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One-Pot Synthesis of Diverse dl-Configuration Dipeptides by a Streptomyces d-Stereospecific Amidohydrolase ▿ †

机译:链霉菌d-立体特异性酰胺水解酶一锅法合成不同的dl-构型二肽

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摘要

The synthesis of diverse dl-configuration dipeptides in a one-pot reaction was demonstrated by using a function of the aminolysis reaction of a d-stereospecific amidohydrolase from Streptomyces sp., a clan SE, S12 family peptidase categorized as a peptidase with d-stereospecificity. The enzyme was able to use various aminoacyl derivatives, including l-aminoacyl derivatives, as acyl donors and acceptors. Investigations of the specificity of the peptide synthetic activity revealed that the enzyme preferentially used d-aminoacyl derivatives as acyl donors. In contrast, l-amino acids and their derivatives were preferentially used as acyl acceptors. Consequently, the synthesized dipeptides had a dl-configuration when d- and l-aminoacyl derivatives were mixed in a one-pot reaction. This report also describes that the enzyme produced cyclo(d–Pro-l-Arg), a specific inhibitor of family 18 chitinase, with a conversion rate for d-Pro benzyl ester and l-Arg methyl ester to cyclo(d-Pro–l-Arg) of greater than 65%. Furthermore, based on results of cyclo(d-Pro–l-Arg) synthesis, we propose a reaction mechanism for cyclo(d-Pro–l-Arg) production.
机译:一锅反应中多种dl构型二肽的合成通过使用链霉菌属(Streptomyces sp。)的d-立体特异性酰胺水解酶的家族分解功能来证明,该家族SE,S12家族肽酶归类为具有d-立体特异性的肽酶。该酶能够使用各种氨基酰基衍生物,包括1-氨基酰基衍生物,作为酰基供体和受体。对肽合成活性特异性的研究表明,该酶优先使用d-氨基酰基衍生物作为酰基供体。相反,优先将1-氨基酸及其衍生物用作酰基受体。因此,当将d-和1-氨基酰基衍生物在一锅反应中混合时,合成的二肽具有dl-构型。该报告还描述了该酶产生的环(d-Pro-l-Arg)是18几丁质酶的特异性抑制剂,d-Pro苄基酯和l-Arg甲基酯向环(d-Pro- 1-Arg)大于65%。此外,基于环(d-Pro-1-Arg)合成的结果,我们提出了环(d-Pro-1-Arg)生产的反应机理。

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