(S)-2-[(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexylamino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester | 871815-65-5

• 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: (S)-2-[(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexylamino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester
• CAS: 871815-65-5
• 化学式: C₃₄H₄₈Cl₂N₄O₈
• 分子量: 711.683
• InChiKey: UKLZPNJOXFFRMG-UHSQPCAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.51
• 重原子数：
  48.0
• 可旋转键数：
  19.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  153.32
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (S)-2-[(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexylamino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 生成 (S)-2-[(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexylamino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid
  参考文献：
  名称：

  Synthesis of new chiral PNAs bearing a dipeptide-mimic monomer with two lysine-derived stereogenic centres

  摘要：

  The synthesis of new chiral PNA analogues based on lysine is reported. In particular, L- and/or D-lysine-based PNA submonomers bearing two lysine side chains exactly spaced as in the dipeptide Lys-Lys were synthesized and incorporated in the middle of decameric PNA strands, obtaining four diastereomeric (LD, DL, LL and DD) lysine-based chiral PNAs. The hybridization with their complementary antiparallel DNA strand was studied by melting temperature determination and compared with the analogue achiral PNA and chiral PNAs bearing one residue with either of the two lysine enantiomers. The binding abilities were shown to be strongly dependent on the configuration of the stereogenic centres. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.157
• 作为产物：
  描述：

  Boc-N'-(2-氯苄氧羰基)-D-赖氨酸 在 盐酸 、 lithium aluminium tetrahydride 、 sodium cyanoborohydride 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 溶剂黄146 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 (S)-2-[(R)-2-tert-Butoxycarbonylamino-6-(2-chloro-benzyloxycarbonylamino)-hexylamino]-6-(2-chloro-benzyloxycarbonylamino)-hexanoic acid methyl ester
  参考文献：
  名称：

  Synthesis of new chiral PNAs bearing a dipeptide-mimic monomer with two lysine-derived stereogenic centres

  摘要：

  The synthesis of new chiral PNA analogues based on lysine is reported. In particular, L- and/or D-lysine-based PNA submonomers bearing two lysine side chains exactly spaced as in the dipeptide Lys-Lys were synthesized and incorporated in the middle of decameric PNA strands, obtaining four diastereomeric (LD, DL, LL and DD) lysine-based chiral PNAs. The hybridization with their complementary antiparallel DNA strand was studied by melting temperature determination and compared with the analogue achiral PNA and chiral PNAs bearing one residue with either of the two lysine enantiomers. The binding abilities were shown to be strongly dependent on the configuration of the stereogenic centres. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.09.157