酶催化合成胺和手性胺衍生物及其聚合物的研究
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摘要
胺类化合物是有机化学中的一类重要的化合物,常用作医药、香料和有机合成工业的重要中间体。本论文主要发展了有机介质中的酶催化方法,合成制备了一系列可聚合的胺类衍生物及其含糖的胺类衍生物,同时对这些含糖衍生物的两亲性质进行了研究；对胺类化合物进行酶催化可控动力学拆分研究,制备了可聚合的手性胺类药物衍生物；以及合成了含手性胺的均聚物及其含糖的胺类共聚物,并对这些聚合物的缓释性能进行了考察研究。
论文发展了非水介质中酶催化合成胺类衍生物的方法。以伯胺类化合物(美西律、1-甲基-3-苯基丙胺和1-苯乙胺)和仲胺类化合物(美托洛尔、比索洛尔和倍他洛尔)为底物,以具有不同链长的直链脂肪族二酸二乙烯酯(C4、C6、C9和C10)为酰化试剂,通过酶和有机溶剂的调控合成了12种新型的可聚合的胺类乙烯酯；并以仲胺类化合物(美托洛尔、比索洛尔和倍他洛尔)的乙烯酯为研究底物,与不同的单糖(葡萄糖、半乳糖和甘露糖)和二糖(蔗糖和麦芽糖)反应,在有机介质中酶催化条件下合成了6种含糖的仲胺类衍生物；并对酰化试剂、底物结构与含糖的仲胺类衍生物的溶解性关系进行了考察研究。
论文研究了美西律及其同系物的8种胺类衍生物对映体的分离方法,主要考察了不同的手性柱(Chiralcel OD-H和Chiralcel OJ-H).流动相比例和底物结构对对映体分离的影响,以及采用旋光检测器及圆二色检测器研究这些样品洗脱的先后顺序等。研究结果表明当流动相中正已烷和异丙醇体积比分别为90/10、80/20和70/30时,其中的7种化合物能够在Chiralcel OD-H柱上获得对映体分离；而当正已烷和异丙醇体积比为90/10时,5种化合物能够在Chiralcel OJ-H柱上获得对映体分离；而当正已烷和异丙醇体积比为80/20和70/30时,这8种化合物在Chiralcel OJ-H柱上仅获得部分分离。采用旋光检测器和圆二色谱检测器进行检测表明：旋光度为正的R型结构先洗脱出来,随后洗脱出来的是S构型。
论文研究了采用不同的酰基供体对美托洛尔进行不可逆动力学拆分,得到光学纯度较高的可聚合S-美托洛尔乙烯酯。以美西律乙烯酯为研究底物,分别以CAL-B和lipozyme(?)为催化剂,在THF-PBS (pH=7.0,90/10, v/v)和甲苯中反应,可控性的得到高光学纯度(e.e.>93%)的可聚合R-N-(5-乙烯酯戊酰)美西律和S-N-(5-乙烯酯戊酰)美西律,考察了底物结构、混合溶剂、磷酸盐的pH、混合溶剂的比例等条件对反应的影响；同时由于反应的位点距离手性中心为八个碳原子,故反应为远程反应。
论文研究制备了一系列含美托洛尔、美西律和手性美西律药物的均聚物及其含糖共聚物,考察优化了影响聚合反应的因素,且产物经IR、NMR和GPC等手段表征分析。研究了外消旋及手性美西律均聚物和共聚物在pH为7.4的磷酸盐缓冲溶液条件下的体外释放性能,研究结果表明含糖共聚物高分子前药的释放明显快于药物乙烯酯的均聚物,且在酸性条件下更有利于释放。
Amines are important compounds because of their broad range of applications and their pharmacological properties. In this thesis, enzymatic synthesis of a series of polymerizable amine derivatives and amine-saccharide conjugates, and the water-solubility of drug-saccharide conjugates were also investigated, controlled enzymatic reaction, preparation of polymeric chiral compounds with saccharides, and investigation of amine derivatives and their polymers were developed.
The enzymatic synthesis of amine derivatives in non-aqueous media was developed. Primary amines (mexiletine, 1-methyl-3-phenylpropylamine and 1-phenylethylamine) and secondary amines (metoprolol, bisoprolol and betaxolol) were chosen as substrates, divinyl dicarboxylates with different carbon length were used as acylating agents. Twelve kinds of new polymerizable N-(vinyloxycarbonyl)-amine were prepared in better yields through screening enzymes and solvents in enzyme-catalyzed reaction.
Highly selective enzymatic acylation of N-(vinyloxycarbonyl)-secondary amines (metoprolol, bisoprolol and betaxolol) with different monosaccharides (glucose, galactose and mannose) and disaccharides (maltose and sucrose) were developed to prepare six kinds of new amine-saccharide conjugates, which showed better water-solubility. The reaction conditions, such as acylating agents, structures of substrates, and the water-solubility of amine-saccharide conjugates were also investigated, the results suggested that amine-saccharide conjugates can be considered as a promising prodrug form.
A series of novel designed mexiletine derivatives and its analogues were prepared, the enantioseparations were performed on polysaccharide-based chiral stationary phase, Chiralcel OD-H column and Chiralcel OJ-H column, under normal-phase mode. The effects of the concentration of isopropanol in the mobile phase and the structures of the samples on enantioseparation, and the elution order of the enantiomers using optical rotation (OR) and circular dichroism (CD) detector were studied. It was resulted that when the ratio of n-hexane to isopropanol was 90/10,80/20 and 70/30 (v/v), seven of the eight enantiomers got baseline separation on Chiralcel OD-H column. When the ratio of n-hexane to isopropanol was 90/10 (v/v), five enantiomers got successfully separation on Chiralcel OJ-H column. When the ratio of n-hexane to isopropanol was 80/20 and 70/30 (v/v), the eight enantiomers were all partial revolved on Chiralcel OJ-H column. Moreover, at the same conditions of that the ratio of n-hexane to isopropanol was 90/10 (v/v), sample h was a single peak when it was separated on Chiralcel OD-H column, while it was successful separated on Chiralcel OJ-H column. The effects of structural features were also discussed. Using a CD detector and an OR detector, it showed that R-enantiomer appears before S-enantiomer separated on both Chiralcel OJ-H and OD-H column.
The resolution of metoprolol was investigated by enzyme-catalyzed reaction with different donors. The good e.e. value and low yield of N-(5-vinyloxycarbonylpentanoyl) metoprolol was obtained. When N-(5-vinyloxycarbonylpentanoyl)mexiletine was chosen as substrate, the polymeriable R-and S-enantiomers of N-(5-vinyloxy carbonylpentanoyl)mexiletine were obtained through optimization the influences of reaction conditions (such as co-solvents, pH of PBS and ratio of co-solvents, etc). Lipozyme(?) provided polymerizable S-enantiomer in 93% e.e. in toluene. The R-enantiomer could be obtained in>98% e.e. by CAL-B in THF-PBS (pH=7.0,90/10, v/v). The addition of PBS could improve the stereoselectivity of CAL-B by 15-fold than that in pure THF. Moreover, the influences of the structures of amines on the reaction were also discussed. The hydrolysis position was occurred at the terminal ester bond, it was eight atoms away from the stereocenter, and it was indicated the reaction was a remote reaction.
The chemo-enzymatic method for the preparation of polymeric compounds of metoprolol, mexiletine and chiral mexiletine using AIBN as initiator was developed. The products were obtained and characterized by IR, NMR and GPC. A series of homopolymer and copolymers containing drugs and glucose monomers had high molecular weight. The in-vitro release of homopolymer and copolymers with glucose of mexiletine was investigated in pH=7.4 buffer solution. The results showed that the release rate of copolymer was faster than that of homopolymer, and copolymeric amine derivatives were favor in acid condition in-vitro release.
论文发展了非水介质中酶催化合成胺类衍生物的方法。以伯胺类化合物(美西律、1-甲基-3-苯基丙胺和1-苯乙胺)和仲胺类化合物(美托洛尔、比索洛尔和倍他洛尔)为底物,以具有不同链长的直链脂肪族二酸二乙烯酯(C4、C6、C9和C10)为酰化试剂,通过酶和有机溶剂的调控合成了12种新型的可聚合的胺类乙烯酯；并以仲胺类化合物(美托洛尔、比索洛尔和倍他洛尔)的乙烯酯为研究底物,与不同的单糖(葡萄糖、半乳糖和甘露糖)和二糖(蔗糖和麦芽糖)反应,在有机介质中酶催化条件下合成了6种含糖的仲胺类衍生物；并对酰化试剂、底物结构与含糖的仲胺类衍生物的溶解性关系进行了考察研究。
论文研究了美西律及其同系物的8种胺类衍生物对映体的分离方法,主要考察了不同的手性柱(Chiralcel OD-H和Chiralcel OJ-H).流动相比例和底物结构对对映体分离的影响,以及采用旋光检测器及圆二色检测器研究这些样品洗脱的先后顺序等。研究结果表明当流动相中正已烷和异丙醇体积比分别为90/10、80/20和70/30时,其中的7种化合物能够在Chiralcel OD-H柱上获得对映体分离；而当正已烷和异丙醇体积比为90/10时,5种化合物能够在Chiralcel OJ-H柱上获得对映体分离；而当正已烷和异丙醇体积比为80/20和70/30时,这8种化合物在Chiralcel OJ-H柱上仅获得部分分离。采用旋光检测器和圆二色谱检测器进行检测表明：旋光度为正的R型结构先洗脱出来,随后洗脱出来的是S构型。
论文研究了采用不同的酰基供体对美托洛尔进行不可逆动力学拆分,得到光学纯度较高的可聚合S-美托洛尔乙烯酯。以美西律乙烯酯为研究底物,分别以CAL-B和lipozyme(?)为催化剂,在THF-PBS (pH=7.0,90/10, v/v)和甲苯中反应,可控性的得到高光学纯度(e.e.>93%)的可聚合R-N-(5-乙烯酯戊酰)美西律和S-N-(5-乙烯酯戊酰)美西律,考察了底物结构、混合溶剂、磷酸盐的pH、混合溶剂的比例等条件对反应的影响；同时由于反应的位点距离手性中心为八个碳原子,故反应为远程反应。
论文研究制备了一系列含美托洛尔、美西律和手性美西律药物的均聚物及其含糖共聚物,考察优化了影响聚合反应的因素,且产物经IR、NMR和GPC等手段表征分析。研究了外消旋及手性美西律均聚物和共聚物在pH为7.4的磷酸盐缓冲溶液条件下的体外释放性能,研究结果表明含糖共聚物高分子前药的释放明显快于药物乙烯酯的均聚物,且在酸性条件下更有利于释放。
Amines are important compounds because of their broad range of applications and their pharmacological properties. In this thesis, enzymatic synthesis of a series of polymerizable amine derivatives and amine-saccharide conjugates, and the water-solubility of drug-saccharide conjugates were also investigated, controlled enzymatic reaction, preparation of polymeric chiral compounds with saccharides, and investigation of amine derivatives and their polymers were developed.
The enzymatic synthesis of amine derivatives in non-aqueous media was developed. Primary amines (mexiletine, 1-methyl-3-phenylpropylamine and 1-phenylethylamine) and secondary amines (metoprolol, bisoprolol and betaxolol) were chosen as substrates, divinyl dicarboxylates with different carbon length were used as acylating agents. Twelve kinds of new polymerizable N-(vinyloxycarbonyl)-amine were prepared in better yields through screening enzymes and solvents in enzyme-catalyzed reaction.
Highly selective enzymatic acylation of N-(vinyloxycarbonyl)-secondary amines (metoprolol, bisoprolol and betaxolol) with different monosaccharides (glucose, galactose and mannose) and disaccharides (maltose and sucrose) were developed to prepare six kinds of new amine-saccharide conjugates, which showed better water-solubility. The reaction conditions, such as acylating agents, structures of substrates, and the water-solubility of amine-saccharide conjugates were also investigated, the results suggested that amine-saccharide conjugates can be considered as a promising prodrug form.
A series of novel designed mexiletine derivatives and its analogues were prepared, the enantioseparations were performed on polysaccharide-based chiral stationary phase, Chiralcel OD-H column and Chiralcel OJ-H column, under normal-phase mode. The effects of the concentration of isopropanol in the mobile phase and the structures of the samples on enantioseparation, and the elution order of the enantiomers using optical rotation (OR) and circular dichroism (CD) detector were studied. It was resulted that when the ratio of n-hexane to isopropanol was 90/10,80/20 and 70/30 (v/v), seven of the eight enantiomers got baseline separation on Chiralcel OD-H column. When the ratio of n-hexane to isopropanol was 90/10 (v/v), five enantiomers got successfully separation on Chiralcel OJ-H column. When the ratio of n-hexane to isopropanol was 80/20 and 70/30 (v/v), the eight enantiomers were all partial revolved on Chiralcel OJ-H column. Moreover, at the same conditions of that the ratio of n-hexane to isopropanol was 90/10 (v/v), sample h was a single peak when it was separated on Chiralcel OD-H column, while it was successful separated on Chiralcel OJ-H column. The effects of structural features were also discussed. Using a CD detector and an OR detector, it showed that R-enantiomer appears before S-enantiomer separated on both Chiralcel OJ-H and OD-H column.
The resolution of metoprolol was investigated by enzyme-catalyzed reaction with different donors. The good e.e. value and low yield of N-(5-vinyloxycarbonylpentanoyl) metoprolol was obtained. When N-(5-vinyloxycarbonylpentanoyl)mexiletine was chosen as substrate, the polymeriable R-and S-enantiomers of N-(5-vinyloxy carbonylpentanoyl)mexiletine were obtained through optimization the influences of reaction conditions (such as co-solvents, pH of PBS and ratio of co-solvents, etc). Lipozyme(?) provided polymerizable S-enantiomer in 93% e.e. in toluene. The R-enantiomer could be obtained in>98% e.e. by CAL-B in THF-PBS (pH=7.0,90/10, v/v). The addition of PBS could improve the stereoselectivity of CAL-B by 15-fold than that in pure THF. Moreover, the influences of the structures of amines on the reaction were also discussed. The hydrolysis position was occurred at the terminal ester bond, it was eight atoms away from the stereocenter, and it was indicated the reaction was a remote reaction.
The chemo-enzymatic method for the preparation of polymeric compounds of metoprolol, mexiletine and chiral mexiletine using AIBN as initiator was developed. The products were obtained and characterized by IR, NMR and GPC. A series of homopolymer and copolymers containing drugs and glucose monomers had high molecular weight. The in-vitro release of homopolymer and copolymers with glucose of mexiletine was investigated in pH=7.4 buffer solution. The results showed that the release rate of copolymer was faster than that of homopolymer, and copolymeric amine derivatives were favor in acid condition in-vitro release.
引文
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