erythrochelin | 1220040-60-7

• 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: erythrochelin
• 英文别名: (R)-2-acetamido-N-((R)-3-hydroxy-1-{hydroxy[3-((2S,5S)-5-[3-(Nhydroxyacetamido)propyl]-3,6-dioxopiperazin-2-yl)propyl]amino}-1-oxopropan-2-yl)-5-(N-hydroxyacetamido)pentanamide；D-α-N-acetyl-δ-N-acetyl-δ-N-hydroxyornithine-D-serine-cyclo(L-δ-N-hydroxyornithine-L-δ-N-acetyl-δ-N-hydroxyornithine)；Erythrochelin；(2R)-2-acetamido-5-[acetyl(hydroxy)amino]-N-[(2R)-1-[3-[(2S,5S)-5-[3-[acetyl(hydroxy)amino]propyl]-3,6-dioxopiperazin-2-yl]propyl-hydroxyamino]-3-hydroxy-1-oxopropan-2-yl]pentanamide
• CAS: 1220040-60-7
• 化学式: C₂₄H₄₁N₇O₁₁
• 分子量: 603.63
• InChiKey: OHIZVXAYPZKILQ-FUMNGEBKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -4
• 重原子数：
  42
• 可旋转键数：
  17
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  258
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  erythrochelin 、 magnesium chloride 以 甲醇 为溶剂， 生成
  参考文献：
  名称：

  Synthesis of Erythrochelin: A Hydroxamate-Type Siderophore from Saccharopolyspora erythraea

  摘要：

  Erythrochelin, a hydroxamate-type siderophore produced by Saccharopolyspora erythraea, is synthesized for the first time. A key building block of erythrochelin containing the 2,5-diketopiperazine ring is prepared by intramolecular cyclization of the corresponding dipeptide precursor derived from two kinds of protected delta-N-hydroxy-L-ornithines. Consecutive condensation of the building block with protected D-serine and protected delta-N-hydroxy-D-ornithine, followed by deprotection, furnishes erythrochelin.

  DOI：

  10.1055/s-0035-1560564
• 作为产物：
  描述：

  δ-N-benzyloxy-δ-N-(2,2,2-trichloroethoxy)carbonyl-L-ornithine methyl ester hydrochloride 在 盐酸 、 4-二甲氨基吡啶 、 palladium 10% on activated carbon 、 氨 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 三氟乙酸 、 锌 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 76.17h， 生成 erythrochelin
  参考文献：
  名称：

  Synthesis of Erythrochelin: A Hydroxamate-Type Siderophore from Saccharopolyspora erythraea

  摘要：

  Erythrochelin, a hydroxamate-type siderophore produced by Saccharopolyspora erythraea, is synthesized for the first time. A key building block of erythrochelin containing the 2,5-diketopiperazine ring is prepared by intramolecular cyclization of the corresponding dipeptide precursor derived from two kinds of protected delta-N-hydroxy-L-ornithines. Consecutive condensation of the building block with protected D-serine and protected delta-N-hydroxy-D-ornithine, followed by deprotection, furnishes erythrochelin.

  DOI：

  10.1055/s-0035-1560564

文献信息

• Erythrochelin - a hydroxamate-type siderophore predicted from the genome of Saccharopolyspora erythraea
  作者：Lars Robbel、Thomas A. Knappe、Uwe Linne、Xiulan Xie、Mohamed A. Marahiel

  DOI：10.1111/j.1742-4658.2009.07512.x

  日期：2010.2

  siderophores encompasses a multitude of structurally diverse natural products. The genome of the erythromycin‐producing strain Saccharopolyspora erythraea contains 25 secondary metabolite gene clusters that are mostly considered to be orphan, including two that are responsible for siderophore assembly. In the present study, we report the isolation and structural elucidation of the hydroxamate‐type tetrapeptide

  非核糖体组装的铁载体类包括多种结构多样的天然产物。产生红霉素的菌株Saccharopolyspora erythraea的基因组包含25个次级代谢产物基因簇，这些簇大多被认为是孤儿，包括两个负责铁载体组装的簇。在本研究中，我们报道了异羟肟酸酯型四肽铁载体赤藓红素的分离和结构解析，这是第一种非核糖体肽合成酶衍生的红细菌天然产物。为了替代传统的活性测定指导的新型次生代谢产物的分离，我们采用了专门的radio-LC-MS方法来鉴定工业相关菌株中隐性基因簇的非核糖体肽。该方法基于转录组数据和腺苷酸化域特异性预测，并导致检测到放射性标记的鸟氨酸继承异羟肟酸酯型铁载体。改善了铁载体的生成，可以通过NMR和MSn分析以及用于确定氨基酸构型的水解产物衍生化来阐明整体结构。四肽铁载体赤藓红素的序列被确定为d-N-乙酰基-δ-N-乙酰基-δ-N-羟基鸟氨酸-d-丝氨酸-环（l-δ-N-羟基鸟氨酸-l-δ-N
• Synthesis of Erythrochelin: A Hydroxamate-Type Siderophore from Saccharopolyspora erythraea
  作者：Shigeki Sano、Michiyasu Nakao、Shunsuke Tsuji、Syuji Kitaike

  DOI：10.1055/s-0035-1560564

  日期：——

  Erythrochelin, a hydroxamate-type siderophore produced by Saccharopolyspora erythraea, is synthesized for the first time. A key building block of erythrochelin containing the 2,5-diketopiperazine ring is prepared by intramolecular cyclization of the corresponding dipeptide precursor derived from two kinds of protected delta-N-hydroxy-L-ornithines. Consecutive condensation of the building block with protected D-serine and protected delta-N-hydroxy-D-ornithine, followed by deprotection, furnishes erythrochelin.