

  Surugamides A-E (1-5), cyclic octapeptides with four D-amino acid residues, were isolated from the broth of marine-derived Streptomyces sp. Their planar structures were determined by analyses of spectroscopic data, and the absolute configuration of constituent amino acid residues was determined by the Marfey's method. Differentiation of D-Ile and L-Ile in the sequence was established by chiral analysis of fragment peptides obtained from the partial hydrolysate, whose identification was conducted by LC-MS/MS.
• The N-terminal substrate specificity of the SurE peptide cyclase
  作者：Asif Fazal、Jake Wheeler、Michael E. Webb、Ryan F. Seipke

  DOI：10.1039/d2ob01061e

  日期：——

  SurE is a standalone peptide cyclase essential for the production of surugamide antibiotics. Although SurE catalyses the cyclisation of varied nonribosomal peptides in vivo, its substrate specificity is poorly understood. To address this issue, an on-resin SurE cyclisation assay was developed and in combination with SNAC thioesters and kinetic measurements was used to define the chemical space of the

  SurE 是一种独立的肽环化酶，对于生产 surugamide 抗生素至关重要。尽管 SurE在体内催化各种非核糖体肽的环化，但对其底物特异性知之甚少。为了解决这个问题，开发了一种树脂上的 SurE 环化测定，并结合 SNAC 硫酯和动力学测量来定义 N 末端底物残基的化学空间。