N^ε-benzyloxycarbonyl-N^α-dansyl-L-lysine | 38570-39-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N^ε-benzyloxycarbonyl-N^α-dansyl-L-lysine
• 英文别名: N_ε-Z-dansyl-L-lysine；N^ε-Cbz-N^α-dansyllisyne；Dan-Lys(Cbz)(Cbz)-OH；(2S)-2-[[5-(dimethylamino)naphthalen-1-yl]sulfonylamino]-6-(phenylmethoxycarbonylamino)hexanoic acid
• CAS: 38570-39-7
• 化学式: C₂₆H₃₁N₃O₆S
• 分子量: 513.615
• InChiKey: DSUIZRAVSMFCLD-QFIPXVFZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  13
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  133
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N^ε-benzyloxycarbonyl-N^α-dansyl-L-lysine 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 27.0h， 生成 (2R,4S,5R,6R)-5-Acetylamino-2-(2-{2-[(S)-6-benzyloxycarbonylamino-2-(5-dimethylamino-naphthalene-1-sulfonylamino)-hexanoylamino]-ethoxy}-ethoxy)-4-hydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Generation and in Situ Evaluation of Libraries of Poly(acrylic acid) Presenting Sialosides as Side Chains as Polyvalent Inhibitors of Influenza-Mediated Hemagglutination

  摘要：

  This paper describes a simple, microscale method for generating and evaluating libraries of derivatives of poly(acrylic acid) (pAA) that present mixtures of side chains that influence their biological activity. The method is based on the one-step conversion of poly(acrylic anhydride) (pAAn) to linear polymers presenting multiple units of R on side chains, pAA(R): the polymers are obtained by ultrasonication of a suspension of pAAn and aqueous RNH2 contained in a 250-mu L well of a microtiter plate. Using this method, derivatives of pAA having N-acetylneuraminic acid (NeuAc-L-NH2) as a side chain, pAA(NeuAc-L), were generated and assayed for ability to inhibit hemagglutination (HAI) of chicken erythrocytes by influenza virus A (X-31); the constant (KHAT) describing this inhibition is calculated on the basis of the concentration of NeuAc groups in solution, rather than the concentration of polymer molecules. Go-polymeric pAA(NeuAc-L-n; L-n=different linking groups) with a range of mole fractions of NeuAc-L-NH2 (chi(NeuAc-L)=0.02-0.11) exhibited HAI activities with K-i(HAI) values between 27 and 0.30 mu M. Using combinations of NeuAc-L-NH2 and one of 26 different primary amines RNH2, a variety of ter-polymeric pAA(NeuAc-L; R) (chi(Neu-Ac-L)similar to 0.05; chi(R) similar to 0.06) were also generated and assayed. Certain ter-polymers yielded values of K-i(HAI) that were lower by a factor of similar to 10(4) than that of the parent co-polymeric pAA(NeuAc-L): the most active inhibitor was pAA(NeuAc-L; L-3-(2'-naphthyl)alanine)) (K(i)(HAI)approximate to 0.05 mM). Typically, the incorporation of hydrophobic-especially aromatic-side chains enhanced activities. These polymers (pAA(NeuAc-L; R)) belong to a new class of polymeric, polyvalent sialosides that are potent inhibitors of the adsorption of influenza virus to erythrocytes. They were active with only low to moderate levels of incorporation of functional groups into the side chains: chi(NeuAc-L)similar to 0.05; chi(R) similar to 0.06.

  DOI：

  10.1021/ja963519x
• 作为产物：
  描述：

  丹酰氯 、 N6-Cbz-L-赖氨酸 在 碳酸氢钠 作用下， 以 水 、 丙酮 为溶剂， 反应 2.0h， 生成 N^ε-benzyloxycarbonyl-N^α-dansyl-L-lysine
  参考文献：
  名称：

  Determination of enantiomeric purity of commercial 14C- and 3H-labeled L-α-amino acids

  摘要：

  DOI：

  10.1002/(sici)1099-1344(199806)41:6<477::aid-jlcr104>3.0.co;2-3

文献信息

• Dansyl-modified β-cyclodextrin with a monensin residue as a hydrophobic, metal responsive cap
  作者：Michiei Nakamura、Akira Ikeda、Nobuyuki Ise、Tsukasa Ikeda、Hiroshi Ikeda、Fujio Toda、Akihiko Ueno

  DOI：10.1039/c39950000721

  日期：——

  The guest-binding abilities of the monensin–dansyl–β-cyclodextrin triad system 3 are enhanced by the presence of the hydrophobic monensin residue as well as by sodium ions which may interact with monensin.

  由于疏水性莫能菌素残基的存在以及可能与莫能菌素发生反应的钠离子，莫能菌素-丹酰-β-环糊精三联体系3的客体结合能力得到增强。
• Fluorescent Cyclodextrins Responsive to Molecules and Metal Ions. Fluorescence Properties and Inclusion Phenomena of <i>N</i>^α-Dansyl-<scp>l</scp>-lysine-β-cyclodextrin and Monensin-Incorporated <i>N</i>^α-Dansyl-<scp>l</scp>-lysine-β-cyclodextrin
  作者：Akihiko Ueno、Akira Ikeda、Hiroshi Ikeda、Tsukasa Ikeda、Fujio Toda

  DOI：10.1021/jo9807870

  日期：1999.1.1

  N-alpha-Dansyl-L-lysine-beta-cyclodextrin with a monensin unit (1) was prepared as a fluorescent chemosensor for molecule recognition. Its fluorescence properties and inclusion phenomena were examined using N-alpha-dansyl-L-lysine-beta-cyclodextrin (2) and N-epsilon-benzyloxycarbonyl-N-alpha-dansyl-L-lysine-beta-cyclodextrin (3) as reference compounds. The fluorescence peak intensities of these hosts are in the order 2 > 1 > 3, suggesting that the dansyl unit of 2 is most deeply included in the beta-cyclodextrin cavity. The host 1 exhibits two Lifetimes, both in the absence of a lest [18.2 ns (81.8%) and 10.9 ns (18.2%)] and in the presence of 1-adamantanol(0.3 mM) [16.3 ns (17.8%) and 9.4 ns (82.2%)], demonstrating that 1 exists predominantly as a self-inclusion form with a longer lifetime and that it excludes the dansyl moiety to outside the cavity upon guest accommodation. A sodium cation in a solution of 1 enhanced the binding ability of 1 and increased the guest-dependent fluorescence variation. All of these results demonstrate that the monensin moiety of I is effective in changing the environment around the cyclodextrin cavity by forming a ring-like conformation with a sodium ion in the center.
• Determination of enantiomeric purity of commercial 14C- and 3H-labeled L-α-amino acids
  作者：Joseph W. Lefevre、Neil J. Bonzagni、Lara L. Chappell、David J. Clement、Jeb R. Albro、Denise M. Lezynski

  DOI：10.1002/(sici)1099-1344(199806)41:6<477::aid-jlcr104>3.0.co;2-3

  日期：1998.6
• Generation and <i>in Situ</i> Evaluation of Libraries of Poly(acrylic acid) Presenting Sialosides as Side Chains as Polyvalent Inhibitors of Influenza-Mediated Hemagglutination
  作者：Seok-Ki Choi、Mathai Mammen、George M. Whitesides

  DOI：10.1021/ja963519x

  日期：1997.5.1

  This paper describes a simple, microscale method for generating and evaluating libraries of derivatives of poly(acrylic acid) (pAA) that present mixtures of side chains that influence their biological activity. The method is based on the one-step conversion of poly(acrylic anhydride) (pAAn) to linear polymers presenting multiple units of R on side chains, pAA(R): the polymers are obtained by ultrasonication of a suspension of pAAn and aqueous RNH2 contained in a 250-mu L well of a microtiter plate. Using this method, derivatives of pAA having N-acetylneuraminic acid (NeuAc-L-NH2) as a side chain, pAA(NeuAc-L), were generated and assayed for ability to inhibit hemagglutination (HAI) of chicken erythrocytes by influenza virus A (X-31); the constant (KHAT) describing this inhibition is calculated on the basis of the concentration of NeuAc groups in solution, rather than the concentration of polymer molecules. Go-polymeric pAA(NeuAc-L-n; L-n=different linking groups) with a range of mole fractions of NeuAc-L-NH2 (chi(NeuAc-L)=0.02-0.11) exhibited HAI activities with K-i(HAI) values between 27 and 0.30 mu M. Using combinations of NeuAc-L-NH2 and one of 26 different primary amines RNH2, a variety of ter-polymeric pAA(NeuAc-L; R) (chi(Neu-Ac-L)similar to 0.05; chi(R) similar to 0.06) were also generated and assayed. Certain ter-polymers yielded values of K-i(HAI) that were lower by a factor of similar to 10(4) than that of the parent co-polymeric pAA(NeuAc-L): the most active inhibitor was pAA(NeuAc-L; L-3-(2'-naphthyl)alanine)) (K(i)(HAI)approximate to 0.05 mM). Typically, the incorporation of hydrophobic-especially aromatic-side chains enhanced activities. These polymers (pAA(NeuAc-L; R)) belong to a new class of polymeric, polyvalent sialosides that are potent inhibitors of the adsorption of influenza virus to erythrocytes. They were active with only low to moderate levels of incorporation of functional groups into the side chains: chi(NeuAc-L)similar to 0.05; chi(R) similar to 0.06.