CS221284B2 - Method of decreasing the contents of phenylalanine in the proteinous hydrolysates - Google Patents

Method of decreasing the contents of phenylalanine in the proteinous hydrolysates Download PDF

Info

Publication number: CS221284B2
Authority: CS; Czechoslovakia
Prior art keywords: cyclodextrin; phenylalanine; polymer; weight; protein
Prior art date: 1979-12-28

Application number

CS809020A

Other languages

Czech (cs)

English (en)

Inventor

Lajos Szenta

Jozsef Szentli

Manfred Specht

Manfred Rothe

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1979-12-28

Filing date

1980-12-18

Publication date

1983-04-29

1980-12-18 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1983-04-29 Publication of CS221284B2 publication Critical patent/CS221284B2/cs

Links

COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 title claims abstract description 22
COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 title claims abstract description 22
238000000034 method Methods 0.000 title claims description 11
230000003247 decreasing effect Effects 0.000 title 1
229920000642 polymer Polymers 0.000 claims abstract description 24
229920000858 Cyclodextrin Polymers 0.000 claims abstract description 21
239000003531 protein hydrolysate Substances 0.000 claims abstract description 16
108010009736 Protein Hydrolysates Proteins 0.000 claims abstract description 11
239000012141 concentrate Substances 0.000 claims abstract description 8
WHGYBXFWUBPSRW-FOUAGVGXSA-N beta-cyclodextrin Chemical compound OC[C@H]([C@H]([C@@H]([C@H]1O)O)O[C@H]2O[C@@H]([C@@H](O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O[C@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O3)[C@H](O)[C@H]2O)CO)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H]3O[C@@H]1CO WHGYBXFWUBPSRW-FOUAGVGXSA-N 0.000 claims abstract description 7
238000004587 chromatography analysis Methods 0.000 claims abstract description 5
239000001116 FEMA 4028 Substances 0.000 claims abstract description 4
235000011175 beta-cyclodextrine Nutrition 0.000 claims abstract description 4
229960004853 betadex Drugs 0.000 claims abstract description 4
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 claims description 12
239000000203 mixture Substances 0.000 claims description 5
229920002689 polyvinyl acetate Polymers 0.000 claims description 5
239000011118 polyvinyl acetate Substances 0.000 claims description 5
239000004372 Polyvinyl alcohol Substances 0.000 claims description 3
239000000796 flavoring agent Substances 0.000 claims description 3
235000019634 flavors Nutrition 0.000 claims description 3
229920002451 polyvinyl alcohol Polymers 0.000 claims description 3
229920002554 vinyl polymer Polymers 0.000 claims description 3
229920003176 water-insoluble polymer Polymers 0.000 claims description 3
239000004971 Cross linker Substances 0.000 claims description 2
150000001720 carbohydrates Chemical class 0.000 claims description 2
238000004132 cross linking Methods 0.000 claims description 2
229920001577 copolymer Polymers 0.000 claims 1
238000007037 hydroformylation reaction Methods 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
235000001014 amino acid Nutrition 0.000 description 8
150000001413 amino acids Chemical class 0.000 description 6
230000007062 hydrolysis Effects 0.000 description 5
238000006460 hydrolysis reaction Methods 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
-1 tryptophan biphenyls Chemical class 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000013372 meat Nutrition 0.000 description 3
229920005989 resin Polymers 0.000 description 3
239000011347 resin Substances 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
201000011252 Phenylketonuria Diseases 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
238000004458 analytical method Methods 0.000 description 2
230000000536 complexating effect Effects 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000004255 ion exchange chromatography Methods 0.000 description 2
DWKPPFQULDPWHX-VKHMYHEASA-N l-alanyl ester Chemical compound COC(=O)[C@H](C)N DWKPPFQULDPWHX-VKHMYHEASA-N 0.000 description 2
238000002360 preparation method Methods 0.000 description 2
235000018102 proteins Nutrition 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
DEWLEGDTCGBNGU-UHFFFAOYSA-N 1,3-dichloropropan-2-ol Chemical compound ClCC(O)CCl DEWLEGDTCGBNGU-UHFFFAOYSA-N 0.000 description 1
QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 1
XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical class CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
125000004103 aminoalkyl group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
239000012736 aqueous medium Substances 0.000 description 1
229960003237 betaine Drugs 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
XENVCRGQTABGKY-ZHACJKMWSA-N chlorohydrin Chemical compound CC#CC#CC#CC#C\C=C\C(Cl)CO XENVCRGQTABGKY-ZHACJKMWSA-N 0.000 description 1
238000002086 displacement chromatography Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
235000013305 food Nutrition 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002500 ions Chemical group 0.000 description 1
238000002955 isolation Methods 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
210000003041 ligament Anatomy 0.000 description 1
OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
FCTRVTQZOUKUIV-MCDZGGTQSA-M potassium;[[[(2r,3s,4r,5r)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate Chemical compound [K+].C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)([O-])=O)[C@@H](O)[C@H]1O FCTRVTQZOUKUIV-MCDZGGTQSA-M 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000000926 separation method Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23J—PROTEIN COMPOSITIONS FOR FOODSTUFFS; WORKING-UP PROTEINS FOR FOODSTUFFS; PHOSPHATIDE COMPOSITIONS FOR FOODSTUFFS
- A23J3/00—Working-up of proteins for foodstuffs
- A23J3/30—Working-up of proteins for foodstuffs by hydrolysis
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- A61K38/01—Hydrolysed proteins; Derivatives thereof

Landscapes

Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Nutrition Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Pharmacology & Pharmacy (AREA)
General Health & Medical Sciences (AREA)
Immunology (AREA)
Medicinal Chemistry (AREA)
Biochemistry (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Bioinformatics & Cheminformatics (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Coloring Foods And Improving Nutritive Qualities (AREA)
Peptides Or Proteins (AREA)
Polyamides (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Meat, Egg Or Seafood Products (AREA)

CS809020A 1979-12-28 1980-12-18 Method of decreasing the contents of phenylalanine in the proteinous hydrolysates CS221284B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU79CI2001A HU194487B (en)	1979-12-28	1979-12-28	Process for producing food-preparation suitable for feeding sicks of phenylketoneurea from protein hydrolysates

Publications (1)

Publication Number	Publication Date
CS221284B2 true CS221284B2 (en)	1983-04-29

Family

ID=10994784

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS809020A CS221284B2 (en)	1979-12-28	1980-12-18	Method of decreasing the contents of phenylalanine in the proteinous hydrolysates

Country Status (13)

Country	Link
CA (1)	CA1146167A ( )
CH (1)	CH646684A5 ( )
CS (1)	CS221284B2 ( )
DE (1)	DE3049328A1 ( )
DK (1)	DK551180A ( )
ES (1)	ES8200701A1 ( )
FR (1)	FR2472348A1 ( )
GB (1)	GB2066265B ( )
HU (1)	HU194487B ( )
IT (1)	IT1143905B ( )
NO (1)	NO154153C ( )
SE (1)	SE449156B ( )
YU (1)	YU42713B ( )

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU192642B (en) *	1984-12-19	1987-06-29	Forte Fotokemiai Ipar	Process for the extraction of nucleinic acids and purine bases from gelatine
GR861162B (en) *	1985-05-06	1986-09-01	Unilever Nv	Improved protein hydrolysate
FI94088C (fi) *	1992-03-13	1995-07-25	Valio Oy	Menetelmä fenyylialaniinin poistamiseksi proteiinipitoisista koostumuksista

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
IT1096208B (it) *	1978-05-12	1985-08-26	Snam Progetti	Composizione adatta alla riduzione del tenore di fenilalanina e metodo impiegante la stessa

1979
- 1979-12-28 HU HU79CI2001A patent/HU194487B/hu not_active IP Right Cessation
1980
- 1980-12-18 CS CS809020A patent/CS221284B2/cs unknown
- 1980-12-22 CH CH948480A patent/CH646684A5/de not_active IP Right Cessation
- 1980-12-22 SE SE8009070A patent/SE449156B/sv not_active IP Right Cessation
- 1980-12-22 GB GB8041089A patent/GB2066265B/en not_active Expired
- 1980-12-23 DK DK551180A patent/DK551180A/da not_active Application Discontinuation
- 1980-12-23 NO NO803934A patent/NO154153C/no unknown
- 1980-12-23 ES ES498105A patent/ES8200701A1/es not_active Expired
- 1980-12-23 CA CA000367507A patent/CA1146167A/en not_active Expired
- 1980-12-24 IT IT50465/80A patent/IT1143905B/it active
- 1980-12-24 YU YU3260/80A patent/YU42713B/xx unknown
- 1980-12-28 FR FR8027608A patent/FR2472348A1/fr active Granted
- 1980-12-29 DE DE19803049328 patent/DE3049328A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
CH646684A5 (de)	1984-12-14
YU326080A (en)	1984-02-29
GB2066265A (en)	1981-07-08
ES498105A0 (es)	1981-12-01
DK551180A (da)	1981-06-29
ES8200701A1 (es)	1981-12-01
NO154153B (no)	1986-04-21
HU194487B (en)	1988-02-29
IT1143905B (it)	1986-10-29
YU42713B (en)	1988-12-31
IT8050465A0 (it)	1980-12-24
FR2472348B1 ( )	1984-09-07
SE449156B (sv)	1987-04-13
NO154153C (no)	1986-07-30
NO803934L (no)	1981-06-29
FR2472348A1 (fr)	1981-07-03
GB2066265B (en)	1983-04-13
SE8009070L (sv)	1981-06-29
DE3049328A1 (de)	1981-12-03
CA1146167A (en)	1983-05-10

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