N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester | 603128-68-3

• 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: N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester
• CAS: 603128-68-3
• 化学式: C₁₇H₂₉ClN₂O₅
• 分子量: 376.881
• InChiKey: GNHCVZXDQMXXMN-OLZOCXBDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.45
• 重原子数：
  25.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  84.94
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester 在 lithium hydroxide 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(thymin-1-ylacetyl)glycine
  参考文献：
  名称：

  Synthesis and Evaluation of (1S,2R/1R,2S)-Aminocyclohexylglycyl PNAs as Conformationally Preorganized PNA Analogues for DNA/RNA Recognition

  摘要：

  Conformationally constrained cis-aminocyclohexylglycyl PNAs have been designed on the basis of stereospecific imposition of 1,2-cis-cyclohexyl moieties on the aminoethyl segment of aminoethylglycyl PNA (aegPNA). The introduction of the cis-cyclohexyl ring may allow the restriction of the torsion angle beta in the ethylenediamine segment to 60-70degrees that is prevalent in PNA(2):DNA and PNA:RNA complexes. The synthesis of the optically pure monomers (10a and 10b) is achieved by stereoselective enzymatic hydrolysis of an intermediate ester 2. The chiral PNA oligomers were synthesized with (1S,2R/1R,2S)-aminocyclohexylglycyI thymine monomers in the center and N-terminus of aegPNA. Differential gel shift retardation with one or more units of modified monomer units was observed as a result of hybridization of PNA sequences with complementary DNA sequences. Hybridization studies with complementary DNA and RNA sequences using UV-T-m measurements indicate that PNA with (1S,2R)-cyclohexyl stereochemistry enhances selective binding with RNA over DNA as compared to control aegPNA and PNA with the other (1R,2S) isomer.

  DOI：

  10.1021/jo035747x
• 作为产物：
  描述：

  ((1R,2S)-2-氨基环己基)氨基甲酸叔丁酯 在 potassium fluoride 、 sodium carbonate 作用下， 以 1,4-二氧六环 、 水 、 乙腈 为溶剂， 反应 4.5h， 生成 N-[(2R)-tert-butyloxycarbonylaminocyclohex-(1S)-yl]-N-(chloroacetyl)glycine ethyl ester
  参考文献：
  名称：

  (1S,2R/1R,2S)-Aminocyclohexyl Glycyl Thymine PNA:  Synthesis, Monomer Crystal Structures, and DNA/RNA Hybridization Studies

  摘要：

  graphicThe synthesis of ethyl cis-(1S,2R/1R,2S)-2-aminocyclohex-1-yl-N-(thymin-1-yl-acetyl) glycinate (10a and 10b) via enzymatic resolution of the key racemic intermediate trans-2-azido cyclohexanols 3 is reported. The crystal structures of 10 show equatorial disposition of the tertiary amide group, with the torsion angle beta in the range 60-70degrees. The PNA oligomers incorporating these show differential effects in hybridizing with complementary DNA and RNA.

  DOI：

  10.1021/ol034933m