有机胍盐催化吗啉二酮活性及立构专一性开环聚合研究
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摘要
随着高分子科学的发展和研究工作的深入,α-羟基酸与α-氨基酸的共聚物(Polydepsipeptides)颇受生物医用高分子科学领域科研工作者的重视。Polydepsipeptides兼具聚酯类高分子和聚氨基酸类高分子材料的优点,同时又具有较聚酯类高分子更好的亲水性和细胞黏附性,以及较聚氨基酸类高分子更好的溶解性和可加工性等。Polydepsipeptides在生物医学领域有着广阔的应用前景,例如可用作药物控释体系的载体、细胞生长载体、医用缝合线、医用敷料等。
本论文中所报道的创新性研究工作主要是关于通过仿生型无毒无金属有机胍盐催化剂催化吗啉-2,5-二酮的开环聚合反应制备乳酸与丝氨酸、乳酸与谷氨酸的共聚物,具体内容分述如下：
(1)通过醋酸肌酐胍催化的L-丙交酯与(3S)-苄氧甲基-(6S)-甲基-吗啉-2,5-二酮活性及立构专一性开环共聚合反应,合成出具有可控组成、高立构等规度的共聚物,后经脱保护反应获得具有生物可降解性和生物安全性的聚(L-乳酸-co-L-丝氨酸)。
(2)通过双环胍(1,5,7-三氮杂双环[4.4.0]-癸-5-烯,TBD)分别与乙醇酸、乳酸反应合成出两种新型仿生型无毒无金属有机胍盐催化剂——乙醇酸双环胍(TBDG)和乳酸双环胍(TBDL)。
(3)由起始原料L-谷氨酸经三步有机反应制备出一种新化合物——3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮(BCEMD)。
(4)通过乙醇酸双环胍催化的3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮的开环均聚合反应,合成出均聚物PBCEMD,后经脱保护反应获得具有生物可降解性和生物安全性的聚(乳酸-alt-谷氨酸)；通过开环聚合反应的动力学实验证明了该聚合反应具有活性聚合反应的特征；通过终止剂添加实验和大分子活性物种表征实验证明了该聚合反应的反应机理应为配位—插入机理。
(5)通过乙醇酸双环胍催化的DL-丙交酯与3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮开环共聚合反应,合成出具有可控组成及结构的共聚物,后经脱保护反应获得具有生物可降解性和生物安全性的聚(乳酸-co-谷氨酸)。
(6)通过乙醇酸双环胍或乳酸双环胍催化的丙交酯与3-苄氧甲基-6-甲基-吗啉-2,5-二酮开环共聚合反应,分别合成出具有可控组成及结构的共聚物,后经脱保护反应获得具有生物可降解性和生物安全性的聚(DL-乳酸-co-L-丝氨酸)和聚(L-乳酸-co-L-丝氨酸)。
(7)基于相关实验数据对比并讨论了：①3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮(BCEMD)与(3S)-苄氧甲基-(6RS)-甲基-吗啉-2,5-二酮的单体活性[(3S，6RS)-BMMD];②乙醇酸双环胍(TBDG)和乳酸双环胍(TBDL)的催化剂活性；③聚合反应温度的选取问题。
With the development of polymer science and the deepening of research works, copolymers of a-hydroxy acid and a-amino acid (polydepsipeptides) are greatly valued by scientists and researchers in the field of biomedical polymer science. Polydepsipeptides have the advantages of both polyesters and polyamino acids, and simultaneously they also have better hydrophilicity and cell adhesion than polyesters do, have better solubility and processability than polyamino acids do, etc. Polydepsipeptides possess broad application prospects in the biomedical field, such as that they can be used as carriers for controlled release drug delivery systems, cell growth vectors, surgical sutures, medical dressings and so on.
The innovative research works reported in this dissertation are mainly about preparation of copolymers of lactic acid and serine or copolymers of lactic acid and glumatic acid via Ring-Opening Polymerization of morpholine-2,5-diones catalyzed by biomimetic non-toxic metal-free organic guanidium salt catalysts. The specific contents are described as follows:
(1) Copolymers with controllable composition and high isotacticity were synthesized via the living and stereospecific ring-opening copolymerization of L-lactide and (3S)-benzyloxymethyl-(6S)-methyl-morpholine-2,5-dione catalyzed by creatinine acetate, and via deprotection reactions the biodegradable and bio-safe poly(L-lactic acid-co-L-serine)s were obtained then.
(2) Two new type biomimetic non-toxic metal-free organic guanidium salt catalysts bicyclic guanidium glycolate (TBDG) and bicyclic guanidium lactate (TBDL) were synthesized via the reaction of bicyclic guanidine (1,5,7-triaza-bicyclo-[4.4.0]-dec-5-ene, TBD) and glycolic acid or lactic acid respectively.
(3) A new compound3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione (BCEMD) was synthesized from the starting material L-glumatic acid via three-step organic reaction.
(4) Homopolymers PBCEMDs were synthesized via the ring-opening homopolymerization of3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione catalyzed by bicyclic guanidium glycolate, and via deprotection reactions the biodegradable and bio-safe poly(lactic acid-alt-glutamic acid)s were obtained then; It was proved that the polymerization possessed characteristics of living polymerization via kinetic experiments for the polymerization; It was certified that the mechanism of the polymerization should be coordination-insertion mechanism via the experiments of adding terminate agents and the characterization of macromolecular active species.
(5) Copolymers with controllable composition and structure were synthesized via the ring-opening copolymerization of DL-lactide and3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione catalyzed by bicyclic guanidium glycolate, and via deprotection reactions the biodegradable and bio-safe poly(lactic acid-co-glutamic acid)s were obtained then.
(6) Copolymers with controllable composition and structure were synthesized via the ring-opening copolymerization of lactide and3-benzyloxymethyl-6-methyl-morpholine-2,5-dione catalyzed by bicyclic guanidium glycolate or bicyclic guanidium lactate respectively, and via deprotection reactions the biodegradable and bio-safe poly(DL-lactic acid-co-L-serine)s and poly(L-lactic acid-co-L-serine)s were obtained then.
(7) Make some comparisons and discussions based on the related experimental data:①the monomer activities of3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione (BCEMD) and (3S)-benzyloxymethyl-(6RS)-methyl-morpholine-2,5-dione [(3S,6RS)-BMMD];②the catalyst activities of bicyclic guanidium glycolate (TBDG) and bicyclic guanidium lactate (TBDL);③the problem of selecting the temperature of copolymeriztions.
本论文中所报道的创新性研究工作主要是关于通过仿生型无毒无金属有机胍盐催化剂催化吗啉-2,5-二酮的开环聚合反应制备乳酸与丝氨酸、乳酸与谷氨酸的共聚物,具体内容分述如下：
(1)通过醋酸肌酐胍催化的L-丙交酯与(3S)-苄氧甲基-(6S)-甲基-吗啉-2,5-二酮活性及立构专一性开环共聚合反应,合成出具有可控组成、高立构等规度的共聚物,后经脱保护反应获得具有生物可降解性和生物安全性的聚(L-乳酸-co-L-丝氨酸)。
(2)通过双环胍(1,5,7-三氮杂双环[4.4.0]-癸-5-烯,TBD)分别与乙醇酸、乳酸反应合成出两种新型仿生型无毒无金属有机胍盐催化剂——乙醇酸双环胍(TBDG)和乳酸双环胍(TBDL)。
(3)由起始原料L-谷氨酸经三步有机反应制备出一种新化合物——3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮(BCEMD)。
(4)通过乙醇酸双环胍催化的3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮的开环均聚合反应,合成出均聚物PBCEMD,后经脱保护反应获得具有生物可降解性和生物安全性的聚(乳酸-alt-谷氨酸)；通过开环聚合反应的动力学实验证明了该聚合反应具有活性聚合反应的特征；通过终止剂添加实验和大分子活性物种表征实验证明了该聚合反应的反应机理应为配位—插入机理。
(5)通过乙醇酸双环胍催化的DL-丙交酯与3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮开环共聚合反应,合成出具有可控组成及结构的共聚物,后经脱保护反应获得具有生物可降解性和生物安全性的聚(乳酸-co-谷氨酸)。
(6)通过乙醇酸双环胍或乳酸双环胍催化的丙交酯与3-苄氧甲基-6-甲基-吗啉-2,5-二酮开环共聚合反应,分别合成出具有可控组成及结构的共聚物,后经脱保护反应获得具有生物可降解性和生物安全性的聚(DL-乳酸-co-L-丝氨酸)和聚(L-乳酸-co-L-丝氨酸)。
(7)基于相关实验数据对比并讨论了：①3-苄氧羰基亚乙基-6-甲基-吗啉-2,5-二酮(BCEMD)与(3S)-苄氧甲基-(6RS)-甲基-吗啉-2,5-二酮的单体活性[(3S，6RS)-BMMD];②乙醇酸双环胍(TBDG)和乳酸双环胍(TBDL)的催化剂活性；③聚合反应温度的选取问题。
With the development of polymer science and the deepening of research works, copolymers of a-hydroxy acid and a-amino acid (polydepsipeptides) are greatly valued by scientists and researchers in the field of biomedical polymer science. Polydepsipeptides have the advantages of both polyesters and polyamino acids, and simultaneously they also have better hydrophilicity and cell adhesion than polyesters do, have better solubility and processability than polyamino acids do, etc. Polydepsipeptides possess broad application prospects in the biomedical field, such as that they can be used as carriers for controlled release drug delivery systems, cell growth vectors, surgical sutures, medical dressings and so on.
The innovative research works reported in this dissertation are mainly about preparation of copolymers of lactic acid and serine or copolymers of lactic acid and glumatic acid via Ring-Opening Polymerization of morpholine-2,5-diones catalyzed by biomimetic non-toxic metal-free organic guanidium salt catalysts. The specific contents are described as follows:
(1) Copolymers with controllable composition and high isotacticity were synthesized via the living and stereospecific ring-opening copolymerization of L-lactide and (3S)-benzyloxymethyl-(6S)-methyl-morpholine-2,5-dione catalyzed by creatinine acetate, and via deprotection reactions the biodegradable and bio-safe poly(L-lactic acid-co-L-serine)s were obtained then.
(2) Two new type biomimetic non-toxic metal-free organic guanidium salt catalysts bicyclic guanidium glycolate (TBDG) and bicyclic guanidium lactate (TBDL) were synthesized via the reaction of bicyclic guanidine (1,5,7-triaza-bicyclo-[4.4.0]-dec-5-ene, TBD) and glycolic acid or lactic acid respectively.
(3) A new compound3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione (BCEMD) was synthesized from the starting material L-glumatic acid via three-step organic reaction.
(4) Homopolymers PBCEMDs were synthesized via the ring-opening homopolymerization of3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione catalyzed by bicyclic guanidium glycolate, and via deprotection reactions the biodegradable and bio-safe poly(lactic acid-alt-glutamic acid)s were obtained then; It was proved that the polymerization possessed characteristics of living polymerization via kinetic experiments for the polymerization; It was certified that the mechanism of the polymerization should be coordination-insertion mechanism via the experiments of adding terminate agents and the characterization of macromolecular active species.
(5) Copolymers with controllable composition and structure were synthesized via the ring-opening copolymerization of DL-lactide and3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione catalyzed by bicyclic guanidium glycolate, and via deprotection reactions the biodegradable and bio-safe poly(lactic acid-co-glutamic acid)s were obtained then.
(6) Copolymers with controllable composition and structure were synthesized via the ring-opening copolymerization of lactide and3-benzyloxymethyl-6-methyl-morpholine-2,5-dione catalyzed by bicyclic guanidium glycolate or bicyclic guanidium lactate respectively, and via deprotection reactions the biodegradable and bio-safe poly(DL-lactic acid-co-L-serine)s and poly(L-lactic acid-co-L-serine)s were obtained then.
(7) Make some comparisons and discussions based on the related experimental data:①the monomer activities of3-[(benzyloxycarbonyl)-ethylene]-6-methyl-morpholine-2,5-dione (BCEMD) and (3S)-benzyloxymethyl-(6RS)-methyl-morpholine-2,5-dione [(3S,6RS)-BMMD];②the catalyst activities of bicyclic guanidium glycolate (TBDG) and bicyclic guanidium lactate (TBDL);③the problem of selecting the temperature of copolymeriztions.
引文
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