由井冈霉素、阿卡波糖及其衍生物制备维列胺的研究
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摘要
维列胺是一个不饱和C7N氨基环醇,其结构类似α-D-葡萄糖,是各种α-糖苷酶抑制剂的核心结构,利用其N-取代物可合成其它活性更强的糖苷酶抑制剂。阿卡波糖和伏格列波糖可以竞争性抑制α-葡萄糖苷酶,减缓糖类的吸收,是临床上广泛使用的治疗II型糖尿病的降糖药物。
维列胺除化学合成外,主要由含维列胺结构的化合物来制备。井冈霉素和阿卡波糖结构中都含有维列胺,可经生物转化或化学裂解产生维列胺。阿卡波糖化学裂解法迅速高效,不产生副产物井冈霉胺,但原料成本较高。井冈霉素生物转化产率低、周期长,会产生井冈霉胺。本文进行了由阿卡波糖和井冈霉素制备维列胺的研究。
本文首先研究了维列胺、阿卡波糖和井冈霉素的检测方法,建立了毛细管区带电泳的分析方法,可同时对维列胺制备过程的底物和产物进行检测,极大提高了检测效率。
本文通过酸、碱和离子交换树脂与阿卡波糖或井冈霉素反应,发现井冈霉素经酸、碱、离子交换树脂法都不能产生维列胺。三氟乙酸及离子交换树脂水解阿卡波糖能产生维列胺,但维列胺的产率较低。碱裂解阿卡波糖产生维列胺产率最高,阿卡波糖与NaOH质量比1∶4时,121℃裂解30min,维列胺产率最高可达84.2%。阿卡波糖发酵的衍生物杂质C,经NaOH裂解也得到了维列胺,转化率与阿卡波糖相同。
从实验室菌种库中筛选了4株井冈霉素转化菌,其中SIPI-V08转化效果最好,SIPI-V01和SIPI-V29稍弱,SIPI-V23转化率最低。对它们进行了维列胺的生物转化研究,优化了转化液和转化条件。采用4株转化菌的静息细胞进行转化,维列胺的转化率没有显著提高。
井冈霉素降解为维列胺是多步酶反应的过程,每步反应的酶活力都不相同,可能有一种酶成为限速酶。即使是催化同一步反应的酶,不同菌种的酶活力也有很大差异,当不同来源的菌种混合进行转化时,可能形成互补,提高总转化率。采用4株转化菌进行混合转化,结果发现部分组合的混合转化能显著提高转化率,高于各自单独转化的最高值。SIPI-V08-V23、SIPI-V01-V08、SIPI-V01-V08-V23的混合时转化效果最好。混合转化也能降低高浓度底物对菌种的抑制,在10%的底物浓度下也能迅速转化。10%底物浓度下静息细胞混合转化总转化率显著提高,转化周期比单独转化缩短一半,SIPI-V08-V23、SIPI-V01-V08-V23、SIPI-V01-V08组合3种组合的混合转化产生的维列胺在第3d就超过了SIPI-V08单独转化6d的5.0mg/ml。SIPI-V08-V23混合在第7d达10.4mg/ml,提高了近一倍。SIPI-V01-V08在第5d维列胺最高为9.2mg/ml。
Valienamine is an unsaturated aminocyclitol compound. The absolute configuration of valienamine is similar to that of a-D-glucose, and it demonstrates strong inhibitory activity against glucosidase. As the key moiety of variousα-glucosidase inhibitors, valienamine can be used as a chemical intermediate in the synthesis of other strong aglycoside inhibitors, such as acarbose and voglibose, which are most widely used drugs for type II diabetes mellitus at present due to their strong ability to delay the absorption of carbohydrates by competitive inhibition of intestinalα-glucosidases.
Both of Acarbose and validamycin A have a valienamine moiety in their structure s. Besides chemical synthesis, valienamine is mainly produced by cleavage of Acarbose, which is effective but costly, or by degradation of validamycin A, which has a low efficiency and produces impurities. In this paper, the methods for preparation of valienamine by acarbose and validamycin A are completely discussed in details. A new method——capillary electrophoresis is also established for the analysis of valienamine, acarbose and validamycins, which makes a great progress in analysis efficiency.
It was found in this research that no valienamine was produced after reaction of validamycin A with acid, base or ion exchange resin. Although acarbose could react with trifluoroacetic acid or ion exchange resin to produce valienamine, the yield is very low.
However, the highest yield of valienamine was finally obtained through the reaction of acarbose with sodium hydroxide for about 30min at 121℃. The most desirable ratio between acarbose and sodium hydroxide is 1 to 4, and the highest valienamine yield could reach 84.2%. Valienamine could also be obtained with the same efficiency of transformation as acarbose when an acarbose derivative, component C in the fermentation broth, was reacted with sodium hydroxide.
Four strains with the ability to convert validamycins to valienamine were isolated from the laboratory collection of strains, in which strain SIPI-V08 has the highest efficiency of transformation. The transformation efficiency of strain SIPI-V01 and SIPI-V29 are lower, and strain SIPI-V23 the lowest. The yiled of valienamine was obviously improved through optimization of fermentation medium and condition. The relationship between resting cells cultivation and transformation efficiency was also studied, but the result did not turn out to be satisfactory.
The conversion of validamycin A to valienamine was completed via three steps of enzymatic catalytic reactions involved in several different enzymes. When different strains were co-incubated, the total yield of valienamine could be greatly improved by complementary effect resulting from the interaction of various enzymes in them. Thus, mixed transformations of four strains were studied, and some combinations of the strains resulted in great increase in total yield. The best result comes from the mixed transformation of strain SIPI-V08-V23、SIPI-V01-V08、SIPI-V01-V08-V23. On the other hand, the inhibition of transformation by high concentration of substrate could be strongly attenuated with mixed transformation. Even if the substrate concentration is up to 10%, the transformation could be efficiently performed. The mixed transformation at 10% substrate concentration by resting cells cultivation was also studied and the yield was significantly improved. Meanwhile the total cultivation time was half-shortened as well. The valienamine yield by mixed transformation of strain SIPI-V08-V23、SIPI-V01-V08 or SIPI-V01-V08-V23 exceeded 5.0mg/ml on the 3rd day, however, it required 6 days for strain SIPI-V08 alone to reach the same yield. Valienamine yield by strain SIPI-V08-V23 could reach the maximum 10.4mg/ml on the 7th day and the yield by strain SIPI-V01-V08 could reach the maximum 9.2mg/ml on the 5th day.
维列胺除化学合成外,主要由含维列胺结构的化合物来制备。井冈霉素和阿卡波糖结构中都含有维列胺,可经生物转化或化学裂解产生维列胺。阿卡波糖化学裂解法迅速高效,不产生副产物井冈霉胺,但原料成本较高。井冈霉素生物转化产率低、周期长,会产生井冈霉胺。本文进行了由阿卡波糖和井冈霉素制备维列胺的研究。
本文首先研究了维列胺、阿卡波糖和井冈霉素的检测方法,建立了毛细管区带电泳的分析方法,可同时对维列胺制备过程的底物和产物进行检测,极大提高了检测效率。
本文通过酸、碱和离子交换树脂与阿卡波糖或井冈霉素反应,发现井冈霉素经酸、碱、离子交换树脂法都不能产生维列胺。三氟乙酸及离子交换树脂水解阿卡波糖能产生维列胺,但维列胺的产率较低。碱裂解阿卡波糖产生维列胺产率最高,阿卡波糖与NaOH质量比1∶4时,121℃裂解30min,维列胺产率最高可达84.2%。阿卡波糖发酵的衍生物杂质C,经NaOH裂解也得到了维列胺,转化率与阿卡波糖相同。
从实验室菌种库中筛选了4株井冈霉素转化菌,其中SIPI-V08转化效果最好,SIPI-V01和SIPI-V29稍弱,SIPI-V23转化率最低。对它们进行了维列胺的生物转化研究,优化了转化液和转化条件。采用4株转化菌的静息细胞进行转化,维列胺的转化率没有显著提高。
井冈霉素降解为维列胺是多步酶反应的过程,每步反应的酶活力都不相同,可能有一种酶成为限速酶。即使是催化同一步反应的酶,不同菌种的酶活力也有很大差异,当不同来源的菌种混合进行转化时,可能形成互补,提高总转化率。采用4株转化菌进行混合转化,结果发现部分组合的混合转化能显著提高转化率,高于各自单独转化的最高值。SIPI-V08-V23、SIPI-V01-V08、SIPI-V01-V08-V23的混合时转化效果最好。混合转化也能降低高浓度底物对菌种的抑制,在10%的底物浓度下也能迅速转化。10%底物浓度下静息细胞混合转化总转化率显著提高,转化周期比单独转化缩短一半,SIPI-V08-V23、SIPI-V01-V08-V23、SIPI-V01-V08组合3种组合的混合转化产生的维列胺在第3d就超过了SIPI-V08单独转化6d的5.0mg/ml。SIPI-V08-V23混合在第7d达10.4mg/ml,提高了近一倍。SIPI-V01-V08在第5d维列胺最高为9.2mg/ml。
Valienamine is an unsaturated aminocyclitol compound. The absolute configuration of valienamine is similar to that of a-D-glucose, and it demonstrates strong inhibitory activity against glucosidase. As the key moiety of variousα-glucosidase inhibitors, valienamine can be used as a chemical intermediate in the synthesis of other strong aglycoside inhibitors, such as acarbose and voglibose, which are most widely used drugs for type II diabetes mellitus at present due to their strong ability to delay the absorption of carbohydrates by competitive inhibition of intestinalα-glucosidases.
Both of Acarbose and validamycin A have a valienamine moiety in their structure s. Besides chemical synthesis, valienamine is mainly produced by cleavage of Acarbose, which is effective but costly, or by degradation of validamycin A, which has a low efficiency and produces impurities. In this paper, the methods for preparation of valienamine by acarbose and validamycin A are completely discussed in details. A new method——capillary electrophoresis is also established for the analysis of valienamine, acarbose and validamycins, which makes a great progress in analysis efficiency.
It was found in this research that no valienamine was produced after reaction of validamycin A with acid, base or ion exchange resin. Although acarbose could react with trifluoroacetic acid or ion exchange resin to produce valienamine, the yield is very low.
However, the highest yield of valienamine was finally obtained through the reaction of acarbose with sodium hydroxide for about 30min at 121℃. The most desirable ratio between acarbose and sodium hydroxide is 1 to 4, and the highest valienamine yield could reach 84.2%. Valienamine could also be obtained with the same efficiency of transformation as acarbose when an acarbose derivative, component C in the fermentation broth, was reacted with sodium hydroxide.
Four strains with the ability to convert validamycins to valienamine were isolated from the laboratory collection of strains, in which strain SIPI-V08 has the highest efficiency of transformation. The transformation efficiency of strain SIPI-V01 and SIPI-V29 are lower, and strain SIPI-V23 the lowest. The yiled of valienamine was obviously improved through optimization of fermentation medium and condition. The relationship between resting cells cultivation and transformation efficiency was also studied, but the result did not turn out to be satisfactory.
The conversion of validamycin A to valienamine was completed via three steps of enzymatic catalytic reactions involved in several different enzymes. When different strains were co-incubated, the total yield of valienamine could be greatly improved by complementary effect resulting from the interaction of various enzymes in them. Thus, mixed transformations of four strains were studied, and some combinations of the strains resulted in great increase in total yield. The best result comes from the mixed transformation of strain SIPI-V08-V23、SIPI-V01-V08、SIPI-V01-V08-V23. On the other hand, the inhibition of transformation by high concentration of substrate could be strongly attenuated with mixed transformation. Even if the substrate concentration is up to 10%, the transformation could be efficiently performed. The mixed transformation at 10% substrate concentration by resting cells cultivation was also studied and the yield was significantly improved. Meanwhile the total cultivation time was half-shortened as well. The valienamine yield by mixed transformation of strain SIPI-V08-V23、SIPI-V01-V08 or SIPI-V01-V08-V23 exceeded 5.0mg/ml on the 3rd day, however, it required 6 days for strain SIPI-V08 alone to reach the same yield. Valienamine yield by strain SIPI-V08-V23 could reach the maximum 10.4mg/ml on the 7th day and the yield by strain SIPI-V01-V08 could reach the maximum 9.2mg/ml on the 5th day.
引文
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