8-amino-7-oxononanoic acid hydrochloride | 177408-66-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-amino-7-oxononanoic acid hydrochloride
• 英文别名: (S)-8-amino-7-oxononanoic acid hydrochloride；(8S)-8-amino-7-oxononanoic acid;hydrochloride
• CAS: 177408-66-1；177408-65-0
• 化学式: C₉H₁₇NO₃*ClH
• 分子量: 223.7
• InChiKey: ZGPOLJARQCHVLY-FJXQXJEOSA-N

物化性质

• 熔点：
  134-136
• 溶解度：
  甲醇（微溶）、水（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  1.36
• 重原子数：
  14
• 可旋转键数：
  7
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  80.4
• 氢给体数：
  3
• 氢受体数：
  4

安全信息

• 海关编码：
  2922509090

反应信息

• 作为反应物：
  描述：

  8-amino-7-oxononanoic acid hydrochloride 在 碳酸氢钠 、 乙酰氯 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 8-tert-butoxycarbonylamino-7-oxononanoic acid methyl ester
  参考文献：
  名称：

  The Synthesis of the Vitamers of Biotin

  摘要：

  An efficient synthetic pathway for the preparation of the vitamers of biotin which provides easy access to optically pure KAPA as well as diastereomeric mixtures of DAPA, DTB, and analogs thereof has been developed. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1094
• 作为产物：
  描述：

  乙基5-碘戊酸酯 在 盐酸 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 6.0h， 生成 8-amino-7-oxononanoic acid hydrochloride
  参考文献：
  名称：

  The Synthesis of the Vitamers of Biotin

  摘要：

  An efficient synthetic pathway for the preparation of the vitamers of biotin which provides easy access to optically pure KAPA as well as diastereomeric mixtures of DAPA, DTB, and analogs thereof has been developed. (C) 1998 Academic Press.

  DOI：

  10.1006/bioo.1998.1094

文献信息

• First synthesis of both enantiomers of the biotin vitamer 8-amino-7-oxopelargonic acid
  作者：Denis Lucet、Thierry Le Gall、Charles Mioskowski、Olivier Ploux、Andrée Marquet

  DOI：10.1016/0957-4166(96)00098-5

  日期：1996.4

  A short and efficient synthesis of both 8-amino-7-oxopelargonic acid enantiomers from d or l-alanine is presented. The key step of this first chemical synthesis is the non-racemizing Horner-Wadsworth-Emmons reaction of a β-ketophosphonate 3 and benzyl 4-formylbutanoate. The growth-promoting effect of the enantiomers was tested on Saccharomyces cerevisiae.

  提出了由d或1-丙氨酸短而有效地合成两种8-氨基-7-氧代壬酸对映体的方法。该第一化学合成的关键步骤是β-酮膦酸酯3和4-甲酰基丁酸酯苄基的非消旋霍纳-沃兹沃思-埃蒙斯反应。测试了对映异构体对酿酒酵母的促进生长的作用。
• The design and synthesis of inhibitors of dethiobiotin synthetase as potential herbicides
  作者：Alan R Rendina、Wendy S Taylor、Katharine Gibson、George Lorimer、Dennis Rayner、Bruce Lockett、Kevin Kranis、Barry Wexler、Dana Marcovici-Mizrahi、Ayelet Nudelman、Abraham Nudelman、Eileen Marsilii、Hongji Chi、Zdislaw Wawrzak、Joseph Calabrese、Weijun Huang、Jia Jia、Gunter Schneider、Ylva Lindqvist、Guang Yang

  DOI：10.1002/(sici)1096-9063(199903)55:3<236::aid-ps888>3.0.co;2-0

  日期：1999.3

  Dethiobiotin synthetase (DTBS;E.C. 6.6.6.6), the penultimate enzyme in the biosynthesis of the essential vitamin biotin, is a new potential target for novel herbicides. Inhibitors were designed based on mechanistic and structural information. The in-vitro activities of these potential inhibitors versus the bacterial enzyme are reported here. Mimics of 7,8-diaminopelargonic acid (DAPA) or the DAPA carbamate reaction intermediate were substrates or partial substrates for the enzyme. Synergistic binding with ATP was noted with compounds which contained an amino functionality, NMR studies and X-ray structures confirmed that the inhibitors could be phosphorylated by the enzyme. Several series of potential inhibitors were designed to take advantage of this partial substrate activity by generating potentially more tightly bound phosphorylated inhibitors in situ, Structure-activity relationships for these series based on both substrate and inhibitory activity are described herein. An X-ray structure for one of these inhibitors is also discussed. Although considerable potential for inhibitors of this type was demonstrated, none of the compounds reported showed sufficient herbicidal activity to be a commercial proposition. (C) 1999 Society of Chemical Industry.