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
  • C07K5/06104—Dipeptides with the first amino acid being acidic
  • C07K5/06113—Asp- or Asn-amino acid
• • A—HUMAN NECESSITIES
  • A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
  • A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • 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 COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
  • A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
  • A23L27/30—Artificial sweetening agents
  • A23L27/31—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives
  • A23L27/32—Artificial sweetening agents containing amino acids, nucleotides, peptides or derivatives containing dipeptides or derivatives

Definitions

• the general Field of the present invention is peptide sweeteners for foods and beverages presently classified in Class 426 and peptide compositions in Class 260.
• a process for sweetening comestibles with low calorie non-toxic edible synthetic sweeteners is also described as well as a novel composition for making such process operable.
• the particular peptide sweeteners illustrated 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 360°F before consumption.
• the sweetener must be at least as sweet as presently known dipeptide sweeteners which are 100-300 times as sweet as an equivalent amount of sucrose.
• the sweetener must be free of aftertaste and capable of admixture with extenders which maintain mouth feel and texture in baked goods to which it has been added.
• the sweetener must be heat stable in cake batters at baking temperatures of the order of 360° F. for 30-45 minutes to maintain sweetness of the baked cake. It cannot degrade or substantially decompose under thermal stress.
• the sweetener must be non-toxic, edible, and substantially free of side reactions to form other products under the influence of heat.
• a number of natural extracts and synthetic compositions have been proposed, tested and evaluated for use as artificial sweeteners over the past 15 years, none have successfully complied with all of the above enumerated requirements.
• Either the particular low calorie sugar substitute suffers the disadvantage of a bitter aftertaste or it exhibits side effects due to chemical modification in vitro, forming upon heating by-products which are no longer sweet and which yield a food product of unsatisfactory taste or texture.
• a chronology of prior artificial sweetener development will serve to frame the relevance of the present discovery.
• the principal object of the present invention is to provide a heat stable low caloric dipeptide sweetening product which can be employed to sweeten cakes and pies and cooked foods and retain its sweetness.
• the composition of the product comprises in admixture a soluble complex of: A.
• a minor amount of weight of a dipeptide of the structure is a major component of the structure of:
• n is a positive integer from 1 to 3
• R is a lower alkyl group of C 3 to C 7 carbon atoms, or a cycloalkyl group of C 3 -C 5 carbons or a lower alkyl substituted cycloalkyl group or a lower alkyl substituted aryl group.
• a preferred R group is one such as n-propyl, isopropyl, n-butyl or isobutyl for high level sweetness, alone or in combination with,
• hydrocolloidal gum is preferably a polysaccharide type hydrocolloidal gum, such as gum tragacanth, gum acacia, pectin, gum karaya, psyIlium seed gum, gum gatti, guar gum, larch gum, and locust bean gum.
• the two components of the complex can be admixed in a number of ratios as long as the gum components exceeds the peptides component.
• the two preferred gums which are gum tragacanth and gum acacia
• the preferred range of proportions of the mixture is a ratio of 1 part by weight of peptide to 5 to 10 parts of hydrocolloidal gum.
• the peptide component itself is also novel, and even without the gum complex, has an unexpected resistance to thermal degradation.
• a baking temperature of 360°F. for 40 minutes only 18% of the dipeptide degrades into D.K.P. (diketopiperazine) and amino acid fragments, while a commercial dipeptide sweetener degrades a a level of about 80% loss of sweetness property after baking under the same conditions.
• Figure 1 of the attached drawing is a schematic representation of synthesis of the new and novel dipeptide as detailed in Example 1.
• the starting amino acids A and B are known compounds.
• the coupling is also well known and is not claimed as part of this invention.
• the preferred complex comprises: a. 10 parts, by weight, of a hydrocolloidal polysaccharide gum selected from gum tragacanth and gum acacia: and b. 1 part, by weight, of a dipeptide of the structural formula:
• R represents a normal propyl group or a normal butyl or isobutyl functional group.
• R represents a normal propyl group or a normal butyl or isobutyl functional group.
• Another preferred product embodiment, or aspect as it is sometimes referred is a novel dipeptide itself of the general formula: wherein R represents a normal propyl group C 3 H 7 or normal butyl or isobutyl groups which makes the ester group larger than a methyl ester earlier shown in the art.
• a third preferred embodiment is a cake mix formula which substitutes the above peptide-gum complex for sucrose in a food composition.
• a fourth preferred embodiment of the invention is a cake mix formula which substitutes the peptide B in concert with other hydrocolloidal polysaccharide gums, such as pectin, for sucrose in the food composition.
• the cycloalkyl alanine component of the new peptide composition is a naturally occurring amino acid which is found in small amounts in fruits such as apples. It is also commercially available from Cal-Biochem Corporation, Los Angeles,
• the aspartic acid component is also commercially available from the same sources.
• hydrocolloidal polysaccharide gums are also 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 to 67, published by John Wiley and Sons, New York.
• the preferred gum component is known to be mixture of acidic polysaccharides containing galacturonic acid, galactose, fucose and xylose and arabinose. It is an exudiate from the Astralagus tree found in Iran, AMD, 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 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 pH to neutral range.
• the propyl, normal butyl or isobutyl ester of the dipeptide aspartic acid cyclopropylalanine is both sweeter than the commercial peptide sweetner aspartic acid phenylalanine, methyl ester, and greatly sweeter than the methyl ester of aspartic acid cyclopropylalanine dipeptide.
• the cyclopropylalanine, n-butyl, isobutyl and propyl esters are stable to heat degradation and other hydrolysis, while the cyclopropyl phenylalanine methyl and cyclopropyl phenylalanine propyl esters are not sweet or stable.
• the amino acid propyl ester is precipitated from the ether solution as the hydrochloride salt (2) upon the addition of anhydrous HCl at 0°C.
• the crystals are collected and recrystallized from ether to provide the product propyl ⁇ - aminocyclopropane carboxylate hydrochloride (2) in purified form.
• the solid salt obtained is dissolved in a 5% sodium bicarbonate solution and the pH adjusted to 5.0.
• the now product as a zwitterion precipitate is collected by filtration and washed in ice cold water. The product is extremely soluble and some water should be evaporated before further filtration. Upon drying the final dipeptide is obtained in 84% yield as a white crystalline solid M P 174-175°C.
• the thermal stability of the molecule is believed to be obtained from the presence of the cyclopropyl "bridge" found in the 1-aminocyclopropane carboxylic acid component of the dipeptide while its relative intensity of sweetness derives from the weight of the alkyl ester group attached to molecule.
• lower alkyl esters of at least 3 carbons in chain length either normal or branched, and either cyclic or acyclic or combinations of the two are believed to result in dipeptides which are both sweet the thermally stable at the temperatures required for cooking and baking of cakes, pies and other foods.
• Example 2-A blend and complex the dipeptide product of Example 1-B with an equivalent amount of gum acacia to obtain a sweetener comples containing a butyl ester rather than a propyl ester of the dipeptide component.
• a cake mix recipe for standard yellow cake taken from page 67 of Chapter 4 of the Better Homes and Gardens Cookbook, 1972, printed by Better Homes and gardens Magazine, New York, New York can be altered to substitute the new sweetener complex of Example 2-A for the sugar ingredient of the recipe.
• the new cake formula hence is as follows:
• 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 moderate speed until it is fluffy.
• the dry ingredients, cake flour, sodium bicarbonate, and salt are also mixed and sifted. They are then added slowly to the creamed mixture in several equal amounts with intermittent addition of whole milk and beating for 3 minutes after each addition. Beat the entire mixture as a dough briskly for about 1-2 minutes. Place the doughy batter into a pie greased and lightly floured 9 x 11 ⁇ 2 inch round cake pan and place into an oven pie heated to a bake temperature of 350°F.
• Example 3-B In a manner similar to Example 3-A, one can prepare a cake formula by substituting the sweetener component of either Example 1-A, 1-B or 2-B in equal amount for the sweetener from Example 2-A referred to therein to obtain a satisfactory sweet tasting cake food product.
• confectionary products such as hard candies have been prepared as examples of other sweet tasting food products.
• Example 2 Repeat the procedure for Examples 2 and 3, except to substitute in Example 2, 90 parts by weight of gum tragacanth (a water soluble hydrocolloidal polysaccharide gum) for gum acacia of Example 2.
• the complex will maintain its sweet character during the baking of the cake as in Example 3.
• the manner and the desirable result will be the same.
• the edible sweeteners of the present invention are particularly useful as heat stable sweeteners for baking pies and cakes, breads, and other foods which must be heated to temperatures of the order of 350-360°F
• the edible sweeteners of the present invention are particularly useful as stabilized sweeteners for fruit juices, fruit preparations, canned vegetables and fruits, dairy products such as egg products, milk drinks, ice cream, syrups, chocolate syrups and bars, candy, icing and dessert toppings, meat products and especially carbonated and non-carbonated beverages.
• R in the general structure indicates that lower alkyl groups, such as, normal or isopropyl or butyl or isobutyl groups are preferred, other alkyl functions as well as amine functions, sulfate and sulfonate salts and alkaryl groups, such as benzyl, may be considered as modifications which may still further stabilize the peptide or increase its sweetening effects. These can be considered functional equivalents

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• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Proteomics, Peptides & Aminoacids (AREA)
• Health & Medical Sciences (AREA)
• Organic Chemistry (AREA)
• Nutrition Science (AREA)
• Engineering & Computer Science (AREA)
• Food Science & Technology (AREA)
• Polymers & Plastics (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)

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• 1985
  • 1985-12-11 JP JP61500336A patent/JPS63500211A/ja active Pending
  • 1985-12-11 WO PCT/US1985/002422 patent/WO1986003378A1/en not_active Application Discontinuation
  • 1985-12-11 EP EP19860900456 patent/EP0204826A4/de not_active Withdrawn
• 1986
  • 1986-08-11 SE SE8603380A patent/SE8603380D0/xx unknown

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