[(R)-6-(2-Amino-acetylamino)-7-phenyl-heptanoylamino]-acetic acid | 341508-60-9

• 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: [(R)-6-(2-Amino-acetylamino)-7-phenyl-heptanoylamino]-acetic acid
• CAS: 341508-60-9
• 化学式: C₁₇H₂₅N₃O₄
• 分子量: 335.403
• InChiKey: JFEAWKUUADDSHX-CQSZACIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  24.0
• 可旋转键数：
  11.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  121.52
• 氢给体数：
  4.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  [(R)-6-(2-Amino-acetylamino)-7-phenyl-heptanoylamino]-acetic acid 在 三乙胺 作用下， 生成 (13R)-13-benzyl-1,4,7-triazacyclotridecane-2,5,8-trione
  参考文献：
  名称：

  Synthesis and Conformation of Gly-Gly Dipeptides Constrained with Phenylalanine-like Aminocaproic Acid Linkers

  摘要：

  [GRAPHICS]The constraint of dipeptides with linkers derived from 6-aminocaproic acid (Aca) is a useful means of constructing a beta-turn peptidomimetic, The extension of this concept to the mimicry of a tripeptide entails the incorporation of a side chain moiety on either end of the Aca chain. The synthesis and conformational analysis of two exemplary compounds is discussed.

  DOI：

  10.1021/ol005618s
• 作为产物：
  描述：

  (6S)-6-benzyl-6-[N-(tert-butoxycarbonyl)]-hex-4-enoic acid ethyl ester 在 palladium on activated charcoal lithium hydroxide 、 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 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 乙酸乙酯 为溶剂， 20.0 ℃ 、241.32 kPa 条件下， 反应 7.5h， 生成 [(R)-6-(2-Amino-acetylamino)-7-phenyl-heptanoylamino]-acetic acid
  参考文献：
  名称：

  Effect of Progressive Benzyl Substitution on the Conformations of Aminocaproic Acid-Cyclized Dipeptides

  摘要：

  The constraint of dipeptides into a beta -turn conformation can be accomplished by linking the two ends of a standard dipeptide with a linker derived from aminocaproic acid (Aca). To elucidate the possibility of using substituted Aca linkers in peptidomimetic design, a series of five macrocycles composed of a monobenzylated Aca linker (containing the benzyl group on each of the five methylene groups of the parent linker) and Gly-Gly were synthesized. The requisite linkers were made by regiochemically controlled ring expansion techniques (for substitution on Aca positions C-3, C-4, or C-5), an Evans alkylation route (for C-2), or by chain extension of L-phenylalanal (for C-6). The solution-phase conformations of the macrocycles were examined by NMR and CD techniques; in addition, crystal structures of the C-4- and C-6-benzyl-substituted linkers were obtained. Four out of the five macrocycles were found to exist with the dipeptide portion taking up either a type II or II ' beta -turn conformation, but the Gly-Gly unit in the compound derived from 4-benzyl-Aca did not correspond to one of the standard beta -turn types.

  DOI：

  10.1021/jo001308b