CS272758B2 - Method of peptide production - Google Patents

Method of peptide production Download PDF

Info

Publication number: CS272758B2
Authority: CS; Czechoslovakia
Prior art keywords: arg; gln; leu; ala; ser
Prior art date: 1983-04-26

Application number

CS20084A

Other languages

Czech (cs)

English (en)

Other versions

CS20084A2 (en

Inventor

Jean E P Rivier

Wylie W Ml Vale

Joachim Spiess

Original Assignee

Salk Inst For Biolog

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.)

1983-04-26

Filing date

1984-01-10

Publication date

1991-02-12

1984-01-10 Application filed by Salk Inst For Biolog filed Critical Salk Inst For Biolog

1990-06-13 Publication of CS20084A2 publication Critical patent/CS20084A2/cs

1991-02-12 Publication of CS272758B2 publication Critical patent/CS272758B2/cs

Links

108090000765 processed proteins & peptides Proteins 0.000 title claims abstract description 129
238000000034 method Methods 0.000 title claims description 38
238000004519 manufacturing process Methods 0.000 title claims description 15
-1 Leu Chemical compound 0.000 claims abstract description 37
DCXYFEDJOCDNAF-REOHCLBHSA-N L-asparagine Chemical group OC(=O)[C@@H](N)CC(N)=O DCXYFEDJOCDNAF-REOHCLBHSA-N 0.000 claims abstract description 23
OUYCCCASQSFEME-MRVPVSSYSA-N D-tyrosine Chemical compound OC(=O)[C@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-MRVPVSSYSA-N 0.000 claims abstract description 21
150000001413 amino acids Chemical class 0.000 claims abstract description 20
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 13
150000003839 salts Chemical class 0.000 claims abstract description 12
230000001817 pituitary effect Effects 0.000 claims abstract description 9
239000001257 hydrogen Substances 0.000 claims abstract description 7
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 7
QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical group C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 claims abstract description 6
HNDVDQJCIGZPNO-RXMQYKEDSA-N D-histidine Chemical compound OC(=O)[C@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-RXMQYKEDSA-N 0.000 claims abstract description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 3
125000006239 protecting group Chemical group 0.000 claims description 64
239000011347 resin Substances 0.000 claims description 61
229920005989 resin Polymers 0.000 claims description 61
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
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108010051696 Growth Hormone Proteins 0.000 claims description 21
239000000122 growth hormone Substances 0.000 claims description 21
235000001014 amino acid Nutrition 0.000 claims description 19
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 18
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims description 15
COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 claims description 11
150000001875 compounds Chemical class 0.000 claims description 11
230000008569 process Effects 0.000 claims description 11
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 claims description 8
KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims description 7
238000003776 cleavage reaction Methods 0.000 claims description 7
229910000040 hydrogen fluoride Inorganic materials 0.000 claims description 7
239000000203 mixture Substances 0.000 claims description 7
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239000002904 solvent Substances 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
FFEARJCKVFRZRR-SCSAIBSYSA-N D-methionine Chemical compound CSCC[C@@H](N)C(O)=O FFEARJCKVFRZRR-SCSAIBSYSA-N 0.000 claims description 5
UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 claims description 4
ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
238000004113 cell culture Methods 0.000 claims description 3
PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 3
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
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DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 2
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ORNDKVCWLUZAQL-FOWIMTFFSA-N rgrf 43 Chemical compound C([C@H](N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CO)C(=O)N[C@@H](CO)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(C)C)C(=O)NCC(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](C)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)NCC(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CC(N)=O)C(O)=O)C1=CN=CN1 ORNDKVCWLUZAQL-FOWIMTFFSA-N 0.000 description 4
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238000001990 intravenous administration Methods 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000002609 medium Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
238000000520 microinjection Methods 0.000 description 1
UBLQIESZTDNNAO-UHFFFAOYSA-N n,n-diethylethanamine;phosphoric acid Chemical compound [O-]P([O-])([O-])=O.CC[NH+](CC)CC.CC[NH+](CC)CC.CC[NH+](CC)CC UBLQIESZTDNNAO-UHFFFAOYSA-N 0.000 description 1
FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
239000010452 phosphate Substances 0.000 description 1
239000011148 porous material Substances 0.000 description 1
230000017363 positive regulation of growth Effects 0.000 description 1
244000144977 poultry Species 0.000 description 1
235000013594 poultry meat Nutrition 0.000 description 1
239000000047 product Substances 0.000 description 1
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
238000003127 radioimmunoassay Methods 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000003248 secreting effect Effects 0.000 description 1
UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
238000010532 solid phase synthesis reaction Methods 0.000 description 1
NHXLMOGPVYXJNR-ATOGVRKGSA-N somatostatin Chemical compound C([C@H]1C(=O)N[C@H](C(N[C@@H](CO)C(=O)N[C@@H](CSSC[C@@H](C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C=CC=CC=2)C(=O)N[C@@H](CC=2C3=CC=CC=C3NC=2)C(=O)N[C@@H](CCCCN)C(=O)N[C@H](C(=O)N1)[C@@H](C)O)NC(=O)CNC(=O)[C@H](C)N)C(O)=O)=O)[C@H](O)C)C1=CC=CC=C1 NHXLMOGPVYXJNR-ATOGVRKGSA-N 0.000 description 1
229960000553 somatostatin Drugs 0.000 description 1
108010036509 somatotropin releasing factor 40 Proteins 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
230000002194 synthesizing effect Effects 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000001131 transforming effect Effects 0.000 description 1
239000003643 water by type Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
239000011701 zinc Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K14/00—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
- C07K14/435—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
- C07K14/575—Hormones
- C07K14/60—Growth hormone-releasing factor [GH-RF], i.e. somatoliberin
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/142—Amino acids; Derivatives thereof
- A23K20/147—Polymeric derivatives, e.g. peptides or proteins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S930/00—Peptide or protein sequence
- Y10S930/01—Peptide or protein sequence
- Y10S930/12—Growth hormone, growth factor other than t-cell or b-cell growth factor, and growth hormone releasing factor; related peptides

Landscapes

Life Sciences & Earth Sciences (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Polymers & Plastics (AREA)
Endocrinology (AREA)
Zoology (AREA)
Organic Chemistry (AREA)
Gastroenterology & Hepatology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biophysics (AREA)
Biochemistry (AREA)
Toxicology (AREA)
Animal Husbandry (AREA)
Engineering & Computer Science (AREA)
Food Science & Technology (AREA)
Peptides Or Proteins (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

CS20084A 1983-04-26 1984-01-10 Method of peptide production CS272758B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/488,748 US4595676A (en)	1983-04-26	1983-04-26	Rat hypothalamic GRF

Publications (2)

Publication Number	Publication Date
CS20084A2 CS20084A2 (en)	1990-06-13
CS272758B2 true CS272758B2 (en)	1991-02-12

Family

ID=23940961

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS20084A CS272758B2 (en)	1983-04-26	1984-01-10	Method of peptide production

Country Status (7)

Country	Link
US (1)	US4595676A (fr)
CA (1)	CA1247601A (fr)
CS (1)	CS272758B2 (fr)
HU (1)	HU199508B (fr)
NZ (1)	NZ207658A (fr)
PH (1)	PH22236A (fr)
SU (1)	SU1477248A3 (fr)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4732972A (en) *	1983-03-07	1988-03-22	Hoffmann-La Roche Inc.	Polypeptides having growth hormone releasing activity
US4689318A (en) *	1985-08-29	1987-08-25	The Salk Institute For Biological Studies	GRF analogs
US4880778A (en) *	1986-05-12	1989-11-14	Eastman Kodak Company	Combinations having synergistic growth hormone releasing activity and methods for use thereof
US5002931A (en) *	1987-05-22	1991-03-26	The Salk Institute For Biological Studies	GRF analogs VII
US4839344A (en) *	1987-06-12	1989-06-13	Eastman Kodak Company	Polypeptide compounds having growth hormone releasing activity
USRE33699E (en) *	1987-07-09	1991-09-24	International Minerals & Chemical Corp.	Growth hormone-releasing factor analogs
US4801456A (en) *	1987-07-09	1989-01-31	International Minerals & Chemical Corp.	Growth hormone-releasing factor analogs
US4880777A (en) *	1987-09-01	1989-11-14	Eastman Kodak Company	Synthetic peptides having growth hormone releasing activity
AU637316B2 (en) *	1988-01-28	1993-05-27	Eastman Kodak Company	Polypeptide compounds having growth hormone releasing activity
US5043322A (en) *	1988-07-22	1991-08-27	The Salk Institute For Biological Studies	Cyclic GRF analogs
US5756458A (en) *	1989-06-16	1998-05-26	Pharmacia & Upjohn Company	Stabilized potent GRF analogs
EP0544706A4 (en) *	1990-06-29	1993-10-13	Hoffmann-La Roche Inc.	Histidine substituted growth hormone releasing factor analogs
EP0490249B1 (fr) *	1990-12-10	1995-03-15	F. Hoffmann-La Roche Ag	Procédé de préparation enzymatique de GRF(1-44)NH2
CA2084061A1 (fr) *	1991-04-09	1992-10-10	Arthur M. Felix	Analogues du facteur liberant l'hormone de croissance
US5246920A (en) *	1992-06-15	1993-09-21	University Of South Florida	Treatment of hyperprolactinemia
US5811074A (en) *	1992-06-29	1998-09-22	University Of South Florida	Method of diagnosing pituitary dependent growth hormone deficiency
BR0206919A (pt) *	2001-02-02	2004-07-06	Conjuchem Inc	Derivados de fator de liberação de hormÈnio de crescimento de longa duração
KR20050071498A (ko) *	2002-09-18	2005-07-07	상트르 오스피딸리에 드 루니버시떼 드 몬트리알	성장 호르몬 방출 호르몬 유사체
US20090088380A1 (en) *	2007-07-12	2009-04-02	Pierrette Gaudreau	Ghrh analogs and therapeutic uses thereof

1983
- 1983-04-26 US US06/488,748 patent/US4595676A/en not_active Expired - Lifetime
1984
- 1984-01-10 CS CS20084A patent/CS272758B2/cs unknown
- 1984-01-12 HU HU8488A patent/HU199508B/hu unknown
- 1984-01-12 SU SU843692330A patent/SU1477248A3/ru active
- 1984-03-22 CA CA000450244A patent/CA1247601A/fr not_active Expired
- 1984-03-27 NZ NZ207658A patent/NZ207658A/xx unknown
- 1984-04-17 PH PH30570A patent/PH22236A/en unknown

Also Published As

Publication number	Publication date
NZ207658A (en)	1988-07-28
CA1247601A (fr)	1988-12-28
HU199508B (en)	1990-02-28
PH22236A (en)	1988-07-01
SU1477248A3 (ru)	1989-04-30
US4595676A (en)	1986-06-17
CS20084A2 (en)	1990-06-13

Publication	Publication Date	Title
FI88402C (fi)	1993-05-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara grf-analoger
US4563352A (en)	1986-01-07	Human pancreatic GRF
FI92210B (fi)	1994-06-30	Menetelmä farmaseuttisesti käyttökelpoisten GRF-analogien valmistamiseksi
US4529595A (en)	1985-07-16	GRF Analogs
FI87080C (fi)	1992-11-25	Foerfarande foer framstaellning av grf-analoger
CS272758B2 (en)	1991-02-12	Method of peptide production
KR0138907B1 (ko)	1998-04-30	합성 펩티드
US5262519A (en)	1993-11-16	GRF analogs XI
US4628043A (en)	1986-12-09	Hypothalamic GRF agonists
JP2758901B2 (ja)	1998-05-28	Ｇｒｆ類似体▲ｖｉｉ▼
FI94356B (fi)	1995-05-15	Menetelmä farmaseuttisesti käyttökelpoisen kasvuhormonia vapauttavan tekijän synteettisen peptidianalogin tai sen ei-myrkyllisen suolan valmistamiseksi
US4703035A (en)	1987-10-27	Human pancreatic GRF amidated fragments
EP0067608A1 (fr)	1982-12-22	CRF et analogues
CS276972B6 (en)	1992-11-18	Peptides, process of their preparation and pharmaceutical containing thereof
CZ3004U1 (cs)	1995-03-03	Peptidy a farmaceutické prostředky s jejich obsahem