PL52610B1 - - Google Patents
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- PL52610B1 PL52610B1 PL104208A PL10420864A PL52610B1 PL 52610 B1 PL52610 B1 PL 52610B1 PL 104208 A PL104208 A PL 104208A PL 10420864 A PL10420864 A PL 10420864A PL 52610 B1 PL52610 B1 PL 52610B1
- Authority
- PL
- Poland
- Prior art keywords
- chp
- cys
- che
- conh
- pro
- Prior art date
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- 238000000034 method Methods 0.000 claims description 9
- 229920001184 polypeptide Polymers 0.000 claims description 6
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 3
- 239000007800 oxidant agent Substances 0.000 claims 3
- 239000007864 aqueous solution Substances 0.000 claims 2
- KVPHTGVUMJGMCX-BIIVOSGPSA-N Asp-Cys-Pro Chemical compound C1C[C@@H](N(C1)C(=O)[C@H](CS)NC(=O)[C@H](CC(=O)O)N)C(=O)O KVPHTGVUMJGMCX-BIIVOSGPSA-N 0.000 claims 1
- DSTWKJOBKSMVCV-UWVGGRQHSA-N Cys-Tyr Chemical compound SC[C@H](N)C(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 DSTWKJOBKSMVCV-UWVGGRQHSA-N 0.000 claims 1
- FYYSIASRLDJUNP-WHFBIAKZSA-N Glu-Asp Chemical compound OC(=O)CC[C@H](N)C(=O)N[C@@H](CC(O)=O)C(O)=O FYYSIASRLDJUNP-WHFBIAKZSA-N 0.000 claims 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 claims 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 1
- 108010069495 cysteinyltyrosine Proteins 0.000 claims 1
- 108010063718 gamma-glutamylaspartic acid Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 238000007254 oxidation reaction Methods 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 238000005868 electrolysis reaction Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-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 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- QIVBCDIJIAJPQS-VIFPVBQESA-N L-tryptophane Chemical compound C1=CC=C2C(C[C@H](N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-VIFPVBQESA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-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
- 150000001413 amino acids Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000001174 ascending effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- QJTUONIWKBEBCB-UHFFFAOYSA-N butan-2-one;pyridine Chemical compound CCC(C)=O.C1=CC=NC=C1 QJTUONIWKBEBCB-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000004816 paper chromatography Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000012266 salt solution Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Description
e) Amid L-cysteinylo-L-tyrozylo-L-fenyloalanilo-L- glutaminylo-L-asparaginylo- L -cysteinylo- L -proli- lo-L-ornitylo-glicyny.Roztwór 5 g amidu N-karbobenzoksy-S-benzylo-L- cysteinylo- L -tyrozylo- L -fenaloalanilo- L -gluta- minylo- L -asparaginylo- S -benzylo- L -cysteinylo- L-prolilo-N-<5-p-toluenousulfonylo- L-ornitylo-glicy- ny w 1200 ml cieklego amoniaku zadaje sie pod¬ czas mieszania w temperaturze wrzenia taka iloscia metalicznego sodu lub potasu, az wystapi trwale nie¬ bieskie zabarwienie. Po dodaniu 3 g chlorku amono¬ wego odparowuje sie roztwór do sucha. Pozostalosc zawiera amid L-cysteinylo-L-tyrozylo-L-fenyloala- nilo- L -giutaminylo- L -asparaginylo- L -cysteiny- lo-L-prolilo-L-ornitylo-glicyny. f) Polipeptyd o wzorze 1.Pozostalosc otrzymana wedlug przykladu I e) roz¬ puszcza sie w 5 litrach 0,01 n kwasu octowego i utle¬ nia sie przy wartosci pH 6,5 8,0 przez wprowadzenie powietrza lub tlenu w ciagu 1 godziny przy tempe¬ raturze 0°—40°. Roztwór zawierajacy substancje zakwasza sie do osiagniecia wartosci pH 4,0—5,0 i po dodaniu 50 g chlorku sodowego lub 0,64 g kwa¬ su metanosulfonowego odparowuje do sucha. Otrzy¬ muje sie suchy proszek o dobrej trwalosci, który mozna przechowywac; Rozpuszcza sie on tworzac klarowny roztwór zwiazku polipeptydowego we- 5 dlug wzoru 1. Mozna jednak roztwór zwiazku poli¬ peptydowego wedlug wzoru 1 stosowac bezposred¬ nio, ewentualnie po rozcienczeniu woda lub roz¬ tworem soli kuchennej w celu uzyskania roztworu izbtonicznego. Przy pomocy chromatografii bibu- io lowej i elektrolizy bibulowej okazalo sie, ze zwiazek o wzorze 1 jest jednorodny. Wartosc Rf dla chro- matogramu wstepujacego (butanol) kwas octowy lodowaty (woda 70:10:20 wynosi 0,05; (metyloetylo- keton (pirydyna) woda 65:15 :20 wyriósi 0,12. Przy 1B wysokojakosciowej elektrolizie bibulowej polipeptyd o wzorze 1 migruje przy wartosci pH 5,8 (pirydyna) kwas octowy lodowaty (woda 9:1:90/7/10 drogi histydyny (E° = 0,7 His); a przy wartosci pH 1,9 5 o (kwas mrówkowy) kwas octowy lodowaty (woda 15 : 20 :10 : 75) 9/10 drogi tryptofanu (E.° = 0,9 Try).Przy calkowitej hydrolizie za pomoca 6 n kwasu solnego podczas 16 godzin w temperaturze 110° bez dostepu powietrza otrzymano mieszanine amino¬ kwasów w obliczonym stosunku ilosciowym. 25 Przyklad II. Postepuje sie analogicznie jak w przykladzie I, utlenia jednak polipeptyd o wzo¬ rze 5 na koncu w temperaturze 0—40° przez dodanie 7,5 ml 1 n roztworu nadtlenku wodoru w roztworze wodnym przy pH 4,0—9,0. 30 PL
Claims (5)
- Zastrzezenia patentowe 1. Sposób wytwarzania nowego polipeptydu o wzo¬ rze 1, znamienny tym, ze nonapeptyd o wzorze 5 utlenia sie w roztworze wodnym przy wartosci pH = 4^-9.
- 2. Sposób wedlug zastrz. 1, znamienny tym, ze utlenianie prowadzi sie w roztworze wodnym za- 40 wierajacym rozpuszczalnik organiczny.
- 3. Sposób wedlug zastrz. 1, 2, znamienny tym, ze jako srodek utleniajacy stosuje sie powietrze.
- 4. Sposób wedlug zastrz. 1, 2, znamienny tym, ze jako srodek utleniajacy stosuje sie tlen. 45
- 5. Sposób wedlug zastrz. 1, 2, znamienny tym, ze jako srodek utleniajacy stosuje sie nadtlenek wo¬ doru. 35KI. 12 q, 6/01 52610 MKP C 07 c COMH. C6H40H C6H5 CH,, C0UH2 CH£ CH CH& CH2 MH„-CH-CO-NH-tH-CO-NH-CH-C0-NH-CH-C0-NH-CH-CÓ-NH-0H-CO ZI I CH, \ ' S - Cys Tyn F e/i Giu Asp I Cys CH,_CH? CH? I c CH? i c CHp i CH? N —CH-CO-NH-CH-CO-WH-CM -CONH- Pro Om Gli W«r« 4 COMH- I ' CHP CHE CONH; l ' CHE S-R' I CH2 CH2iHa I CHp NHR CHP ! C CH2 Cl-U NH2-CH-C0-NH-CH-.CO-NH^CH-C0-N CH-CO-NH-CH-CO-WH-CH -CONH, OLU Asp Cys Pro Onn Gli Wzór £KI. 12 q, 6/01 52610 MKP C 07 c S-R1 C6H»0H CgHe i lu I CH- CH^ CHp R"_NH-C.H-CO-NH-CH-CO-NH-CH-.CQ-OH Cys Ty» Pen VJxór3 CONH2 S-R' C6H4OH C6H^ CH& C0NH2 S-R» CHp ^^2 CHp ¦" CHo "2 ^^2 R"-NH-CH-C0-MH-Ch-C0-NH-CH-C0_WH-CH-C0-WH-CH-C0-NH-CH-CO. C/s Tyir* Pen GLu Asp C-ys NHRU 1 CHo 1 c CH2-CH2 CH2 I CH2 CHe l—N — CH-CO-MH-CH-CO-NH-CH -C0NH2 Pro Orn GL u WZOr TKI. 12 q, 6/01 52610 MKP C 07 c CONH, I L SH C6M^0H CgH^ CH2 CQMHa SH CHo CH? CH, CH3 CHp CH3 i i I * I d i I NH2-CH-CÓ-NH-CH-C0-NH-CH-CO-NH-CH-CO-NH-CH-CO-NH-CH-C0- Cya Vyr Fen Glu. ftsp cys I * CH? i fc l ^ i c II2 I M — CH-CO-^H-CH-CO-NK-CH -C0WH3 Pro Orn GIL \/zor 5KI. 12 q, 6/01 52610 MKP C 07 c C6H^OH C6H5 CH; C0NH- l 4 i c CONH, '2 CH2 CH2 -"p NH--CH-C0-NH-CH-C0-NH-CH-C0_NH-CH-C0-tJH-CH-C0-NH-CH-CO- *I l 1 ' S I 6 Cys Tyr fen Olu. A&p Cys CH2 -CH2 LN Riin CH-C0-MH-CH-C0-'NH-CH--C0NH2 Pro ©Li W*or o Wok 6 a e b 1 6 o=i ~R"»V~ ~^| ¦^CH2-CH2-CH2-CHE-NH2 _CH2-CHE~CHa-NH-C-NHa NH -CHi-CH2-CH2^H2 X I | Liz 1 Ar$ 1 Om PL
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL52610B1 true PL52610B1 (pl) | 1966-12-25 |
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