(+/-)-gizzerosine | 88252-77-1

• 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: (+/-)-gizzerosine
• 英文别名: L-Gizzerosine；2-amino-6-[2-(1H-imidazol-5-yl)ethylamino]hexanoic acid
• CAS: 88252-77-1
• 化学式: C₁₁H₂₀N₄O₂
• 分子量: 240.305
• InChiKey: LFNFNJYYTXESHV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.6
• 重原子数：
  17
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  104
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+/-)-gizzerosine 、 sodium;1-[3-(4-hydroxy-3-(125I)iodanylphenyl)propanoyloxy]-2,5-dioxopyrrolidine-3-sulfonate 在 sodium disulfite 作用下， 以 二甲基亚砜 为溶剂， 反应 0.5h， 生成 2-[3-(4-hydroxy-3-(125I)iodanylphenyl)propanoylamino]-6-[2-(1H-imidazol-5-yl)ethylamino]hexanoic acid
  参考文献：
  名称：

  Procedure for Radiolabeling Gizzerosine and Basis for a Radioimmunoassay

  摘要：

  A method for the labeling of gizzerosine (GZ), a biogenic amine found in fish meal, is described. The labeling procedure with I-125 using a water-soluble Bolton-Hunter reagent and a mild water-insoluble oxidant (Iodogen) reagent is rapid and reproducible. The I-125-GZ hapten was demonstrated to be immunologically active in a radioimmunoassay developed with polyclonal antibodies to GZ absorbed with a histamine-Sepharose column. The curves were linear in the range of 0.0001 and 0.1 mu g/mL. Samples of fish meal previously extracted of histamine with methanol and submitted to acid hydrolysis were contaminated with known amounts of GZ and submitted to the assay. The fish meal samples contaminated with GZ show a dose-response effect similar to the standard curve, and apparently the other component present in the sample did not interfere with the binding of the antibodies to I-125-GZ. These data indicate the suitability of the radioimmunoassay to determine specifically GZ in fish meal.

  DOI：

  10.1021/jf981336j
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 以150 mg的产率得到(+/-)-gizzerosine
  参考文献：
  名称：

  合成的外消旋和旋光形式的鸟嘌呤肌苷，是雏鸡的izz肌侵蚀的诱因

  摘要：

  合成了外消旋体和吡咯烷磺酸[2-氨基-9-（4-咪唑基）-7-氮杂壬酸]的（R）-和（S）-形式，并将（S）-异构体鉴定为有毒物质鱼粉中的这种物质会导致小鸡严重的izz侵蚀（黑呕吐物）。

  DOI：

  10.1016/s0040-4020(01)96782-1

文献信息

• OHTA, YOSHIO;OHASHI, HIDEO;ENOMOTO, SETSUKO;MACHIDA, YOSHIAKI, AGR. AND BIOL. CHEM., 52,(1988) N1, C. 2817-2821
  作者：OHTA, YOSHIO、OHASHI, HIDEO、ENOMOTO, SETSUKO、MACHIDA, YOSHIAKI

  DOI：——

  日期：——
• JPS59176264A
  申请人：——

  公开号：JPS59176264A

  公开（公告）日：1984-10-05
• Synthesis of the racemic and optically active forms of gizzerosine, the inducer of gizzard erosion in chicks
  作者：Kenji Mori、Takeshi Sugai、Yukari Maeda、Tomomi Okazaki、Tadashi Noguchi、Hiroshi Naito

  DOI：10.1016/s0040-4020(01)96782-1

  日期：1985.1

  The racemate and both the (R)- and (S)-forms of gizzerosine [2-amino-9-(4-imidazolyl)-7-azanonanoic acid] were synthesised, and the (S)-isomer was identified as the toxic substance in fish meal causing severe gizzard erosion (black vomit) in chicks.

  合成了外消旋体和吡咯烷磺酸[2-氨基-9-（4-咪唑基）-7-氮杂壬酸]的（R）-和（S）-形式，并将（S）-异构体鉴定为有毒物质鱼粉中的这种物质会导致小鸡严重的izz侵蚀（黑呕吐物）。
• Procedure for Radiolabeling Gizzerosine and Basis for a Radioimmunoassay
  作者：Marcela Torres、Headdy Manosalva、Isabel Carrasco、Alfredo E. De Ioannes、María Inés Becker

  DOI：10.1021/jf981336j

  日期：1999.10.1

  A method for the labeling of gizzerosine (GZ), a biogenic amine found in fish meal, is described. The labeling procedure with I-125 using a water-soluble Bolton-Hunter reagent and a mild water-insoluble oxidant (Iodogen) reagent is rapid and reproducible. The I-125-GZ hapten was demonstrated to be immunologically active in a radioimmunoassay developed with polyclonal antibodies to GZ absorbed with a histamine-Sepharose column. The curves were linear in the range of 0.0001 and 0.1 mu g/mL. Samples of fish meal previously extracted of histamine with methanol and submitted to acid hydrolysis were contaminated with known amounts of GZ and submitted to the assay. The fish meal samples contaminated with GZ show a dose-response effect similar to the standard curve, and apparently the other component present in the sample did not interfere with the binding of the antibodies to I-125-GZ. These data indicate the suitability of the radioimmunoassay to determine specifically GZ in fish meal.