dimethyl 2,5-diaminohexanedioate dihydrochloride | 1069-28-9

• 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: dimethyl 2,5-diaminohexanedioate dihydrochloride
• 英文别名: 2,5-diamino-adipic acid dimethyl ester; hydrochloride；2,5-Diamino-adipinsaeure-dimethylester; Hydrochlorid
• CAS: 1069-28-9
• 化学式: C₈H₁₆N₂O₄*2ClH
• 分子量: 277.148
• InChiKey: JLDAPLOXJNWLSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.81
• 重原子数：
  15.0
• 可旋转键数：
  5.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  104.64
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  dimethyl 2,5-diaminohexanedioate dihydrochloride 在 六甲基磷酰三胺 、 正丁基锂 、 三乙胺 、 二异丙胺 、 三氟乙酸 、 potassium iodide 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.83h， 生成 dimethyl (2S,5S)-2,5-diamino-2,5-bis[4-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)butyl]hexanedioate
  参考文献：
  名称：

  Biomimetic Design Results in a Potent Allosteric Inhibitor of Dihydrodipicolinate Synthase from Campylobacter jejuni

  摘要：

  Dihydrodipicolinate synthase (DHDPS), an enzyme required for bacterial peptidoglycan biosynthesis, catalyzes the condensation of pyruvate and beta-aspartate semialdehyde (ASA) to form a cyclic product which dehydrates to form dihydrodipicolinate. DHDPS has, for several years, been considered a putative target for novel antibiotics. We have designed the first potent inhibitor of this enzyme by mimicking its natural allosteric regulation by lysine, and obtained a crystal structure of the protein inhibitor complex at 2.2 angstrom resolution. This novel inhibitor, which we named "bislysine", resembles two lysine molecules linked by an ethylene bridge between the alpha-carbon atoms. Bislysine is a mixed partial inhibitor with respect to the first substrate, pyruvate, and a noncompetitive partial inhibitor with respect to ASA, and binds to all forms of the enzyme with a K-i near 200 nM, more than 300 times more tightly than lysine. Hill plots show that the inhibition is cooperative, indicating that the allosteric sites are not independent despite being located on opposite sides of the protein tetramer, separated by approximately 50 angstrom. A mutant enzyme resistant to lysine inhibition, Y110F, is strongly inhibited by this novel inhibitor, suggesting this may be a promising strategy for antibiotic development.

  DOI：

  10.1021/jacs.5b12695
• 作为产物：
  描述：

  己二酸 在 盐酸 、 氯化亚砜 、 sodium azide 、 水 、 溴 、 三苯基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 dimethyl 2,5-diaminohexanedioate dihydrochloride
  参考文献：
  名称：

  2-异硫氰酸根合羧酸酯的烯醇化物：噻唑并[5,4-d]-噻唑衍生物和2-硫代-1,3-噻唑烷-4-羧酸酯的合成

  摘要：

  摘要 衍生自2-异硫代羧酸薄荷酯的烯醇钛（IV）的氧化二聚作用导致自由基偶联，然后环化。该级联反应得到作为纯对映异构体的噻唑并[5,4- d ]噻唑衍生物。在相似的条件下，2-异硫氰酸根合羧酸的2-甲基丁酯进行分子间氧化二聚生成噻唑并[5,4- d]thiazoles and 2,3-diisothiocyanatosuccinates. Application of the soft enolization technique to dimethyl α,α′-diisothiocyanatodicarboxylic esters gives novel cyclic 1,2-diisothiocyanato-1,2-dicarboxylates. Sodium enolates of 2-isothiocyanatocarboxylates, on the other hand, form

  DOI：

  10.1055/s-0031-1290825

文献信息

• Eastwood, Frank W.; Gunawardana, Dionne; Wernert, Gregory T., Australian Journal of Chemistry, 1982, vol. 35, # 11, p. 2289 - 2298
  作者：Eastwood, Frank W.、Gunawardana, Dionne、Wernert, Gregory T.

  DOI：——

  日期：——