Synthesis of an aspartame precursor by immobilized thermolysin in an organic solvent
Synthesis of an aspartame precursor by immobilized thermolysin in an organic solvent
复制标题
有机溶剂中固定化嗜热菌蛋白酶合成阿斯巴甜前体
DOI：
10.1021/jo00338a045
复制
发表时间：
1981
影响因子：
3.6
通讯作者：
T. Hashimoto
中科院分区：
文献类型：
--
作者：
K. Oyama;S. Nishimura;Y. Nonaka;K. Kihara;T. Hashimoto
合成N-（苄氧基羰基）-L-乙酰基-L-苯丙氨酸甲酯，合成甜味剂甜菊糖的前体，来自IV-通过使用用各种方法固定化的嗜热菌蛋白酶，在有机溶剂的表观单相中进行（苄氧基-羰基）-L-天冬氨酸和L-苯丙氨酸甲酯的合成。蛋白酶催化的肽合成已经引起越来越多的关注，1并且在许多情况下合成是基于产物的沉积，2，导致平衡向不太有利的产品转移。3从实用的观点来看，使用固定化酶是很有价值的，4但在酶促肽合成中，由于固定化酶与沉积产物分离的问题，固定化酶的使用是相当不切实际的。最近，Kuhl等人已经表明，固定化酶可以通过采用两相水-有机体系应用于肽合成。然而，这种方法仍然是不令人满意的，因为我们发现，柱操作，一个大的吸引力与固定化酶系统，是困难的，由于在固定化酶的填充床的两个层的沟道。本文对酶法合成二肽甜味剂苯丙氨酸的研究进行了扩展，报道了在有机溶剂的表观单相中，利用固定化嗜热菌蛋白酶合成甜味剂前体N-（苄氧羰基）-L-乙酰基-L-苯丙氨酸甲酯的新方法。
The synthesis of N-(benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester, the precursor of the synthetic sweetener aspartame, from lV-(benzyloxy-carbonyl)-L-aspartic acid and L-phenylalanine methyl ester was carried out in an apparent single phase of the organic solvent by using thermolysin immobilized with various methods.Sir: Proteinase-catalyzed syntheses of peptides have been drawing increasing attention, 1 and in many cases the synthesis is based on the deposition of a product, 2 which causes the shift of the equilibrium toward a less favorable product. 3 From the practical point of view the use of an immobilized enzyme is of great value, 4 but it is rather impractical in the enzymatic peptide syntheses because of the problem of the separation of an immobilized enzyme from a deposition product. Recently Kuhl et al. have shown that an immobilized enzyme could be applied to the peptide synthesis by employing biphasic water-organic systems. 5 However, this approach is still unsatisfactory, since we found that the column operation, one big at-traction with an immobilized enzyme system, is difficult due to the channeling of the two layers in a packed bed of an immobilized enzyme. We extended our research6 on the enzymatic synthesis of the dipeptide sweetner aspar-tame7 and report the new approach to the synthesis of jV-(benzyloxycarbonyl)-L-aspartyl-L-phenylalanine methyl ester, the precursor of the sweetener, by using immobilized thermolysin in an apparent singlephase of an organic solvent.