(2S,3R)-2-Amino-3,5-dimethyl-hex-4-enoic acid | 1018928-87-4

• 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: (2S,3R)-2-Amino-3,5-dimethyl-hex-4-enoic acid
• 英文别名: (2S,3R)-2-amino-3,5-dimethylhex-4-enoic acid
• CAS: 1018928-87-4
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: ACJIBDJXENOACA-RQJHMYQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  11
• 可旋转键数：
  3
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  63.3
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (2S,3R)-2-Amino-3,5-dimethyl-hex-4-enoic acid 在 四(三苯基膦)钯 sodium carbonate 、 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 、 N-甲基苯胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 1.5h， 生成 (2S)-2-[[(2S,4R)-5-benzoyloxy-2-[[(2S,3R)-3-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S,3R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-3,5-dimethylhex-4-enoyl]amino]-3-[1-(2-methylbut-3-en-2-yl)indol-3-yl]propanoyl]-methylamino]-4-methylpentanoyl]amino]propanoic acid
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n
• 作为产物：
  描述：

  syn-N-trifluoroacetyl-2-(1-methyl-propenyl)glycine methyl ester 在 4-二甲氨基吡啶 、 lithium hydroxide 、 正丁基锂 、 碳酸氢钠 、 臭氧 、 一水合肼 、 三氟乙酸 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 为溶剂， 反应 28.0h， 生成 (2S,3R)-2-Amino-3,5-dimethyl-hex-4-enoic acid
  参考文献：
  名称：

  Total Synthesis of Cyclomarin C

  摘要：

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.

  DOI：

  10.1021/ol049065n

文献信息

• Asymmetric β‐Methylation of <scp>l</scp> ‐ and <scp>d</scp> ‐α‐Amino Acids by a Self‐Contained Enzyme Cascade
  作者：Cangsong Liao、Florian P. Seebeck

  DOI：10.1002/anie.201916025

  日期：2020.4.27

  AbstractThis report describes a modular enzyme‐catalyzed cascade reaction that transforms l‐ or d‐α‐amino acids to β‐methyl‐α‐amino acids. In this process an α‐amino acid transaminase, an α‐keto acid methyltransferase, and a halide methyltransferase cooperate in two orthogonal reaction cycles that mediate product formation and regeneration of the cofactor pyridoxal‐5′‐phosphate and the co‐substrate S‐adenosylmethionine. The only stoichiometric reagents consumed in this process are the unprotected l‐ or d‐α‐amino acid and methyl iodide.
• Total Synthesis of Cyclomarin C
  作者：Shi-Jun Wen、Zhu-Jun Yao

  DOI：10.1021/ol049065n

  日期：2004.8.1

  The total synthesis of cyclomarin C was accomplished through a convergent strategy from a tetrapeptide fragment and a tripeptide one. The developed methods to prepare the needed noncoded amino acids, the proper protection of peptide fragments, and identification of the optimum macrocylization site can be applied to further synthetic studies on other members of cyclomarins.