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| 研究生： |
陳建宏 Chen, Chien-Hong |
|---|---|
| 論文名稱： |
鎳/鐵氫化酵素和鐵醯腈水解酵素活化中心之小分子模型化合物研究 Small Molecule Models of [NiFe] Hydrogenase and Fe-Containing Nitrile Hydratase Active-Sites |
| 指導教授： |
廖文峯
Liaw, Wen-Feng |
| 口試委員: | |
| 學位類別： |
博士 Doctor |
| 系所名稱： |
理學院 - 化學系 Department of Chemistry |
| 論文出版年： | 2005 |
| 畢業學年度： | 93 |
| 語文別： | 英文 |
| 論文頁數： | 152 |
| 中文關鍵詞： | 氫化酵素 、水解酵素 、金屬酵素 、配位化學 、一氧化氮 |
| 外文關鍵詞： | hydrogenase, nitrile hydratase, metalloenzyme, coordination chemistry, nitric oxide |
| 相關次數： | 點閱：3 下載：0 |
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生化擬態之鎳(II)/(III)-硫化合物
一系列鎳(II)-硫醇化合物，[NiII(X)(P(o-C6H4S)2(o-C6H4SH))]- (X = Se-p-C6H4-Cl (1), 2-S-C4H3S (2), Cl (9))和[NiII(PPh3)(P(o-C6H4S)2(o-C6H4SH))] (5a)/(5b)已經成功的合成出來。這些平面四方形結構的化合物具有一個硫醇官能基，硫醇官能基上的質子同時和分子內的硫原子與鎳原子產生交互作用，並且穩定此類分子的存在。藉由紅外線光譜學、核磁共振光譜及單晶X光繞射結構解析的研究，確實證明此特殊分子內作用力的存在。由氘同位素水分子與硫醇官能基上氫質子的交換實驗，配合紅外線光譜學、核磁共振光譜，亦證明硫醇官能基上氫質子的存在。分析此類化合物的紅外線光譜，我們發現此種特殊的分子內作用力其強弱與鎳原子上的電子密度相關。當鎳原子上的電子密度愈高時，此特殊的分子內作用力愈強，並且導致硫醇官能基上的質子更酸性化。此酸性化的結果使得此類硫醇化合物容易被氧化成鎳(III)-硫化合物。將化合物1，2，5a和5b與氧氣反應分別得到鎳(III)-硫化合物 3 、4及6 ([NiIII(X)(P(o-C6H4S)3)]- (X = Se-p-C6H4-Cl (3), 2-S-C4H3S (4)； [NiIII(PPh3)(P(o-C6H4S)3)] (6))。這些鎳(III)-硫化合物皆為雙三角錐的結構，並且經由電子順磁光譜證實皆具有一個電子在dz2軌域上。在環電位儀上，鎳(III)-硫化合物 3、4在-1.17 V；鎳(III)-硫化合物 6在-0.865 V，顯示出由鎳(III)接受電子還原成鎳(II)的現象。藉由另一個鎳(II)-硫醚化合物10 ([NiII(PPh3)(P(o-C6H4S)2(o-C6H4-SCH3))])的單晶X光結構繞射解析，也更加證實鎳(II)-硫醇化合物上質子確實是受到同分子內的硫原子與鎳原子同時吸引，才會座落在鎳原子與硫醇官能基的硫原子之間。
生化擬態之鐵(II)/(III)-硫-硝基化合物
一系列的五配位鐵-硫-硝基化合物([PPN][Fe(NO)(S,S-C6H2-3,6-Cl2)2] (13)、 [PPN]2[Fe2(NO)2(S,SO2-C6H2-3,6-Cl2)2(S,S-C6H2-3,6-Cl2)2] (14)、 [PPN]2[(NO)Fe(S,S-C6H2-3,6-Cl2)2] (15)、 [PPN]2[Fe(NO)(S,SO2-C6H2-3,6-Cl2)(S,S-C6H2-3,6-Cl2)] (16))已經合成成功，並且經過紅外線光譜、紫外線-可見光光譜、核磁共振光譜及單晶X光繞射解析鑑定。將化合物13與氧氣反應可以得到化合物14，此反應顯示有{Fe(NO)}6組成的化合物13具有引發硫配位基上硫原子氧化的能力。將化合物13以[EtS]-還原可以得到化合物15，此分子的Fe-N-O角度為153.4度，呈現彎曲的形式。以[EtS]-將化合物14還原可以得到化合物16，其分子的Fe-N-O角度為166.0度，彎曲度略小於化合物15。此外，在紫外線照射下，化合物14會轉變成化合物13，化合物16則會轉變成化合物15。由化合物13-14-16-15之間的轉變也許可以提供一些訊息，以解釋腈水解酵素在活化態與非活化態之間轉換的機制。
For the biomimetic nickel(II) thiolate-thiol and nickel (III)-thiolate complexes
A series of mononuclear, distorted square planar complexes [NiII(X)(P(o-C6H4S)2(o-C6H4SH))]- (X = Se-p-C6H4-Cl (1), 2-S-C4H3S (2), Cl (9)) and [NiII(PPh3)(P(o-C6H4S)2(o-C6H4SH))] (5a)/(5b) with a S-H proton directly interacting with nickel atom or with both nickel and sulfur atoms were synthesized. The presence of intramolecular [Ni•••H-SR] interaction or combinations of intramolecular [Ni-S•••H-SR]/[Ni•••H-SR] interactions were verified in the solid state by the IR □SH stretching bands, the exo-thiol protons resonances of 1H NMR spectra and subsequently confirmed by single crystal X-ray diffraction studies. The exo-thiol proton in complexes 1, 2, and 5a was identified as a D2O exchangeable proton from NMR and IR studies. Based on the observations of IR νS-H stretching frequencies, the extent of interactions (exo-thiol interaction modes ([Ni-S…H-S], [Ni…H-S] or combinations)) was modulated by the electronic density surrounding nickel resulting from the distinct terminally-coordinated donor ligands [Se-p-C6H4-Cl]-, [SePh]-, [S-C4H3S]-, [Cl]-, and PPh3 in these NiII-exo-thiol complexes 1, 2, 5a, 5b, 8, and 9. Instead of the ligand-based oxidation to form dinuclear Ni(II) complexes and dichalcogenide, oxidation of THF-CH3CN solution of complexes 1 and 2 by O2 resulted in the formation of the mononuclear, distorted trigonal bipyramidal [NiIII(X)(P(o-C6H4S)3)]- (X = Se-p-C6H4-Cl (3), 2-S-C4H3S (4)) accompanied by byproduct H2O identified by 1H NMR. Also, the reaction of dry O2 with THF solution of complex 5a/5b afforded the mononuclear, distorted trigonal bipyramidal [NiIII(PPh3)(P(o-C6H4S)3)] (6). Reduction of complex 6 or deprotonation of complex 5a/5b yielded [NiII(PPh3)(P(o-C6H4S)3)]- (7), which also displayed the distorted trigonal bipyramidal geometry. The EPR spectra of complexes 3 and 4 exhibiting high rhombicities with three principal g values of 2.30, 2.09 and 2.0 are consistent with Ni(III) with the odd electron in the dz2 orbital. Complexes 3, 4, and 6 undergoes a reversible NiIII/II process at E1/2 = -1.17 V in CH3CN (complexes 3 and 4) and -0.865 V (complex 6) in CH2Cl2 (vs Cp2Fe/Cp2Fe+), respectively. In addition, the single crystal X-ray diffraction studies of complex [NiII(PPh3)(P(o-C6H4S)2(o-C6H4-SCH3))] (10a/10b) give the evidence that the exo-thiol protons of the Ni(II) exo-thiol complexes 1, 2, 5a, 5b and 9 were attracted by nickel atom and sulfur atom of thiolate, resulting in the intramolecular interactions (combinations of [Ni-S…H-S]/[Ni…HS] or [Ni…HS]). Reaction of complex 10 with [SPh]- and [SePh]- led to the formation of [NiII(EPh)(P(o-C6H4S)2(o-C6H4-SCH3))]- (E = S (11); Se (12)). Combinations of 1H NMR spectra and single-crystal X-ray diffraction studies of mononuclear NiII exo-thioehter complexes 10a, 10b, 11, and 12 revealed that the intramolecular interaction between NiII and thioether sulfur atom became weaker when the temperature is increased or the more electron-donating terminal ligand is ligated to NiII center.
For the iron-thiolate nitrosyl complexes
The five-coordinated iron-thiolate nitrosyl complexes [PPN][Fe(NO)(S,S-C6H2-3,6-Cl2)2] (13), [PPN]2[Fe2(NO)2(S,SO2-C6H2-3,6-Cl2)2(S,S-C6H2-3,6-Cl2)2] (14), [PPN]2[(NO)Fe(S,S-C6H2-3,6-Cl2)2] (15), and [PPN]2[Fe(NO)(S,SO2-C6H2-3,6-Cl2)(S,S-C6H2-3,6-Cl2)] (16) have been isolated and characterized by IR, UV/vis, NMR spectra and X-ray crystallography. Upon contact with dry O2, iron-thiolate nitrosyl complex 13 containing {Fe(NO)}6 core trigger sulfur oxygenation to yield the S-bonded monosulfinate iron complex 14. Reduction of complex 13 by [EtS]- yields complex 15 with a bent Fe-N-O bond angle of 153.4□. Compared to the reaction of O2 with complex 13, there is to a certain extent an attack of O2 on the •NO radical of complex 15 containing {Fe(NO)}7 core leading to the formation of complex 13 accompanied by the minor products, [Fe(S,S-C6H4)2]22– and [NO3]–. Treatment of 1 equiv of [EtS]– and complex 14 in CH3CN-THF yields complex 16 along with (EtS)2 identified by 1H NMR. Compared to complex 15, complex 16 with the less electron-donating sulfinate ligand coordinated to {FeNO}7 core were oxidized by O2 to yield complex 14. Obviously, the electronic perturbation of the {Fe(NO)}7 core caused by the coordinated sulfinate in complex 16 may serve to regulate the reactivity of complex 16 toward O2. The iron-sulfinate nitrosyl species with {Fe(NO)}6/7 core exhibit the photolabilization of sulfur-bound [O] moiety under irradiation. The interconversion of complexes 13-14-16-15 may provide some clues to the transformation pathways between the active and inactive NO-bound forms of Fe-containing nitrile hydratase.
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