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WO1986003944A1 - Succedane du sel de table comprenant un peptide thermostabilise - Google Patents

Succedane du sel de table comprenant un peptide thermostabilise Download PDF

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Publication number
WO1986003944A1
WO1986003944A1 PCT/US1986/000004 US8600004W WO8603944A1 WO 1986003944 A1 WO1986003944 A1 WO 1986003944A1 US 8600004 W US8600004 W US 8600004W WO 8603944 A1 WO8603944 A1 WO 8603944A1
Authority
WO
WIPO (PCT)
Prior art keywords
gum
cycloalkyl
peptide
dipeptide
ornithine
Prior art date
Application number
PCT/US1986/000004
Other languages
English (en)
Inventor
Patrick J. Joyce
Original Assignee
Joyce Patrick J
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Joyce Patrick J filed Critical Joyce Patrick J
Publication of WO1986003944A1 publication Critical patent/WO1986003944A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/20—Synthetic spices, flavouring agents or condiments
    • A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
    • A—HUMAN NECESSITIES
    • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
    • A23L—FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES, NOT OTHERWISE PROVIDED FOR; PREPARATION OR TREATMENT THEREOF
    • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
    • A23L27/40—Table salts; Dietetic salt substitutes
    • A23L27/45—Salt substitutes completely devoid of sodium chloride

Definitions

  • the general field of the present invention is new heat stable dipeptide salty tasting compounds which are capable of being substituted for sodium and potassium chloride seasoning agents in baking and cooking.
  • a process for salting, i.e., seasoning, comestibles with these new peptide salt substitutes is also described, as well as a novel food composition for making such process operable.
  • the particular new salty peptides are uniquely characterized in that they are heat stable and do not decompose when added to edible food compositions which are to be baked or cooked at or above or about 360°F before consumption.
  • DKP which is readily formed in all normally structured dipeptides formed by the union of two normally structured amino acids.
  • the object of the present invention is to describe and claim such a prouct and to illustrate to those skilled in the art of food chemistry how to employ such a new and unique composition of matter.
  • the present invention comprises a heat stable peptide salt composition which includes a peptide component composed of a plurality of amino acid residue components, at least one of which has been modified to include a cycloalkyl bridge in the structure and, in some cases, an edible hydrocolloidal gum.
  • the composition in its preferred product form comprises a soluble powder which is readily miscible with other food additives and food formulas.
  • cycloalkyl as employed in this specifica ⁇ tion is intended to refer to such cyclic functions as cyclo- propyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like which are by means of their manner of preparation built into the particular amino acid concerned.
  • modified amino acids When these modified amino acids are noted herein, they will be distinguished in some cases by the symbol " ⁇ « prefixed to the name or abbreviation of the amino acid.
  • This added alkyl function has been found to act as a stabilizer of the peptide link between amino acids, at least one of which must exhibit the unique configuration.
  • the preferred peptide components are dipeptides of the normal or cycloalkyl substituted amino acids taurine .or ornithine coupled with such amino acids as cycloalkyl sub ⁇ stituted ornithine cycloalkyl substituted lysine or cycloalkyl substituted alanine.
  • These compounds and their mineral acid salts and lower alkyl esters exhibit unusual thermal stability, especially when complexed with a quantity of an edible hydro- colloidal gum such as gum acacia or gum tragacanth.
  • the hydrocolloidal gum is preferably a polysaccharide type hydrocolloidal gum, such as gum acacia, gum tragacanth, pectin gum, gum karaya, guar gum, larch gum, psyllium seed gum, or locust bean gum, for instance.
  • a polysaccharide type hydrocolloidal gum such as gum acacia, gum tragacanth, pectin gum, gum karaya, guar gum, larch gum, psyllium seed gum, or locust bean gum, for instance.
  • a major amount of the hydrocolloidal gum is complexed with a minor amount of the peptide after moistening the dry mix with a water to form a paste. If it is desired, one may dry by known means such as spray drying, drum drying, etc. the complex to form a powder for use in baking or cooking of foods in place of ordinary table salt, i.e., sodium chloride.
  • the new peptide containing table salt substitute comprises a soluble complex of:
  • R represents either hydrogen or a lower alkyl group of C-
  • n is a positive integer from 1 to 4, but preferably 1, and x can be either 1 or 2, depending on whether the cycloalkyl amino acid coupled to taurine is a cycloalkyl ornithine or a cycloalkyl lysine.
  • a thermally stabilizing amount of a hydrocol ⁇ loidal gum such as gum acacia or gum tragacanth.
  • the ratio of the amounts of the peptide and gum components in the complex will vary depending on the end use and the food composition being sweetened and the textural requirements of the end product. Generally, 5 to 10 parts of gum are used for each part by weight of peptide, but as much as 100 parts of the former to 1 part of the latter might be useful in some food applications. In still other uses, a minor amount of gum to the peptide could be considered. In the most preferred applications, a major amount of gum to a minor amount of peptide is needed to promote heat stability.
  • a second preferred product aspect of this invention is the peptide ingredients themselves such as the compounds of (1A), (2A), and (3A) hereinabove.
  • the R represents either hydrogen or a lower alkyl function' such as methyl, ethyl, propyl, or butyl, for instance, either normal or isomeric in configuration or benzyl
  • x is either 1 or 2
  • n is a positive integer from 1 to 4, and hence represents either cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl functions.
  • a third preferred product aspect of the invention is a food composition which requires a salty material as one of its essential ingredients.
  • a cake mix formula for instance, where the peptide to gum ratio is critical to gain heat stabil ⁇ ity and concurrent satisfactory texture and other ingredient compatibility.
  • a new peanut butter formula or a pretzel or potato chip dough or pasta dough which can taste like sodium chloride laden dough but actually be salt free is contemplated.
  • One preferred process aspect of the present invention is the synthesis of a new salty tasting peptide by means of the following reaction: ornithine amino acid + cyclopropyl alanine > salty peptide
  • the known a in ⁇ acid ornithine is reacted under well known condensation conditions to form the unique peptide (3A). This is the first time this reaction will have been performed, and-the product obtained will be different than other dipeptides. It will be heat resistant and capable of being complexed with a gum to be heat stable, if desired.
  • a second preferred process aspect of the invention is the formulation of a new and unique cake mix which now becomes feasible for baking in the home.
  • sodium chloride is replaced with the new peptide III or (1A), (2A), or (3A) to obtain when baked a new cake which tastes like known cakes but varies in one material respect. It contains no sodium.
  • a final process aspect of the invention is the pre ⁇ paration of cooked meals and baked foods in the home without the use of sodium or potassium chloride table salts. In a similar manner, this process aspect applies to commercial preparation of prepared food products such as pastas, baked pies, cookies, pretzels, potato chips and corn chips, etc., of many different shapes and formulas.
  • hydrocolloidal poly.saccharide gums are known commercially available materials, the details of which are available in the Encyclopedia of Chemical Technology (3rd. Edition 1983) by Kirk-Othmer, Vol. 12, pages 57-67, published by John Wiley and Sons, New York, NY.
  • gum tragacanth is known to be a mixture of acidic polysac- charides containing galacturonic acid, galactose, fucose,' and xylose and arabinose. It is an exudate from the Astralagus tree found in Iran, Iran, and Turkey. Solutions are weakly acidic with a pH of 5.0 to 6.0, and a molecular weight range of 10,000 to about 250,000. Gum acacia, on the other hand, is a dried exudate obtained from the Acacia tree found chiefly in the African Sudan. It has a large molecular weight of a range of 200,000 to about 1,160,000, and is stable at a slightly acid to neutral range.
  • the alkaline hydrolysis of the hydantoin intermediate 3_ to the cyclopropylornithine amino acid reactant is achieved by suspending 6 grams of the hydantoin _3 from above in 100 mis. of 3 N sodium hydroxide and heating to reflux conditions and maintaining this reflux for 21 hours. At the end of this period, cool the reaction mixture and acidify to pH 6.0 with concentrated hydrochloric acid.
  • the cyclopropyl ornithine amino acid 4_ will precipitate from the solution in good yield. Filter the precipitate out and wash with cold water twice, then with acetone, and dry under high vacuo. Wash three more times with warm anhydrous ethanol to further purify. This product can then be recrystallized from a water/acetone mixture to obtain the cycloalkylamino ornithine amino acid _4 in high yield and excellent purity.
  • Step B Preparation of the Dipeptide of Cyclopropyl ⁇ ornithme and L-Taurine to Obtain a Salty Tasting Peptide 5
  • This peptide is synthesized by known and conventional methods using, however, a new and unique combination of reactive amino acids to yield a heretofore unknown peptide.
  • dibenzyloxycarbonyl ornithine and cyclopropyl alanine benzyl ester are condensed to yield a new corresponding dibenzyloxycarbonyl dipeptide benzyl ester by the mixed anhydride method.
  • This compound when deblocked, is a new peptide.
  • the protecting groups of the dipeptide derivatives are removed by catalytic hydrogenation in acetic acid solution.
  • the product is then treated HC1 -dioxane and obtained as .a hydrochloride salt.
  • the purity of the peptide can be confirmed by melting point, elemental analysis, optical rotation, and thin layer chromatography and NMR and HPLC.
  • Step 1 Preparation of Blocked Peptide as its Benzyl Ester Dissolve the dicyclohexylamine salt of L-ornithine (2.77 grams, 5 mmol) in 30 ml of ethyl acetate. Add 10 is. of 1 molar sulfuric acid to the mixture with constant stirring. Wash the organic layer with distilled water and dry over anhydrous sodium sulfate. Concentrate the solution to dryness in vacuo and dissolve the oily residue in 10 mis of tetra- hydrofuran and 0.55 mis of 5 mmol of N-methylmorpholine. Add 0.5 ml (5 mmol) of ethylchloroformate to this mixture at -5 ⁇ C and hold in this condition for 15 minutes.
  • Step 2 Hydrogenation to Deblock Ester
  • the blocked peptide from step 1 above (0.62 grams or 1.2 mmol) is dissolved in 5 is of acetic acid and hydrogenated in the presence of palladium black at room temperature for 3 hours. Remove the catalyst by filtration and evaporate the filtrate to dryness in vacuo.
  • This complex is the salty flavor ingredient employed as a replacement for sodium chloride in the following Example, which involves the preparation of a new baking formulation useful for baking of naturally tasting yellow cakes, for example, or other baked products. These food products will contain no sodium, yet will have all the attributes of food products prepared and baked using a formula which contains sodium chloride.
  • the sugar ingredient is replaced by the sweetener complex of Example II of the cited copending patent application.
  • the new improved cake formula hence is as follows:
  • Sweetener 208S (from U.S.S.N 680, ,345) 340.5
  • the above margarine is creamed, and the synthetic sweetener as a wet paste is added slowly over 10 minutes with constant stirring till light. The two eggs are then added. along with the vanilla flavor ingredient.. The mixture is then beaten at a moderate speed after each addition.
  • Example IV Repeat the procedure of Example IV, except to substitute 90 parts by weight of gum tragacanth (a water soluble hydrocolloidal polysaccharide gum) for the gum acacia employed in that example.
  • the complex will retain both its sweet and salty flavor during the bake cycle, and the cake obtained will be quite tasty and not able to be distinguished from cakes baked with addition of both sugar and sodium chloride.
  • the edible heat stable dipeptides of the present invention are particularly useful as salting and sweetening agents for baking pies and cakes, breads and other cooked or baked goods which must be heated to temperatures of the order of 350°F in the course of their preparation.

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  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Nutrition Science (AREA)
  • Engineering & Computer Science (AREA)
  • Food Science & Technology (AREA)
  • Polymers & Plastics (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biophysics (AREA)
  • Seasonings (AREA)
  • Peptides Or Proteins (AREA)

Abstract

Un succédané du sel de table thermiquement stable comprend un complexe d'un dipeptide thermostable contenant au moins un reste d'acide aminé de cycloalkyle dans la molécule de peptide et un stabilisateur de gomme de polysaccharide. Des dipeptides préférés sont ceux formés du couplage de taurine avec l'ornithine de cycloalkyle ou la lysine de cycloalkyle, ou bien l'ornithine couplée avec l'alanine de cycloalkyle. Des gommes préférées sont la gomme adragante ou la gomme arabique qui sont complexées avec des peptides. Le rapport entre le peptide et la gomme peut varier considérablement en fonction de l'utilisation finale de la composition d'assaisonnement et de la texture que l'on désire donner au produit.
PCT/US1986/000004 1985-01-03 1986-01-02 Succedane du sel de table comprenant un peptide thermostabilise WO1986003944A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US68850785A 1985-01-03 1985-01-03
US688,507 1985-01-03
US71666885A 1985-03-27 1985-03-27
US716,668 1985-03-27

Publications (1)

Publication Number Publication Date
WO1986003944A1 true WO1986003944A1 (fr) 1986-07-17

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EP (1) EP0205610A4 (fr)
WO (1) WO1986003944A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0950663A4 (fr) * 1997-08-01 2003-03-19 Toray Industries Stabilisation de proteines utiles et compositions a base de proteines utiles
US10201175B2 (en) 2012-03-30 2019-02-12 Givaudan Sa N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds
US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds
US10582715B2 (en) 2012-03-30 2020-03-10 Givaudan Sa Powder flavour composition
US10645955B2 (en) 2012-03-30 2020-05-12 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
US10711230B2 (en) 2012-03-30 2020-07-14 Givaudan Sa N-acyl proline derivatives as food flavoring compounds
US10834950B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10836712B2 (en) 2012-03-30 2020-11-17 Givaudan S.A. Organic compounds
US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10834943B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds having taste-modifying properties
US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10913922B2 (en) 2012-03-30 2021-02-09 Givaudan S.A. N-acylated methionine derivatives as food flavoring compounds
US10975018B2 (en) 2013-10-02 2021-04-13 Givaudan Sa Organic compounds
US11122826B2 (en) 2013-10-02 2021-09-21 Givaudan Sa Organic compounds
CN115160192A (zh) * 2022-08-02 2022-10-11 南通大学 一种2-胍基乙烷-1-磺酸二十八烷基酯、其制备方法及其用途
US11834393B2 (en) 2013-10-02 2023-12-05 Givaudan Sa Organic compounds having taste-modifying properties

Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3928633A (en) * 1973-12-03 1975-12-23 Gen Foods Corp Sweetening composition and process therefor
US4122195A (en) * 1977-01-24 1978-10-24 General Foods Corporation Fixation of APM in chewing gum
US4384004A (en) * 1981-06-02 1983-05-17 Warner-Lambert Company Encapsulated APM and method of preparation
US4448716A (en) * 1982-03-04 1984-05-15 G. D. Searle & Co. Dipeptide sweetener-metal complexes
WO1985000809A1 (fr) * 1983-08-16 1985-02-28 University Of Georgia Research Foundation, Inc. Synthese de peptides et d'acides amines de cyclopropane

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0204826A4 (fr) * 1984-12-11 1989-02-09 Patrick Joseph Joyce Edulcorants peptidiques thermostables.

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3928633A (en) * 1973-12-03 1975-12-23 Gen Foods Corp Sweetening composition and process therefor
US4122195A (en) * 1977-01-24 1978-10-24 General Foods Corporation Fixation of APM in chewing gum
US4139639A (en) * 1977-01-24 1979-02-13 General Foods Corporation Fixation of APM in chewing gum
US4384004A (en) * 1981-06-02 1983-05-17 Warner-Lambert Company Encapsulated APM and method of preparation
US4384004B1 (fr) * 1981-06-02 1993-06-22 Warner Lambert Co
US4448716A (en) * 1982-03-04 1984-05-15 G. D. Searle & Co. Dipeptide sweetener-metal complexes
WO1985000809A1 (fr) * 1983-08-16 1985-02-28 University Of Georgia Research Foundation, Inc. Synthese de peptides et d'acides amines de cyclopropane

Non-Patent Citations (3)

* Cited by examiner, † Cited by third party
Title
Dissertation University of Georgia, published 1981 Part I Amalogues of Aspartame, Part II Cyclopropyl Amino Acids, Part III the Use of DMAP Tpwards the Synthesis of Dehydro and Cycloproply Peptides, STEPHEN WAYNE KING, 124 pages *
J. Agric. Food Chem., Vol. 32, No. 5, 1984 TADA et al, L-Ornithylaurine, A New Salty Peptide, pages 992-996. *
See also references of EP0205610A4 *

Cited By (21)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0950663A4 (fr) * 1997-08-01 2003-03-19 Toray Industries Stabilisation de proteines utiles et compositions a base de proteines utiles
US10913922B2 (en) 2012-03-30 2021-02-09 Givaudan S.A. N-acylated methionine derivatives as food flavoring compounds
US10201175B2 (en) 2012-03-30 2019-02-12 Givaudan Sa N-acylated 1-aminocycloalkyl carboxylic acids as food flavouring compounds
US11832638B2 (en) 2012-03-30 2023-12-05 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
US10582715B2 (en) 2012-03-30 2020-03-10 Givaudan Sa Powder flavour composition
US10645955B2 (en) 2012-03-30 2020-05-12 Givaudan Sa N-acyl derivatives of gamma amino-butyric acid and beta alanine as food flavouring compounds
US11524933B2 (en) 2012-03-30 2022-12-13 Givaudan Sa In or relating to organic compounds
US10711230B2 (en) 2012-03-30 2020-07-14 Givaudan Sa N-acyl proline derivatives as food flavoring compounds
US11492326B2 (en) 2012-03-30 2022-11-08 Givaudan Sa Organic compounds
US10836712B2 (en) 2012-03-30 2020-11-17 Givaudan S.A. Organic compounds
US11091429B2 (en) 2012-03-30 2021-08-17 Givaudan Sa Organic compounds
US10856563B2 (en) 2012-03-30 2020-12-08 Givaudan S.A. N-acyl-amino acid derivatives for improvement of the flavor profile of edible compositions
US10834943B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds having taste-modifying properties
US10975018B2 (en) 2013-10-02 2021-04-13 Givaudan Sa Organic compounds
US10834951B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US11122826B2 (en) 2013-10-02 2021-09-21 Givaudan Sa Organic compounds
US10834950B2 (en) 2013-10-02 2020-11-17 Givaudan S.A. Organic compounds
US10674755B2 (en) 2013-10-02 2020-06-09 Givaudan S.A. Organic Compounds
US10537127B2 (en) 2013-10-02 2020-01-21 Givaudan S.A. Organic compounds
US11834393B2 (en) 2013-10-02 2023-12-05 Givaudan Sa Organic compounds having taste-modifying properties
CN115160192A (zh) * 2022-08-02 2022-10-11 南通大学 一种2-胍基乙烷-1-磺酸二十八烷基酯、其制备方法及其用途

Also Published As

Publication number Publication date
EP0205610A1 (fr) 1986-12-30
EP0205610A4 (fr) 1988-01-25

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