N^α-9-fluorenylmethoxycarbonyl-(N^ε-tert-butoxycarbonyl)lysylglycylglycine | 194992-01-3

• 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^α-9-fluorenylmethoxycarbonyl-(N^ε-tert-butoxycarbonyl)lysylglycylglycine
• 英文别名: Fmoc-Lys(Boc)-Gly-Gly-OH；2-[[2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-6-[(2-methylpropan-2-yl)oxycarbonylamino]hexanoyl]amino]acetyl]amino]acetic acid
• CAS: 194992-01-3
• 化学式: C₃₀H₃₈N₄O₈
• 分子量: 582.654
• InChiKey: LYSKXNJXIVNXCT-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  42
• 可旋转键数：
  16
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N^α-9-fluorenylmethoxycarbonyl-(N^ε-tert-butoxycarbonyl)lysylglycylglycine 在 N,N'-二环己基碳二亚胺 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 生成 (S)-6-Amino-2-(3-{7-[2-(2-amino-acetylamino)-ethyl]-1,3,6,8-tetraoxo-3,6,7,8-tetrahydro-1H-benzo[lmn][3,8]phenanthrolin-2-yl}-propionylamino)-hexanoic acid
  参考文献：
  名称：

  A New Class of Polyintercalating Molecules

  摘要：

  We have synthesized a series of polyintercalating compounds, including the first known tetraintercalator, based on the 1,4,5,8-naphthalenetetracarboxylic diimide chromophore. The chromophores are attached in a head-to-tail arrangement by peptide linkers and are synthesized by standard solid phase peptide synthesis methods. We report evidence, based on UV-visible spectroscopy and viscometry, that the compounds are fully intercalated upon binding to double-stranded DNA. Using DNAse I footprinting experiments, the bisintercalator 2 was found to bind to DNA in a cooperative manner. The footprinting results as well as association and dissociation kinetics data reveal that the compounds exhibit a tremendous preference for GC over AT sequences. A. mode of binding is proposed in which the compounds intercalate completely from the major groove, and not in a threading manner as may be suggested by their structures. A kinetic scheme is proposed that takes into account the observed cooperativity and fits the data for the dissociations of the polyintercalators from poly(dAdT), although a similar scheme could not adequately model their dissociations from poly(dGdC) or from calf thymus DNA.

  DOI：

  10.1021/ja9706108
• 作为产物：
  描述：

  {2-[(S)-6-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)-hexanoylamino]-acetylamino}-acetic acid benzyl ester 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 3.0h， 生成 N^α-9-fluorenylmethoxycarbonyl-(N^ε-tert-butoxycarbonyl)lysylglycylglycine
  参考文献：
  名称：

  An octakis-intercalating molecule

  摘要：

  Herein we report the synthesis and characterization of a polyintercalator with eight potential intercalating 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) units linked in a head-to-tail arrangement via a peptide linker. W spectroscopy and viscometry measurements indicated the molecule binds to double-stranded DNA with all eight NDI units intercalated simultaneously. Competition dialysis and DNAse 1 footprinting studies revealed a preference for GC-rich regions of DNA, and circular dichroism studies revealed significant distortion of B-form DNA upon binding. Our so-called 'octamer' represents, to the best of our knowledge, the first intercalator that binds as an octakis-intercalator, capable of spanning at least 16 base pairs of DNA. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(00)00335-7

文献信息

• A New Class of Polyintercalating Molecules
  作者：R. Scott Lokey、Yan Kwok、Vladimir Guelev、Christopher J. Pursell、Laurence H. Hurley、Brent L. Iverson

  DOI：10.1021/ja9706108

  日期：1997.8.1

  We have synthesized a series of polyintercalating compounds, including the first known tetraintercalator, based on the 1,4,5,8-naphthalenetetracarboxylic diimide chromophore. The chromophores are attached in a head-to-tail arrangement by peptide linkers and are synthesized by standard solid phase peptide synthesis methods. We report evidence, based on UV-visible spectroscopy and viscometry, that the compounds are fully intercalated upon binding to double-stranded DNA. Using DNAse I footprinting experiments, the bisintercalator 2 was found to bind to DNA in a cooperative manner. The footprinting results as well as association and dissociation kinetics data reveal that the compounds exhibit a tremendous preference for GC over AT sequences. A. mode of binding is proposed in which the compounds intercalate completely from the major groove, and not in a threading manner as may be suggested by their structures. A kinetic scheme is proposed that takes into account the observed cooperativity and fits the data for the dissociations of the polyintercalators from poly(dAdT), although a similar scheme could not adequately model their dissociations from poly(dGdC) or from calf thymus DNA.
• An octakis-intercalating molecule
  作者：M Murr

  DOI：10.1016/s0968-0896(00)00335-7

  日期：2001.5

  Herein we report the synthesis and characterization of a polyintercalator with eight potential intercalating 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) units linked in a head-to-tail arrangement via a peptide linker. W spectroscopy and viscometry measurements indicated the molecule binds to double-stranded DNA with all eight NDI units intercalated simultaneously. Competition dialysis and DNAse 1 footprinting studies revealed a preference for GC-rich regions of DNA, and circular dichroism studies revealed significant distortion of B-form DNA upon binding. Our so-called 'octamer' represents, to the best of our knowledge, the first intercalator that binds as an octakis-intercalator, capable of spanning at least 16 base pairs of DNA. (C) 2001 Elsevier Science Ltd. All rights reserved.