N^α,N^ε-di-Boc-D-Lys-OSu | 65581-52-4

• 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,N^ε-di-Boc-D-Lys-OSu
• 英文别名: di-BOC-D-lysine, N-hydroxysuccinimide ester；(Boc)2-D-Lys-OSu；N-alpha,N-epsilon-Bis-Boc-D-lysine N-hydroxysuccinimide ester；(2,5-dioxopyrrolidin-1-yl) (2R)-2,6-bis[(2-methylpropan-2-yl)oxycarbonylamino]hexanoate
• CAS: 65581-52-4
• 化学式: C₂₀H₃₃N₃O₈
• 分子量: 443.497
• InChiKey: IQVLXQGNLCPZCL-CYBMUJFWSA-N

物化性质

• 密度：
  1.21±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  31
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  140
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N^α,N^ε-di-Boc-D-Lys-OSu 在 4-二甲氨基吡啶 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 64.0h， 生成
  参考文献：
  名称：

  Heparin versus DNA: Chiral Preferences in Polyanion Binding to Self-Assembled Multivalent (SAMul) Nanostructures

  摘要：

  This communication presents simple cationic self-assembling multivalent (SAMul) first generation dendrons based on L or D lysine, which form identical nanoscale assemblies in terms of dimensions and charge densities but toward which DNA and heparin exhibit different chiral binding preferences. However, higher generation dendrons with larger hydrophilic head groups are bound identically by these polyanions, irrespective of chirality. We propose that well-organized chiral ligands on the surface of self-assembled nanostructures can exhibit enantioselective polyanion binding. This demonstrates that small structural changes can be amplified by self-assembly and impact on nanoscale binding.

  DOI：

  10.1021/jacs.5b04344
• 作为产物：
  描述：

  N-羟基丁二酰亚胺 、 N2,N6-双-Boc-D-赖氨酸 在 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 18.0h， 生成 N^α,N^ε-di-Boc-D-Lys-OSu
  参考文献：
  名称：

  WO2006/136460

  摘要：

  公开号：

文献信息

• Substitution of Amino Acids 1 and 3 in Teicoplanin Aglycon: Synthesis and Antibacterial Activity of Three First Non-natural Dalbaheptides.
  作者：ADRIANO MALABARBA、ROMEO CIABATTI、ERMINIO GERLI、FRANCA RIPAMONTI、PIETRO FERRARI、LUIGI COLOMBO、EUGENIA N. OLSUFYEVA、ANDREY Y. PAVLOV、MARINA I. REZNIKOVA、EDUARD I. LAZHKO、MARIA N. PREOBRAZHENSKAYA

  DOI：10.7164/antibiotics.50.70

  日期：——

  t staphylococci. As a preliminary approach, the substitution of amino acid 1 of deglucoteicoplanin (TD) with D-lysine or D-methylleucine and of its amino acid 3 with L-phenylalanine or L-lysine was investigated. In this paper, the synthesis and in vitro antibacterial activities of first non-natural dalbaheptide methyl ester aglycons MDL 63,166 (D-Lys1-Phe-3-TD-DHP-Me), MDL 64,945 (D-Lys1-Lys3-TD-DHP-Me)

  用新氨基酸或其他适合与耐糖肽（D-Ala-D-乳酸）和易感（D-Ala-D-Ala）相互作用的其他化学实体替换糖肽抗生素（dalbaheptides）的氨基酸1和3靶标是目前遵循的化学策略之一，以追求对高度糖肽耐药的VanA肠球菌的活性，同时保持对糖肽敏感的革兰氏阳性细菌（特别是耐甲氧西林的葡萄球菌）的活性。作为一种初步方法，研究了用D-赖氨酸或D-甲基亮氨酸取代去葡糖二十碳素（TD）的氨基酸1及其被L-苯丙氨酸或L-赖氨酸取代的氨基酸3。本文研究了首个非天然达巴肽甲基酯糖苷配基MDL 63,166（D-Lys1-Phe-3-TD-DHP-Me）的合成和体外抗菌活性，描述了MDL 64,945（D-Lys1-Lys3-TD-DHP-Me）和MDL 64,468（D-MeLeu1-Lys3-TD-DHP-Me）。这些化合物根据9步的总体操作步骤从中间体TD衍生的四肽甲酯（TDTP-Me）获得
• A Modification of the N-Terminal Amino Acid in me Eremomycin Aglycone.
  作者：O. V. MIROSHNIKOVA、T. F. BERDNIKOVA、E. N. OLSUFYEVA、A. Y. PAVLOV、M. I. REZNIKOVA、M. N. PREOBRAZHENSKAYA、R. CIABATTI、A. MALABARBA、L. COLOMBO

  DOI：10.7164/antibiotics.49.1157

  日期：——

  An Edman degradation of the antibiotic eremomycin aglycone produced the corresponding hexapeptide, which was aminoacylated with D-lysine, D-histidine or D-tryptophan derivatives to give new hep tapep tide analogs of the eremomycin aglycone. The aminoacylation of the eremomycin aglycone produced an octapeptide analog. The substitution of D-lysine for the N-terminal N-methyl-D-leucine does not seriously affect the in vitro antibacterial properties of the eremomycin aglycone whereas the heptapeptides with the N-terminal D-tryptophan or D-histidine moieties and the octapeptide with the N-terminal D-lysine are practically devoid of the antibacterial properties.

  埃德曼降解抗生素埃利霉素糖苷产生了相应的六肽，该六肽与D-赖氨酸、D-组氨酸或D-色氨酸衍生物氨基酰化，从而产生了埃利霉素糖苷的新型肝素类似物。埃利霉素糖苷的氨基酰化产生了八肽类似物。用D-赖氨酸取代N-端N-甲基-D-亮氨酸不会严重影响埃利霉素糖苷的体外抗菌特性，而N-端D-色氨酸或D-组氨酸部分的多肽和N-端D-赖氨酸的多肽实际上没有抗菌特性。
• WO2006/136460
  申请人：——

  公开号：——

  公开（公告）日：——
• Heparin versus DNA: Chiral Preferences in Polyanion Binding to Self-Assembled Multivalent (SAMul) Nanostructures
  作者：Stephen M. Bromfield、David K. Smith

  DOI：10.1021/jacs.5b04344

  日期：2015.8.19

  This communication presents simple cationic self-assembling multivalent (SAMul) first generation dendrons based on L or D lysine, which form identical nanoscale assemblies in terms of dimensions and charge densities but toward which DNA and heparin exhibit different chiral binding preferences. However, higher generation dendrons with larger hydrophilic head groups are bound identically by these polyanions, irrespective of chirality. We propose that well-organized chiral ligands on the surface of self-assembled nanostructures can exhibit enantioselective polyanion binding. This demonstrates that small structural changes can be amplified by self-assembly and impact on nanoscale binding.