CS257766B2 - Method of cyclic peptide's a-21978c derivative preparation - Google Patents
Method of cyclic peptide's a-21978c derivative preparation Download PDFInfo
- Publication number
- CS257766B2 CS257766B2 CS833607A CS360783A CS257766B2 CS 257766 B2 CS257766 B2 CS 257766B2 CS 833607 A CS833607 A CS 833607A CS 360783 A CS360783 A CS 360783A CS 257766 B2 CS257766 B2 CS 257766B2
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- CS
- Czechoslovakia
- Prior art keywords
- formula
- compound
- снз
- core
- acid
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- 238000000034 method Methods 0.000 title claims description 50
- 238000002360 preparation method Methods 0.000 title claims description 39
- 108010069514 Cyclic Peptides Proteins 0.000 title claims description 18
- 102000001189 Cyclic Peptides Human genes 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 80
- -1 8-methyldecanoyl Chemical group 0.000 claims description 46
- 125000006239 protecting group Chemical group 0.000 claims description 31
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 28
- 238000006243 chemical reaction Methods 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000002252 acyl group Chemical group 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 239000007858 starting material Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 108090000765 processed proteins & peptides Proteins 0.000 claims description 6
- 125000003342 alkenyl group Chemical group 0.000 claims description 5
- 102000004196 processed proteins & peptides Human genes 0.000 claims description 4
- 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 4
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 52
- 229910001868 water Inorganic materials 0.000 description 46
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
- 239000002609 medium Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 32
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
- 239000002904 solvent Substances 0.000 description 20
- 229960000583 acetic acid Drugs 0.000 description 19
- 238000004128 high performance liquid chromatography Methods 0.000 description 18
- 239000002262 Schiff base Substances 0.000 description 17
- 150000004753 Schiff bases Chemical class 0.000 description 17
- 239000000047 product Substances 0.000 description 17
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000002253 acid Chemical class 0.000 description 15
- 238000005917 acylation reaction Methods 0.000 description 15
- 238000005947 deacylation reaction Methods 0.000 description 15
- 230000020176 deacylation Effects 0.000 description 14
- YGPSJZOEDVAXAB-UHFFFAOYSA-N (R)-Kynurenine Natural products OC(=O)C(N)CC(=O)C1=CC=CC=C1N YGPSJZOEDVAXAB-UHFFFAOYSA-N 0.000 description 13
- 230000010933 acylation Effects 0.000 description 13
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- 125000001589 carboacyl group Chemical group 0.000 description 12
- 244000005700 microbiome Species 0.000 description 11
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- 241000187840 Actinoplanes utahensis Species 0.000 description 10
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000000741 silica gel Substances 0.000 description 10
- 229910002027 silica gel Inorganic materials 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- AHLPHDHHMVZTML-UHFFFAOYSA-N Orn-delta-NH2 Natural products NCCCC(N)C(O)=O AHLPHDHHMVZTML-UHFFFAOYSA-N 0.000 description 9
- UTJLXEIPEHZYQJ-UHFFFAOYSA-N Ornithine Natural products OC(=O)C(C)CCCN UTJLXEIPEHZYQJ-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000010828 elution Methods 0.000 description 9
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- AHLPHDHHMVZTML-BYPYZUCNSA-N L-Ornithine Chemical compound NCCC[C@H](N)C(O)=O AHLPHDHHMVZTML-BYPYZUCNSA-N 0.000 description 8
- 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 8
- QIVBCDIJIAJPQS-UHFFFAOYSA-N Tryptophan Natural products C1=CC=C2C(CC(N)C(O)=O)=CNC2=C1 QIVBCDIJIAJPQS-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 8
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- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 7
- 125000003277 amino group Chemical group 0.000 description 7
- 239000002585 base Substances 0.000 description 7
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- 238000000746 purification Methods 0.000 description 7
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- 239000008272 agar Substances 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 230000000844 anti-bacterial effect Effects 0.000 description 6
- 238000003556 assay Methods 0.000 description 6
- 230000003115 biocidal effect Effects 0.000 description 6
- 239000008367 deionised water Substances 0.000 description 6
- 229910021641 deionized water Inorganic materials 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000013587 production medium Substances 0.000 description 6
- 238000006722 reduction reaction Methods 0.000 description 6
- 230000001954 sterilising effect Effects 0.000 description 6
- 238000004659 sterilization and disinfection Methods 0.000 description 6
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 6
- 108090000790 Enzymes Proteins 0.000 description 5
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- 239000003242 anti bacterial agent Substances 0.000 description 5
- 230000002441 reversible effect Effects 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- CDAZRCDEDLQYTI-UHFFFAOYSA-N (2,4,5-trichlorophenyl) decanoate Chemical compound CCCCCCCCCC(=O)OC1=CC(Cl)=C(Cl)C=C1Cl CDAZRCDEDLQYTI-UHFFFAOYSA-N 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000011707 mineral Substances 0.000 description 4
- NUJGJRNETVAIRJ-UHFFFAOYSA-N octanal Chemical compound CCCCCCCC=O NUJGJRNETVAIRJ-UHFFFAOYSA-N 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000000825 ultraviolet detection Methods 0.000 description 4
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 4
- LHJGJYXLEPZJPM-UHFFFAOYSA-N 2,4,5-trichlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C=C1Cl LHJGJYXLEPZJPM-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 238000000862 absorption spectrum Methods 0.000 description 3
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- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
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Classifications
-
- 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
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38201282A | 1982-05-21 | 1982-05-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CS360783A2 CS360783A2 (en) | 1987-09-17 |
| CS257766B2 true CS257766B2 (en) | 1988-06-15 |
Family
ID=23507203
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS833607A CS257766B2 (en) | 1982-05-21 | 1983-05-20 | Method of cyclic peptide's a-21978c derivative preparation |
Country Status (15)
| Country | Link |
|---|---|
| KR (1) | KR860002194B1 (de) |
| AT (1) | AT402299B (de) |
| BG (1) | BG40657A3 (de) |
| CA (1) | CA1216579A (de) |
| CS (1) | CS257766B2 (de) |
| DD (1) | DD210257A5 (de) |
| DK (1) | DK221183A (de) |
| EG (1) | EG16044A (de) |
| ES (1) | ES522562A0 (de) |
| FI (1) | FI79118C (de) |
| GR (1) | GR78851B (de) |
| HU (1) | HU193039B (de) |
| PL (1) | PL142112B1 (de) |
| PT (1) | PT76703B (de) |
| RO (1) | RO86722B (de) |
-
1983
- 1983-05-13 CA CA000428101A patent/CA1216579A/en not_active Expired
- 1983-05-16 RO RO110958A patent/RO86722B/ro unknown
- 1983-05-16 PT PT76703A patent/PT76703B/pt unknown
- 1983-05-16 AT AT0178583A patent/AT402299B/de not_active IP Right Cessation
- 1983-05-18 FI FI831756A patent/FI79118C/fi not_active IP Right Cessation
- 1983-05-18 DK DK221183A patent/DK221183A/da not_active Application Discontinuation
- 1983-05-18 EG EG298/83A patent/EG16044A/xx active
- 1983-05-19 ES ES522562A patent/ES522562A0/es active Granted
- 1983-05-19 GR GR78851A patent/GR78851B/el unknown
- 1983-05-19 BG BG061022A patent/BG40657A3/xx unknown
- 1983-05-19 KR KR1019830002224A patent/KR860002194B1/ko not_active Expired
- 1983-05-20 DD DD83251128A patent/DD210257A5/de unknown
- 1983-05-20 HU HU831796A patent/HU193039B/hu unknown
- 1983-05-20 PL PL1983242098A patent/PL142112B1/pl unknown
- 1983-05-20 CS CS833607A patent/CS257766B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA1216579A (en) | 1987-01-13 |
| EG16044A (en) | 1991-03-30 |
| AT402299B (de) | 1997-03-25 |
| PT76703A (en) | 1983-06-01 |
| DK221183D0 (da) | 1983-05-18 |
| ATA178583A (de) | 1996-08-15 |
| KR840005078A (ko) | 1984-11-03 |
| FI79118B (fi) | 1989-07-31 |
| DK221183A (da) | 1983-11-22 |
| RO86722A (ro) | 1985-04-17 |
| CS360783A2 (en) | 1987-09-17 |
| KR860002194B1 (ko) | 1986-12-30 |
| ES8502081A1 (es) | 1984-12-16 |
| HU193039B (en) | 1987-08-28 |
| DD210257A5 (de) | 1984-06-06 |
| ES522562A0 (es) | 1984-12-16 |
| FI831756L (fi) | 1983-11-22 |
| PL142112B1 (en) | 1987-09-30 |
| GR78851B (de) | 1984-10-02 |
| FI79118C (fi) | 1989-11-10 |
| FI831756A0 (fi) | 1983-05-18 |
| PT76703B (pt) | 1986-03-27 |
| BG40657A3 (en) | 1987-01-15 |
| PL242098A1 (en) | 1984-07-02 |
| RO86722B (ro) | 1985-05-01 |
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