Process for the enzymatic synthesis of alkyl esters of peptides

Details Process for the enzymatic synthesis of alkyl esters of peptides Process for the enzymatic synthesis of alkyl esters of peptides

1994-10-31

1996-09-10

Naff, David M.

Chemistry: molecular biology and microbiology

Micro-organism, tissue cell culture or enzyme using process...

Enzymatic production of a protein or polypeptide

435135, 424491, 514 2, 514937, C12P 2106, C12P 762, A61K 916, A61K 3801

Patent

active

055545084

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to a process for the enzymatic synthesis, called process for the enzymatic alcoholysis of proteins, which makes it possible to obtain peptide esters. The invention also relates to the products obtained by the process, as well as the use of these products as additives and ingredients in food, cosmetic and pharmaceutical and chemical products.
Because of their large quantity and their advantageous properties, proteins of animal origin (collagen, casein, gelatin and the like) and plant origin and their peptide derivatives constitute excellent raw materials for the chemical, food, pharmaceutical and cosmetic industries.
For example, International Patent Application WO-A-90/03123 describes the manufacture of microparticles of proteins intended to be used as fat substitutes in food products. Microparticles are manufactured by adding a solution of hydrophobic proteins, for example a prolamine, in alcoholic medium, to an aqueous medium. The protein is precipitated in the form of microparticles. Before being brought into contact with the aqueous medium, the protein may be subjected to an enzymatic hydrolysis. In this case, the microparticles consist of polypeptides having a molar mass of about 1000 daltons.
In the cosmetic field, peptide preparations are desired for their emulsifying power, their water-retaining power, their conditioning effect for shampoos and their emollient power. The peptides used have a molar mass which is most often less than 10,000 and rather less than 5000. They are generally obtained by the enzymatic route.
The use of proteins of plant origin in the cosmetic field is particularly desired.
For example, the use of peptides of gluten with a molar mass of less than 10,000, preferably of between 3000 and 5000, has been proposed because of their water-retaining power and their conditioning effect (JP-63253012). Such peptides are obtained by enzymatic hydrolysis with the aid of Alcalase, pepsin or acid protease from Aspergillus niger.
Peptide esters have also been proposed for cosmetic applications (JP-60097043, JP-60097042, JP-60084209). These peptide esters are obtained by condensing a peptide with a fatty or polyhydroxylated ester of an amino acid, catalyzed by a cysteine protease (EC 3.4.22).
Although the processes described up until now for the manufacture of protein derivatives are relatively efficient, they have nevertheless certain disadvantages. For example, microbial contamination of the reaction medium often poses a problem, the operating conditions favoring the growth of microorganisms. In addition, during a hydrolysis in aqueous medium, the molar mass of the product is difficult to control and the reaction often results in products with a molar mass less than that desired.
The process of the invention was therefore designed with the aim of developing an economical process which makes it possible to upgrade proteins of plant and animal origin, even in a crude state, for the manufacture of peptides and peptide esters, while minimizing the risk of microbial contamination of the medium.
The inventors have developed a process for the treatment of protein substrates which occurs in an alcoholic medium and which is catalyzed by an enzyme which is both proteolytic and esterolytic.
The esterase activity of certain enzymes known for their capacity to hydrolyze peptide bonds (peptide hydrolysates, EC 3.4.) is characterized by the possibility of catalyzing the hydrolysis of alkyl ester bonds of amino acids or of synthetic peptides present at low concentration in a buffered aqueous solution.
The inventors have observed that certain enzymes which possess both a protease and esterase activity lead to the synthesis of peptide esters when the substrate is a mixture of proteins or peptides present in an alcoholic medium and under certain conditions of pH. The enzyme uses alcohol in the place of water to cut the peptide bond between 2 amino acids of a protein or a peptide, or is capable of catalyzing the condensation of a peptide via its terminal carboxyl group with the al

REFERENCES:
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patent: 5021248 (1991-06-01), Stark et al.
patent: 5145702 (1992-09-01), Stark et al.
Vidulac et al. (1983) Tetrahedron, 39(2), 269-274.
Morihara et al. (1987) Trends in Biotechnol, 5, 164-170.
Agricultural And Biological Chemistry, vol. 52, No. 3, 1988, pp. 855-856, H. Saito et al, "Papain-catalyzed Hydrolysis in an Aqueous Organic System" .

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