(S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxo-2-pentenoate | 1210057-70-7

• 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: (S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxo-2-pentenoate
• CAS: 1210057-70-7
• 化学式: C₁₆H₂₇NO₅
• 分子量: 313.394
• InChiKey: VOAXVVNERNLFSN-GFCCVEGCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.87
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.07
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxo-2-pentenoate 在 palladium on activated charcoal 、 氢气 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 以100%的产率得到(1'R,4S)-4-(2'-ethoxycarbonyl-1'-methyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereochemical Assignment of Four Diastereoisomers of 3,4-Dimethylpyroglutamic Acid, a Moiety of Callipeltin B

  摘要：

  DOI：

  10.3987/com-14-13003
• 作为产物：
  描述：

  (R)-3-boc-4-(甲氧基甲基氨基甲酰)-2,2-二甲基噁唑啉 在 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 (S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxo-2-pentenoate
  参考文献：
  名称：

  Effects on polo-like kinase 1 polo-box domain binding affinities of peptides incurred by structural variation at the phosphoamino acid position

  摘要：

  Protein-protein interactions (PPIs) mediated by the polo-box domain (PBD) of polo-like kinase 1 (Plk1) serve important roles in cell proliferation. Critical elements in the high affinity recognition of peptides and proteins by PBD are derived from pThr/pSer-residues in the binding ligands. However, there has been little examination of pThr/pSer mimetics within a PBD context. Our current paper compares the abilities of a variety of amino acid residues and derivatives to serve as pThr/pSer replacements by exploring the role of methyl functionality at the pThr beta-position and by replacing the phosphoryl group by phosphonic acid, sulfonic acid and carboxylic acids. This work sheds new light on structure activity relationships for PBD recognition of phosphoamino acid mimetics. Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2012.05.036

文献信息

• Synthetic Studies on Callipeltins: Stereoselective Syntheses of (3S,4R)-3,4-Dimethyl-L-pyroglutamic Acid and Fmoc-D-allothreonine from Serine Derivatives
  作者：Hiroyuki Konno、Yoko Takebayashi、Kazuto Nosaka、Kenichi Akaji

  DOI：10.3987/com-09-11834

  日期：——

  The non-proteinogenic amino acids contained in callipeltins, (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid and D-allothreonine, were synthesized from D- or L-serine. The stereoselective synthesis of two methyl groups of (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid was accomplished by diastereoselective hydrogenation and alkylation. Kinetic epimerization of the C-4 methyl substituent followed by Boc-deprotection with 10% TFA gave the desired (3S, 4R)-3, 4-dimethyl-L-pyroglutamic acid as a single isomer.