| Full text | |
| Author(s): |
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]
Total Authors: 7
|
| Affiliation: | [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
Total Affiliations: 3
|
| Document type: | Journal article |
| Source: | RSC ADVANCES; v. 5, n. 46, p. 36449-36455, 2015. |
| Web of Science Citations: | 4 |
| Abstract | |
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) | |
| FAPESP's process: | 08/11695-1 - Alternative technologies in peptide chemistry: metal ion-promoted solvolysis, biocatalysis, conventional heating and microwave heating |
| Grantee: | Maria Teresa Machini |
| Support Opportunities: | Regular Research Grants |
| FAPESP's process: | 12/09068-4 - Microwaves, biocatalysis, divalent metal ions and nanotechnology in peptide synthesis |
| Grantee: | Maria Teresa Machini |
| Support Opportunities: | Regular Research Grants |