CS203123B2 - Method of producing 4-hydroxy-l-proline - Google Patents

Method of producing 4-hydroxy-l-proline Download PDF

Info

Publication number: CS203123B2
Authority: CS; Czechoslovakia
Prior art keywords: ion exchanger; resin; solution; acid; item
Prior art date: 1975-05-12

Application number

CS316376A

Other languages

Czech (cs)

English (en)

Inventor

Petrice H Brunet

Original Assignee

Biochim Appl Ind Sa

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.)

1975-05-12

Filing date

1976-05-11

Publication date

1981-02-27

1975-05-12 Priority claimed from FR7514696A external-priority patent/FR2311007A1/fr

1976-03-31 Priority claimed from FR7609288A external-priority patent/FR2346331A2/fr

1976-05-11 Application filed by Biochim Appl Ind Sa filed Critical Biochim Appl Ind Sa

1981-02-27 Publication of CS203123B2 publication Critical patent/CS203123B2/cs

Links

PMMYEEVYMWASQN-DMTCNVIQSA-N Hydroxyproline Chemical compound O[C@H]1CN[C@H](C(O)=O)C1 PMMYEEVYMWASQN-DMTCNVIQSA-N 0.000 title claims abstract description 13
229960002591 hydroxyproline Drugs 0.000 title claims abstract description 10
238000000034 method Methods 0.000 title claims description 69
239000011347 resin Substances 0.000 claims abstract description 22
229920005989 resin Polymers 0.000 claims abstract description 22
235000001014 amino acid Nutrition 0.000 claims abstract description 20
239000007858 starting material Substances 0.000 claims abstract description 20
239000002699 waste material Substances 0.000 claims abstract description 20
150000001413 amino acids Chemical class 0.000 claims abstract description 19
230000002378 acidificating effect Effects 0.000 claims abstract description 15
FGMPLJWBKKVCDB-UHFFFAOYSA-N trans-L-hydroxy-proline Natural products ON1CCCC1C(O)=O FGMPLJWBKKVCDB-UHFFFAOYSA-N 0.000 claims abstract description 10
239000010985 leather Substances 0.000 claims abstract description 5
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 claims abstract description 4
235000003704 aspartic acid Nutrition 0.000 claims abstract description 4
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 claims abstract description 4
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 claims abstract description 3
235000013922 glutamic acid Nutrition 0.000 claims abstract description 3
150000002500 ions Chemical class 0.000 claims description 47
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
239000000203 mixture Substances 0.000 claims description 20
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 18
238000002425 crystallisation Methods 0.000 claims description 12
230000008025 crystallization Effects 0.000 claims description 12
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
102000004190 Enzymes Human genes 0.000 claims description 10
108090000790 Enzymes Proteins 0.000 claims description 10
229910021529 ammonia Inorganic materials 0.000 claims description 10
229940088598 enzyme Drugs 0.000 claims description 10
235000019441 ethanol Nutrition 0.000 claims description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 7
PMMYEEVYMWASQN-UHFFFAOYSA-N dl-hydroxyproline Natural products OC1C[NH2+]C(C([O-])=O)C1 PMMYEEVYMWASQN-UHFFFAOYSA-N 0.000 claims description 7
102000057297 Pepsin A Human genes 0.000 claims description 6
108090000284 Pepsin A Proteins 0.000 claims description 6
229940111202 pepsin Drugs 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 5
102000008186 Collagen Human genes 0.000 claims description 4
108010035532 Collagen Proteins 0.000 claims description 4
108091005804 Peptidases Proteins 0.000 claims description 4
102000035195 Peptidases Human genes 0.000 claims description 4
210000000988 bone and bone Anatomy 0.000 claims description 4
229920001436 collagen Polymers 0.000 claims description 4
230000020477 pH reduction Effects 0.000 claims description 4
239000004925 Acrylic resin Substances 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
108010059712 Pronase Proteins 0.000 claims description 3
238000010828 elution Methods 0.000 claims description 3
OZDAOHVKBFBBMZ-UHFFFAOYSA-N 2-aminopentanedioic acid;hydrate Chemical compound O.OC(=O)C(N)CCC(O)=O OZDAOHVKBFBBMZ-UHFFFAOYSA-N 0.000 claims description 2
108090000631 Trypsin Proteins 0.000 claims description 2
102000004142 Trypsin Human genes 0.000 claims description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
229920001467 poly(styrenesulfonates) Polymers 0.000 claims description 2
229940024999 proteolytic enzymes for treatment of wounds and ulcers Drugs 0.000 claims description 2
150000003335 secondary amines Chemical group 0.000 claims description 2
239000012588 trypsin Substances 0.000 claims description 2
OIEWLITYBUYJOH-UHFFFAOYSA-N 2,3-bis(ethenyl)benzoic acid Chemical compound OC(=O)C1=CC=CC(C=C)=C1C=C OIEWLITYBUYJOH-UHFFFAOYSA-N 0.000 claims 1
KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims 1
239000004793 Polystyrene Substances 0.000 claims 1
101100519432 Rattus norvegicus Pdzd2 gene Proteins 0.000 claims 1
241000187747 Streptomyces Species 0.000 claims 1
241000187392 Streptomyces griseus Species 0.000 claims 1
210000000056 organ Anatomy 0.000 claims 1
229920001568 phenolic resin Polymers 0.000 claims 1
229920002223 polystyrene Polymers 0.000 claims 1
239000003531 protein hydrolysate Substances 0.000 claims 1
239000000463 material Substances 0.000 abstract description 11
238000002360 preparation method Methods 0.000 abstract description 4
235000015277 pork Nutrition 0.000 abstract description 2
229940024606 amino acid Drugs 0.000 abstract 2
NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 abstract 1
241000283690 Bos taurus Species 0.000 abstract 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 abstract 1
239000003957 anion exchange resin Substances 0.000 abstract 1
150000001449 anionic compounds Chemical class 0.000 abstract 1
239000003729 cation exchange resin Substances 0.000 abstract 1
239000004220 glutamic acid Substances 0.000 abstract 1
239000000413 hydrolysate Substances 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
229910001412 inorganic anion Inorganic materials 0.000 abstract 1
239000000243 solution Substances 0.000 description 33
239000000047 product Substances 0.000 description 14
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 12
239000000126 substance Substances 0.000 description 10
230000007062 hydrolysis Effects 0.000 description 8
238000006460 hydrolysis reaction Methods 0.000 description 8
238000002955 isolation Methods 0.000 description 8
108010010803 Gelatin Proteins 0.000 description 7
239000003925 fat Substances 0.000 description 7
229920000159 gelatin Polymers 0.000 description 7
239000008273 gelatin Substances 0.000 description 7
235000019322 gelatine Nutrition 0.000 description 7
235000011852 gelatine desserts Nutrition 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
150000001768 cations Chemical class 0.000 description 6
239000013078 crystal Substances 0.000 description 5
235000018102 proteins Nutrition 0.000 description 5
102000004169 proteins and genes Human genes 0.000 description 5
108090000623 proteins and genes Proteins 0.000 description 5
ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 4
239000004365 Protease Substances 0.000 description 4
235000010633 broth Nutrition 0.000 description 4
239000000872 buffer Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000012452 mother liquor Substances 0.000 description 4
238000005406 washing Methods 0.000 description 4
229920002125 Sokalan® Polymers 0.000 description 3
238000005903 acid hydrolysis reaction Methods 0.000 description 3
150000001298 alcohols Chemical class 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
238000005520 cutting process Methods 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
238000001556 precipitation Methods 0.000 description 3
230000008929 regeneration Effects 0.000 description 3
238000011069 regeneration method Methods 0.000 description 3
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
239000004475 Arginine Substances 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
108090000526 Papain Proteins 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 2
-1 aromatic amino acids Chemical class 0.000 description 2
238000004061 bleaching Methods 0.000 description 2
239000006227 byproduct Substances 0.000 description 2
239000011575 calcium Substances 0.000 description 2
229910052791 calcium Inorganic materials 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
229920001429 chelating resin Polymers 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
238000001914 filtration Methods 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
238000005342 ion exchange Methods 0.000 description 2
229940055729 papain Drugs 0.000 description 2
235000019834 papain Nutrition 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
235000019419 proteases Nutrition 0.000 description 2
239000012460 protein solution Substances 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
238000000926 separation method Methods 0.000 description 2
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
238000003756 stirring Methods 0.000 description 2
DPEYHNFHDIXMNV-UHFFFAOYSA-N (9-amino-3-bicyclo[3.3.1]nonanyl)-(4-benzyl-5-methyl-1,4-diazepan-1-yl)methanone dihydrochloride Chemical compound Cl.Cl.CC1CCN(CCN1Cc1ccccc1)C(=O)C1CC2CCCC(C1)C2N DPEYHNFHDIXMNV-UHFFFAOYSA-N 0.000 description 1
BHPQYMZQTOCNFJ-UHFFFAOYSA-N Calcium cation Chemical compound [Ca+2] BHPQYMZQTOCNFJ-UHFFFAOYSA-N 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000004471 Glycine Substances 0.000 description 1
206010053317 Hydrophobia Diseases 0.000 description 1
ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 description 1
239000004472 Lysine Substances 0.000 description 1
KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
206010037742 Rabies Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
239000002250 absorbent Substances 0.000 description 1
230000002745 absorbent Effects 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
235000004279 alanine Nutrition 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
150000001576 beta-amino acids Chemical class 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
244000240602 cacao Species 0.000 description 1
229910001424 calcium ion Inorganic materials 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000007942 carboxylates Chemical group 0.000 description 1
210000000845 cartilage Anatomy 0.000 description 1
150000001860 citric acid derivatives Chemical class 0.000 description 1
238000004140 cleaning Methods 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
230000009615 deamination Effects 0.000 description 1
238000006481 deamination reaction Methods 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000004042 decolorization Methods 0.000 description 1
230000007812 deficiency Effects 0.000 description 1
238000004821 distillation Methods 0.000 description 1
238000001035 drying Methods 0.000 description 1
235000013861 fat-free Nutrition 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
125000000524 functional group Chemical group 0.000 description 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
210000001156 gastric mucosa Anatomy 0.000 description 1
239000008103 glucose Substances 0.000 description 1
239000001307 helium Substances 0.000 description 1
229910052734 helium Inorganic materials 0.000 description 1
SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
210000004276 hyalin Anatomy 0.000 description 1
229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000002440 industrial waste Substances 0.000 description 1
230000002427 irreversible effect Effects 0.000 description 1
239000004571 lime Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
238000002156 mixing Methods 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
230000009935 nitrosation Effects 0.000 description 1
238000007034 nitrosation reaction Methods 0.000 description 1
210000000496 pancreas Anatomy 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000012071 phase Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920005990 polystyrene resin Polymers 0.000 description 1
238000002203 pretreatment Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
235000013580 sausages Nutrition 0.000 description 1
239000010822 slaughterhouse waste Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000004659 sterilization and disinfection Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
238000000967 suction filtration Methods 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000018553 tannin Nutrition 0.000 description 1
229920001864 tannin Polymers 0.000 description 1
239000001648 tannin Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- 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
- A23J3/32—Working-up of proteins for foodstuffs by hydrolysis using chemical agents
- A23J3/34—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes
- A23J3/341—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes of animal proteins
- A23J3/342—Working-up of proteins for foodstuffs by hydrolysis using chemical agents using enzymes of animal proteins of collagen; of gelatin

Landscapes

Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Nutrition Science (AREA)
General Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Polymers & Plastics (AREA)
Zoology (AREA)
Pyrrole Compounds (AREA)
Peptides Or Proteins (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)

CS316376A 1975-05-12 1976-05-11 Method of producing 4-hydroxy-l-proline CS203123B2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR7514696A FR2311007A1 (fr)	1975-05-12	1975-05-12	Procede de preparation de la 4-hydroxy-l(-)proline
FR7609288A FR2346331A2 (fr)	1976-03-31	1976-03-31	Procede de preparation de la 4-hydroxy-l(-)proline

Publications (1)

Publication Number	Publication Date
CS203123B2 true CS203123B2 (en)	1981-02-27

Family

ID=26218859

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS316376A CS203123B2 (en)	1975-05-12	1976-05-11	Method of producing 4-hydroxy-l-proline

Country Status (6)

Country	Link
BR (1)	BR7602952A (it)
CS (1)	CS203123B2 (it)
DE (1)	DE2620834A1 (it)
ES (1)	ES448035A1 (it)
GB (1)	GB1499086A (it)
IT (1)	IT1059949B (it)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN105837488B (zh) *	2016-03-31	2019-02-15	天津市敬业精细化工有限公司	一种羟脯氨酸发酵生产工艺
CN114105849B (zh) *	2021-12-02	2024-07-09	河北远大九孚生物科技有限公司	一种l-羟基脯氨酸的提取方法

1976
- 1976-04-21 GB GB1606176A patent/GB1499086A/en not_active Expired
- 1976-04-29 IT IT6804876A patent/IT1059949B/it active
- 1976-05-11 CS CS316376A patent/CS203123B2/cs unknown
- 1976-05-11 DE DE19762620834 patent/DE2620834A1/de not_active Withdrawn
- 1976-05-11 BR BR7602952A patent/BR7602952A/pt unknown
- 1976-05-11 ES ES76448035A patent/ES448035A1/es not_active Expired

Also Published As

Publication number	Publication date
ES448035A1 (es)	1977-11-01
BR7602952A (pt)	1976-11-23
DE2620834A1 (de)	1976-11-25
IT1059949B (it)	1982-06-21
GB1499086A (en)	1978-01-25

Publication	Publication Date	Title
US4042576A (en)	1977-08-16	Extraction of glycoproteins and sialic acid from whey
US4100154A (en)	1978-07-11	Process for recovery and separation of nutritious protein hydrolysate and chromium from chrome leather scrap
NZ502015A (en)	2001-11-30	Ion-exchange process for the purification of nutrients from food process streams
JP2622686B2 (ja)	1997-06-18	ｋ−カゼイングリコマクロペプチドの製造法
CA1328950C (en)	1994-04-26	Process for selectively separating the alpha-lactalbumin from the proteins of whey
US7077966B2 (en)	2006-07-18	Process for gelatines extraction and chromium salts recovery from tanned hides and skins shavings
US2386926A (en)	1945-10-16	Separation of amino acids
US2462597A (en)	1949-02-22	Amino acid separation
CS203123B2 (en)	1981-02-27	Method of producing 4-hydroxy-l-proline
US4003992A (en)	1977-01-18	Hydrolytic process for the preparation of amino acids
GB682762A (en)	1952-11-19	Fractionation of amino acid mixtures
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