RESUMEN
Unprotected L-phenylalanine was derivatized by an innovative enzymatic method by means of laccases from Pycnoporus cinnabarinus and Myceliophthora thermophila. During the incubation of L-phenylalanine with para-hydroquinones using laccase as biocatalyst, one or two main products were formed. Dependent on the substitution grade of the hydroquinones mono- and diaminated products were detected. Differences of the used laccases are discussed. The described reactions are of interest for the derivatization of amino acids and a synthesis of pharmacological-active amino acid structures in the field of white biotechnology.
Asunto(s)
Carbono/metabolismo , Proteínas Fúngicas/metabolismo , Hidroquinonas , Lacasa/metabolismo , Nitrógeno/química , Fenilalanina , Carbono/química , Hidroquinonas/química , Hidroquinonas/metabolismo , Estructura Molecular , Fenilalanina/química , Fenilalanina/metabolismo , Pycnoporus/enzimologíaRESUMEN
We have studied the enzymatic derivatization of amino acids by use of the polyphenol oxidase laccase. Derivatization of L-tryptophan was achieved by enzymatic crosslinking with the laccase substrate 2,5-dihydroxy-N-(2-hydroxyethyl)-benzamide. The main product (yield up to 70%) was identified as the quinoid compound 2-[2-(2-hydroxy-ethylcarbamoyl)-3,6-dioxo-cyclohexa-1,4-dienylamino]-3-(1H-indol-3-yl)- propionic acid and demonstrates that laccase-catalyzed C-N-coupling occurred on the amino group of the aliphatic side chain. These enzyme based reactions provide a simple and fast method for the derivatization of unprotected amino acids.
Asunto(s)
Benzamidas/química , Hidroquinonas/química , Lacasa/metabolismo , Triptófano/análogos & derivados , Hidroquinonas/metabolismo , Lacasa/aislamiento & purificación , Triptófano/química , Triptófano/metabolismoRESUMEN
[reaction: see text]. A new one-pot procedure for the efficient synthesis of a small library of amino-functionalized tetrahydroisoindole-1,3-dione derivatives was developed. This three-component coupling reaction comprises subsequent condensation and Diels-Alder reactions of ubiquitous available starting materials (alpha,beta-unsaturated aldehydes, amide, and maleimide). The synthesized compounds share a substituted tetrahydroisoindole motif in an endo fashion.
