2-[2-(1-ethylenediamine-N,N',N'-trimethoxycarbonylmethylacetoamide-2-aminoethylcarbamoyl)ethyl]-18-propionic acid methyl ester-8,13-divinyl-3,7,12,17-tetramethylporphinatozinc(II) | 1097200-21-9

• 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: 2-[2-(1-ethylenediamine-N,N',N'-trimethoxycarbonylmethylacetoamide-2-aminoethylcarbamoyl)ethyl]-18-propionic acid methyl ester-8,13-divinyl-3,7,12,17-tetramethylporphinatozinc(II)
• CAS: 1097200-21-9
• 化学式: C₅₀H₆₀N₈O₁₀Zn
• 分子量: 998.464
• InChiKey: VIKUQVXUCPAYPR-AQCKCKBCSA-L

计算性质

• 辛醇/水分配系数(LogP)：
  None
• 重原子数：
  None
• 可旋转键数：
  None
• 环数：
  None
• sp3杂化的碳原子比例：
  None
• 拓扑面积：
  None
• 氢给体数：
  None
• 氢受体数：
  None

反应信息

• 作为反应物：
  描述：

  2-[2-(1-ethylenediamine-N,N',N'-trimethoxycarbonylmethylacetoamide-2-aminoethylcarbamoyl)ethyl]-18-propionic acid methyl ester-8,13-divinyl-3,7,12,17-tetramethylporphinatozinc(II) 、 zinc(II) acetate dihydrate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 以79%的产率得到2-[2-(1-ethylenediamine-N,N',N'-tricarboxymethylacetoamide-2-aminoethylcarbamoyl)ethyl]-18-propionic acid-8,13-divinyl-3,7,12,17-tetramethylporphinatozinc(II)
  参考文献：
  名称：

  Metal Ion-Dependent Fluorescent Dynamics of Photoexcited Zinc−Porphyrin and Zinc−Myoglobin Modified with Ethylenediaminetetraacetic Acid

  摘要：

  The reconstituted zinc - myoglobin (ZnMb) dyads, ZnMb-[M-II(edta)], have been prepared by incorporating a zinc-porphyrin (ZnP) cofactor modified with ethylenediaminetetraacetic acid (H(4)edta) into apo-Mb. In case of the monomeric ZnP(edta) cofactor coordinated by one pyridine molecule, ZnP(py)(edta), a spontaneous 1: 1 complex with a transient metal ion was formed in an aqueous solvent, and the photoexcited singlet state of ZnP, (1)(ZnP)*, was quenched by the [Cu-II(edta)] moiety through intramolecular photoinduced electrontransfer (ET) reaction. The rate constant for the intramolecular quenching ET (k(q)) at 25 degrees C was successfully obtained as k(q) = 5.1 x 10(9) s(-1). In the case of Co2+, Ni2+, and Mn2+, intersystem crossing by paramagnetic effect was mainly considered between (1)(ZnP)* and the [M-II(edta)] complex. For the ZnMb-[M-II(edta)] systems, the intramolecular ET reaction between the excited singlet state of (I)(ZnMb)* and the [Cu-II(edta)] moieties provided the slower quenching rate constant, k(q) = 2.1 x 10(8) s(-1), compared with that of the ZnP(py)(edta) one. Kinetic studies also presented the efficient fluorescence quenching of the (1)(ZnMb)*-[Co-II(edta)] dyad. Our study clearly demonstrates that wrapping of the ZnP cofactor by the apoprotein matrix and synthetic manipulation at the Mb surface ensure metal ion-sensitive fluorescent dynamics of ZnMb and provides valuable information to elucidate the complicated mechanism of the biological photoinduced ET reactions of hemoproteins.

  DOI：

  10.1021/jp807692w
• 作为产物：
  描述：

  8,11-divinyl-3,7,12,17-tetramethylporphine-2-[2-(1-ethylenediamine-N,N',N'-trimethoxycarbonylmethylacetoamide-2-aminoethylcarbamoyl)ethyl]-18-propionic acid methyl ester 、 zinc(II) acetate dihydrate 以 甲醇 、 二氯甲烷 为溶剂， 以60%的产率得到2-[2-(1-ethylenediamine-N,N',N'-trimethoxycarbonylmethylacetoamide-2-aminoethylcarbamoyl)ethyl]-18-propionic acid methyl ester-8,13-divinyl-3,7,12,17-tetramethylporphinatozinc(II)
  参考文献：
  名称：

  Metal Ion-Dependent Fluorescent Dynamics of Photoexcited Zinc−Porphyrin and Zinc−Myoglobin Modified with Ethylenediaminetetraacetic Acid

  摘要：

  The reconstituted zinc - myoglobin (ZnMb) dyads, ZnMb-[M-II(edta)], have been prepared by incorporating a zinc-porphyrin (ZnP) cofactor modified with ethylenediaminetetraacetic acid (H(4)edta) into apo-Mb. In case of the monomeric ZnP(edta) cofactor coordinated by one pyridine molecule, ZnP(py)(edta), a spontaneous 1: 1 complex with a transient metal ion was formed in an aqueous solvent, and the photoexcited singlet state of ZnP, (1)(ZnP)*, was quenched by the [Cu-II(edta)] moiety through intramolecular photoinduced electrontransfer (ET) reaction. The rate constant for the intramolecular quenching ET (k(q)) at 25 degrees C was successfully obtained as k(q) = 5.1 x 10(9) s(-1). In the case of Co2+, Ni2+, and Mn2+, intersystem crossing by paramagnetic effect was mainly considered between (1)(ZnP)* and the [M-II(edta)] complex. For the ZnMb-[M-II(edta)] systems, the intramolecular ET reaction between the excited singlet state of (I)(ZnMb)* and the [Cu-II(edta)] moieties provided the slower quenching rate constant, k(q) = 2.1 x 10(8) s(-1), compared with that of the ZnP(py)(edta) one. Kinetic studies also presented the efficient fluorescence quenching of the (1)(ZnMb)*-[Co-II(edta)] dyad. Our study clearly demonstrates that wrapping of the ZnP cofactor by the apoprotein matrix and synthetic manipulation at the Mb surface ensure metal ion-sensitive fluorescent dynamics of ZnMb and provides valuable information to elucidate the complicated mechanism of the biological photoinduced ET reactions of hemoproteins.

  DOI：

  10.1021/jp807692w