A green route for the synthesis of a bitter-taste dipeptide combining biocatalysis, heterogeneous metal catalysis and magnetic nanoparticles

Autor(es)

Ungaro, Vitor A. ^[1] ; Liria, Cleber W. ^[1] ; Romagna, Carolina D. ^[1] ; Costa, Natalia J. S. ^[2] ; Philippot, Karine ^[3] ; Rossi, Liane M. ^[2] ; Teresa Machini, M. ^[1]

Afiliação do(s) autor(es)

^[1] Univ Sao Paulo, Inst Chem, Dept Biochem, BR-05508900 Sao Paulo - Brazil

^[2] Univ Sao Paulo, Inst Chem, Dept Fundamental Chem, BR-05513970 Sao Paulo, SP - Brazil

^[3] Univ Toulouse, UPS, INPT, CNRS, LCC, F-31077 Toulouse 4 - France

• Tipo de documento: Artigo Científico
• Fonte: RSC ADVANCES; v. 5, n. 46, p. 36449-36455, 2015.
• Citações Web of Science: 4

Resumo

There is increasing demand for green technologies to produce high-solubility and low-toxicity compounds with potential application in the food industry. This study aimed to establish a clean, synthetic route for preparing the bitter-taste dipeptide Ala-Phe, a potential substitute for caffeine as a food additive. Synthesis of Z-Ala-Phe-OMe starting from Z-Ala-OH and HCl center dot Phe-OMe was catalysed by thermolysin at 50 degrees C in buffer (step 1). Z-Ala-Phe-OMe ester hydrolysis to give Z-Ala-Phe-OH at 37 degrees C in 30% acetonitrile/buffer was catalysed by alpha-bovine chymotrypsin (alpha CT), protease with esterase activity (step 2). Hydrogenation of Z-Ala-Phe to give the desired Ala-Phe was catalysed by C/Pd in methanol (step 3). Steps 2 and 3 were optimized by using the magnetically recoverable recycling enzyme Fe3O4@silica-alpha CT and the magnetically recoverable metal nanocatalyst Fe3O4@silica-Pd, respectively. This inspiring combination of technologies and the original results demonstrate the suitability of using enzymes, metal catalyst and magnetic nanoparticles for easy, economical, stereoselective, clean production of an important target compound. Besides, they add to the development of peptide chemistry and catalysis. (AU)

• Processo FAPESP: 08/11695-1 - Tecnologias alternativas na química de peptídeos: solvólise mediada por íons metálicos, biocatálise, aquecimento convencional e microondas
• Beneficiário: Maria Teresa Machini
• Modalidade de apoio: Auxílio à Pesquisa - Regular
• Processo FAPESP: 12/09068-4 - Microondas, biocatálise, íons metálicos divalentes e nanotecnologia na síntese de peptídeos
• Beneficiário: Maria Teresa Machini
• Modalidade de apoio: Auxílio à Pesquisa - Regular