N¹-hexadecanoyl-(N⁴,N⁹,N¹³,N¹⁶-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane | 201984-83-0

• 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: N¹-hexadecanoyl-(N⁴,N⁹,N¹³,N¹⁶-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane
• 英文别名: tert-butyl N-[3-(hexadecanoylamino)propyl]-N-[3-[(2-methylpropan-2-yl)oxycarbonyl-[4-[(2-methylpropan-2-yl)oxycarbonyl-[3-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]amino]butyl]amino]propyl]carbamate
• CAS: 201984-83-0
• 化学式: C₄₉H₉₅N₅O₉
• 分子量: 898.321
• InChiKey: ZDVBLPHBKGUBQF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12
• 重原子数：
  63
• 可旋转键数：
  39
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  156
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  三氟乙酸 、 N¹-hexadecanoyl-(N⁴,N⁹,N¹³,N¹⁶-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane 以 二氯甲烷 为溶剂， 反应 2.0h， 以55%的产率得到N¹-hexadecanoyl-1,16-diamino-4,9,13-triazahexadecane tetratrifluoroacetate
  参考文献：
  名称：

  Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes

  摘要：

  Polyamine amides are useful in gene delivery as synthetic (non-viral) vectors or mimics of polycationic histones. The application of a homologation strategy, based upon reductive alkylation, allows unsymmetrical polyamine amides to be prepared in good yield. The interaction of this polyamine amide with calf thymus DNA was demonstrated in an ethidium bromide fluorescence quenching assay. (C) 1997 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(97)10543-3
• 作为产物：
  描述：

  1-trifluoroacetyl-5,10,14-tris-Boc-spermine 在 palladium dihydroxide ammonium hydroxide 、 氢气 、 sodium cyanoborohydride 、 1-羟基苯并三唑 、 溶剂黄146 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 61.0h， 生成 N¹-hexadecanoyl-(N⁴,N⁹,N¹³,N¹⁶-tetra-tert-butoxycarbonyl)-1,16-diamino-4,9,13-triazahexadecane
  参考文献：
  名称：

  Homologation of Polyamines in the Rapid Synthesis of Lipospermine Conjugates and Related Lipoplexes

  摘要：

  Lipopolyamine amides are useful cationic Lipids, synthetic vectors for non-viral gene delivery. Desymmetrisation of readily available symmetrical polyamines is an important first step in the synthesis of such compounds. The application of trifluoroacetyl as a protecting group allows unsymmetrical polyamine amides to be rapidly prepared. A reductive alkylation homologation strategy allows the sequential, regiocontrolled introduction of additional positive charges. Tetraamine spermine and other polyamine derivatives have been N-1-acylated with various single alkyl chains, and their relative binding affinities for DNA determined using an ethidium bromide displacement assay. The important effects on DNA binding affinity of the number of positive charges on the polyamine moiety and also the nature (chain length and degree of unsaturation) of the covalently attached lipid are demonstrated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)01082-0

文献信息

• Homologation of Polyamines in the Rapid Synthesis of Lipospermine Conjugates and Related Lipoplexes
  作者：Andrew J Geall、Ian S Blagbrough

  DOI：10.1016/s0040-4020(99)01082-0

  日期：2000.4

  Lipopolyamine amides are useful cationic Lipids, synthetic vectors for non-viral gene delivery. Desymmetrisation of readily available symmetrical polyamines is an important first step in the synthesis of such compounds. The application of trifluoroacetyl as a protecting group allows unsymmetrical polyamine amides to be rapidly prepared. A reductive alkylation homologation strategy allows the sequential, regiocontrolled introduction of additional positive charges. Tetraamine spermine and other polyamine derivatives have been N-1-acylated with various single alkyl chains, and their relative binding affinities for DNA determined using an ethidium bromide displacement assay. The important effects on DNA binding affinity of the number of positive charges on the polyamine moiety and also the nature (chain length and degree of unsaturation) of the covalently attached lipid are demonstrated. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Homologation of polyamines in the synthesis of lipo-spermine conjugates and related lipoplexes
  作者：Andrew J. Geall、Ian S. Blagbrough

  DOI：10.1016/s0040-4039(97)10543-3

  日期：1998.1

  Polyamine amides are useful in gene delivery as synthetic (non-viral) vectors or mimics of polycationic histones. The application of a homologation strategy, based upon reductive alkylation, allows unsymmetrical polyamine amides to be prepared in good yield. The interaction of this polyamine amide with calf thymus DNA was demonstrated in an ethidium bromide fluorescence quenching assay. (C) 1997 Elsevier Science Ltd. All rights reserved.