PL59518B1 - - Google Patents
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- Publication number
- PL59518B1 PL59518B1 PL117316A PL11731666A PL59518B1 PL 59518 B1 PL59518 B1 PL 59518B1 PL 117316 A PL117316 A PL 117316A PL 11731666 A PL11731666 A PL 11731666A PL 59518 B1 PL59518 B1 PL 59518B1
- Authority
- PL
- Poland
- Prior art keywords
- lysyl
- groups
- protected
- valyl
- cleaved
- Prior art date
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 3
- 229960000258 corticotropin Drugs 0.000 claims description 3
- 238000000034 method Methods 0.000 claims 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 108090000765 processed proteins & peptides Proteins 0.000 claims 3
- 125000006239 protecting group Chemical group 0.000 claims 3
- 125000003277 amino group Chemical group 0.000 claims 2
- 102000004196 processed proteins & peptides Human genes 0.000 claims 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 125000004744 butyloxycarbonyl group Chemical group 0.000 claims 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000000291 glutamic acid group Chemical group N[C@@H](CCC(O)=O)C(=O)* 0.000 claims 1
- 125000000404 glutamine group Chemical group N[C@@H](CCC(N)=O)C(=O)* 0.000 claims 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims 1
- 229920001184 polypeptide Polymers 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 claims 1
- 108010091893 Cosyntropin Proteins 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- ZOEFCCMDUURGSE-SQKVDDBVSA-N cosyntropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 ZOEFCCMDUURGSE-SQKVDDBVSA-N 0.000 description 2
- 229960001423 tetracosactide Drugs 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- 101800000414 Corticotropin Proteins 0.000 description 1
- 102400000739 Corticotropin Human genes 0.000 description 1
- MTCFGRXMJLQNBG-UWTATZPHSA-N D-Serine Chemical compound OC[C@@H](N)C(O)=O MTCFGRXMJLQNBG-UWTATZPHSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- GAPYKZAARZMMGP-UHFFFAOYSA-N pyridin-1-ium;acetate Chemical compound CC(O)=O.C1=CC=NC=C1 GAPYKZAARZMMGP-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Description
Na silikazelu wykazuje on nastepujace warto¬ sci Rf: 50 Rf(43A) = 0,63 Rf(100) = 0,60 Rf (chloroform-metanol = 75:25) = 0,42 55 8)H.D-Ser-Tyr-Ser-Met-Glu-His-Fe-Arg-Try-Gli- -Liz-Pro-Wal-Gli-Liz- Liz- Liz - Liz- Pro -Wal- Liz- -Wal-Tyr-Pro-OH/D-Seri-Liz17.18- fi1'2* - kortikotro- pina). 370 mg chronionej pochodnej tetrakozapeptydu 60 rozpuszcza sie w 7,4 ml 90% kwasu trójfluoroocto- wego i odstawia na 45 minut w temperaturze 25°.Roztwór zageszcza sie nastepnie do okolo 2 ml, rozciencza 20 ml wody, jeszcze raz zageszcza i ostatecznie liofilizuje. Otrzymuje sie trójfluoro- 65 octan wolnego tetrakozapeptydu, który w celu\ 59 518 11 przeprowadzenia w octan rozpuszcza sie w malej ilosci wody i przesacza przez kolumne (0 =12,5 mm; 1 = 15 cm) slabo zasadowego wymieniacza jonowego (na przyklad Merck'a nr II) w postaci octanowej. Eluat zateza sie do okolo 3 ml, liofili- 5 zuje w wysokiej' prózni dodatkowo suszy w tem¬ peraturze 40°. Otrzymuje sie 316 mg chromato¬ graficznie i elektroforetycznie jednolitego octanu D-Ser^Liz17.8, ^-24-kortikotropiny w postaci bia¬ lego, bezpostaciowego proszku. 10 Na chromatogramie cienkowarstwowym na tlen¬ ku glinu w ukladzie 101 zwiazek ten wykazuje wartosc Rf = 0,40 (^1-24-kortikotropina w tych samych warunkach 0,51). Przesuwa sie ona w cza¬ sie elektroforezy (16 obj/cm) przy Ph = 6,1 (bu- 15 for z octanu pirydyny) w ciagu 2 godzin o 8,4 cm w kierunku katody. PL
Claims (1)
1. Sposób wytwarzania nowych peptydów o dzia¬ laniu ACTH, znamienny tym, ze z D-Serylo-Lr -tyrozylo-L-serylo-L-metionylo-Lr-glutamylo-L- -histydylo-L-fenyloalanylo-L^arginylo-L-trypto- 12 fylo-glicylo-Li-lizylo-L-propylo-Lt-walilo-glicylo- -L-lizylo-L-lizylo-L-lizylo-L-lizylo-L-propylo-L- -walilo-L-lizylo- L-walilo- L-tyrozylo- L-proliny lub z odpowiedniego zwiazku, który zamiast reszty glutamylowej posiada reszte glutaminy, w których to peptydach chronione sa co naj¬ mniej grupa a-aminowa i grupy aminowe w lancuchach bocznych jak tez koncowa grupa karboksylowa i grupa karboksylowa ewentu¬ alnie obecna w lancuchu bocznym, odszczepia sie grupy ochronne, po czym otrzymane poli- peptydy przeprowadza sie ewentualnie w ich addycyjne sole z kwasami, lub w estry, ami¬ dy, hydrazydy albo w zwiazki kompleksowe. Sposób wedlug zastrz. 1, znamienny tym, ze grupy ochronne odszczepia sie z peptydu, w którym grupy aminowe chronione sa przez gru¬ pe III-rzed. butylo-oksykarbonylowa, a grupy karboksylowe chronione sa przez grupe III- rzed. butyloestrowa. Sposób wedlug zastrz. 2, znamienny tym, ze grupy ochronne odszczepia sie za pomoca kwa¬ su trójfluorooctowego. Dokonano dwóch poprawek ZG „Ruch" W-wa, zam. 1539-69, nakl. 240 egz. PL
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL59518B1 true PL59518B1 (pl) | 1969-12-29 |
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