GB1532181A - Pentapetides and a method of preparing them - Google Patents
Pentapetides and a method of preparing themInfo
- Publication number
- GB1532181A GB1532181A GB2435/77A GB243577A GB1532181A GB 1532181 A GB1532181 A GB 1532181A GB 2435/77 A GB2435/77 A GB 2435/77A GB 243577 A GB243577 A GB 243577A GB 1532181 A GB1532181 A GB 1532181A
- Authority
- GB
- United Kingdom
- Prior art keywords
- boc
- ala
- gly
- pentapeptides
- condensation
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- QNAYBMKLOCPYGJ-UWTATZPHSA-N D-alanine Chemical compound C[C@@H](N)C(O)=O QNAYBMKLOCPYGJ-UWTATZPHSA-N 0.000 abstract 5
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 abstract 4
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 abstract 4
- 230000005494 condensation Effects 0.000 abstract 3
- 238000009833 condensation Methods 0.000 abstract 3
- QNAYBMKLOCPYGJ-UHFFFAOYSA-N D-alpha-Ala Natural products CC([NH3+])C([O-])=O QNAYBMKLOCPYGJ-UHFFFAOYSA-N 0.000 abstract 2
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 abstract 2
- 229940024606 amino acid Drugs 0.000 abstract 2
- 150000001413 amino acids Chemical class 0.000 abstract 2
- 229960004441 tyrosine Drugs 0.000 abstract 2
- QVHJQCGUWFKTSE-RXMQYKEDSA-N (2r)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-RXMQYKEDSA-N 0.000 abstract 1
- ZYJPUMXJBDHSIF-NSHDSACASA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=CC=C1 ZYJPUMXJBDHSIF-NSHDSACASA-N 0.000 abstract 1
- IMUSLIHRIYOHEV-ZETCQYMHSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-methylsulfanylbutanoic acid Chemical compound CSCC[C@@H](C(O)=O)NC(=O)OC(C)(C)C IMUSLIHRIYOHEV-ZETCQYMHSA-N 0.000 abstract 1
- QVHJQCGUWFKTSE-YFKPBYRVSA-N (2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)OC(C)(C)C QVHJQCGUWFKTSE-YFKPBYRVSA-N 0.000 abstract 1
- CNBUSIJNWNXLQQ-NSHDSACASA-N (2s)-3-(4-hydroxyphenyl)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid Chemical compound CC(C)(C)OC(=O)N[C@H](C(O)=O)CC1=CC=C(O)C=C1 CNBUSIJNWNXLQQ-NSHDSACASA-N 0.000 abstract 1
- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 abstract 1
- -1 Ala Chemical compound 0.000 abstract 1
- 239000004471 Glycine Substances 0.000 abstract 1
- FFEARJCKVFRZRR-UHFFFAOYSA-N L-Methionine Natural products CSCCC(N)C(O)=O FFEARJCKVFRZRR-UHFFFAOYSA-N 0.000 abstract 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 abstract 1
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 abstract 1
- 229930195722 L-methionine Natural products 0.000 abstract 1
- 229960003767 alanine Drugs 0.000 abstract 1
- 238000004873 anchoring Methods 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 229960004452 methionine Drugs 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 229960005190 phenylalanine Drugs 0.000 abstract 1
- 229920001184 polypeptide Polymers 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 102000004196 processed proteins & peptides Human genes 0.000 abstract 1
- 108090000765 processed proteins & peptides Proteins 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 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
- C07K14/665—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
- C07K14/70—Enkephalins
- C07K14/702—Enkephalins with at least 1 amino acid in D-form
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Biochemistry (AREA)
- Genetics & Genomics (AREA)
- Gastroenterology & Hepatology (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Zoology (AREA)
- Toxicology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Biophysics (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
1532181 Pentapeptides BECKMAN INSTRUMENTS Inc 21 Jan 1977 [2 Feb 1976 8 April 1976] 02435/77 Heading C3H A pentapeptide of the formula wherein X is Gly, Ala, D-Ala provided that, if Y is OH, X is Ala or D-Ala, may be prepared by anchoring the carboxyl group of L-methionine to a solid support, and sequential condensation of L-phenylalanine; glycine; an amino acid selected from glycine, D-alanine and L-alanine; and L-tyrosine, to produce a pentapeptide chain bonded to said support, wherein the amino acids are N- protected and the N-protective group is removed after each condensation, and wherein the L-tyrosine carries a protected hydroxyl group; and deprotecting and cleaving said polypeptide from said support. In the Examples, BHA resin is condensed with (N-deprotection after each condensation), (i) Boc-Met-OH, (ii) Boc-Phe-OH, (iii) Boc-Gly- OH, (iv) Boc-Gly-OH, Boc-Ala-OH or Boc-DAla-OH, (v) Boc-Tyr(OBrZ)-OH, and the pentapeptides are cleaved and deprotected to yield H-Tyr-X<SP>1</SP>-Gly-Phe-Met-NH 2 wherein X<SP>1</SP> is Gly, Ala, D-Ala. Medicinal compositions, preferably in the form of powders or solutions, comprise the pentapeptides in admixture with a pharmaceutically-acceptable carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/654,641 US4212797A (en) | 1976-02-02 | 1976-02-02 | Synthetic pentapeptide having opiate agonist activity |
| US67500376A | 1976-04-08 | 1976-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1532181A true GB1532181A (en) | 1978-11-15 |
Family
ID=27096788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2435/77A Expired GB1532181A (en) | 1976-02-02 | 1977-01-21 | Pentapetides and a method of preparing them |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JPS5295632A (en) |
| DE (1) | DE2703121A1 (en) |
| GB (1) | GB1532181A (en) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7709806L (en) * | 1976-09-01 | 1978-03-02 | Coy David Howard | PROCEDURE FOR PREPARING PEPTIDES |
| HU178001B (en) * | 1976-09-16 | 1982-02-28 | Gyogyszekutato Intezet | Process for preparing new pentapeptides with morphine-like activity and derivatives thereof |
| US4259234A (en) * | 1976-09-27 | 1981-03-31 | Eli Lilly And Company | Analgesic compounds |
| US4264491A (en) * | 1977-10-03 | 1981-04-28 | Eli Lilly And Company | Analgesic compounds |
-
1977
- 1977-01-21 GB GB2435/77A patent/GB1532181A/en not_active Expired
- 1977-01-26 DE DE19772703121 patent/DE2703121A1/en not_active Withdrawn
- 1977-02-01 JP JP931277A patent/JPS5295632A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE2703121A1 (en) | 1977-08-04 |
| JPS5295632A (en) | 1977-08-11 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |