SU515461A3 - Способ получени стойких гликопептидных антибиотиков - Google Patents
Способ получени стойких гликопептидных антибиотиковInfo
- Publication number
- SU515461A3 SU515461A3 SU1819085A SU1819085A SU515461A3 SU 515461 A3 SU515461 A3 SU 515461A3 SU 1819085 A SU1819085 A SU 1819085A SU 1819085 A SU1819085 A SU 1819085A SU 515461 A3 SU515461 A3 SU 515461A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- mmkm
- absorption
- bleomycin
- phleomycin
- methanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 12
- 230000002085 persistent effect Effects 0.000 title 1
- 239000003910 polypeptide antibiotic agent Substances 0.000 title 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 22
- 238000010521 absorption reaction Methods 0.000 description 19
- 108010006654 Bleomycin Proteins 0.000 description 12
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 11
- 239000011780 sodium chloride Substances 0.000 description 11
- QRBLKGHRWFGINE-UGWAGOLRSA-N 2-[2-[2-[[2-[[4-[[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[(2r,3s,4s,5s,6s)-3-[(2s,3r,4r,5s)-4-carbamoyl-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)- Chemical compound N=1C(C=2SC=C(N=2)C(N)=O)CSC=1CCNC(=O)C(C(C)=O)NC(=O)C(C)C(O)C(C)NC(=O)C(C(O[C@H]1[C@@]([C@@H](O)[C@H](O)[C@H](CO)O1)(C)O[C@H]1[C@@H]([C@](O)([C@@H](O)C(CO)O1)C(N)=O)O)C=1NC=NC=1)NC(=O)C1=NC(C(CC(N)=O)NCC(N)C(N)=O)=NC(N)=C1C QRBLKGHRWFGINE-UGWAGOLRSA-N 0.000 description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- LTQCLFMNABRKSH-UHFFFAOYSA-N Phleomycin Natural products N=1C(C=2SC=C(N=2)C(N)=O)CSC=1CCNC(=O)C(C(O)C)NC(=O)C(C)C(O)C(C)NC(=O)C(C(OC1C(C(O)C(O)C(CO)O1)OC1C(C(OC(N)=O)C(O)C(CO)O1)O)C=1NC=NC=1)NC(=O)C1=NC(C(CC(N)=O)NCC(N)C(N)=O)=NC(N)=C1C LTQCLFMNABRKSH-UHFFFAOYSA-N 0.000 description 9
- 108010035235 Phleomycins Proteins 0.000 description 9
- 229960001561 bleomycin Drugs 0.000 description 9
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 239000007795 chemical reaction product Substances 0.000 description 6
- 229910052802 copper Inorganic materials 0.000 description 6
- 239000010949 copper Substances 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 5
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 4
- 239000005695 Ammonium acetate Substances 0.000 description 4
- 241000186359 Mycobacterium Species 0.000 description 4
- 229920005654 Sephadex Polymers 0.000 description 4
- 239000012507 Sephadex™ Substances 0.000 description 4
- 238000000862 absorption spectrum Methods 0.000 description 4
- 229940043376 ammonium acetate Drugs 0.000 description 4
- 235000019257 ammonium acetate Nutrition 0.000 description 4
- 230000000845 anti-microbial effect Effects 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000000741 silica gel Substances 0.000 description 3
- 229910002027 silica gel Inorganic materials 0.000 description 3
- DQJCDTNMLBYVAY-ZXXIYAEKSA-N (2S,5R,10R,13R)-16-{[(2R,3S,4R,5R)-3-{[(2S,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5-(ethylamino)-6-hydroxy-2-(hydroxymethyl)oxan-4-yl]oxy}-5-(4-aminobutyl)-10-carbamoyl-2,13-dimethyl-4,7,12,15-tetraoxo-3,6,11,14-tetraazaheptadecan-1-oic acid Chemical compound NCCCC[C@H](C(=O)N[C@@H](C)C(O)=O)NC(=O)CC[C@H](C(N)=O)NC(=O)[C@@H](C)NC(=O)C(C)O[C@@H]1[C@@H](NCC)C(O)O[C@H](CO)[C@H]1O[C@H]1[C@H](NC(C)=O)[C@@H](O)[C@H](O)[C@@H](CO)O1 DQJCDTNMLBYVAY-ZXXIYAEKSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 108010015899 Glycopeptides Proteins 0.000 description 2
- 102000002068 Glycopeptides Human genes 0.000 description 2
- NBLHOLNNKJBEDC-XOGQCRKLSA-N [(2r,3s,4s,5r,6r)-2-[(2r,3s,4s,5s,6s)-2-[(1r,2s)-2-[[6-amino-2-[(1s)-3-amino-1-[[(2s)-2,3-diamino-3-oxopropyl]amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[(2r,3s,4s)-5-[[(2s,3r)-1-[2-[4-[4-[4-(diaminomethylideneamino)butylcarbamoyl]-1,3-th Chemical compound N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCCCN=C(N)N)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1NC=NC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C NBLHOLNNKJBEDC-XOGQCRKLSA-N 0.000 description 2
- NVEXEWYGCXIGOY-UHFFFAOYSA-N [2-[2-[2-[[6-amino-2-[3-amino-1-[(2,3-diamino-3-oxopropyl)amino]-3-oxopropyl]-5-methylpyrimidine-4-carbonyl]amino]-3-[[5-[[1-[2-[4-[4-[4-[[n'-[4-(diaminomethylideneamino)butyl]carbamimidoyl]amino]butylcarbamoyl]-1,3-thiazol-2-yl]-4,5-dihydro-1,3-thiazol-2 Chemical compound N=1C(C=2SC=C(N=2)C(=O)NCCCCNC(N)=NCCCCN=C(N)N)CSC=1CCNC(=O)C(C(O)C)NC(=O)C(C)C(O)C(C)NC(=O)C(C(OC1C(C(O)C(O)C(CO)O1)OC1C(C(OC(N)=O)C(O)C(CO)O1)O)C=1NC=NC=1)NC(=O)C1=NC(C(CC(N)=O)NCC(N)C(N)=O)=NC(N)=C1C NVEXEWYGCXIGOY-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- NBLHOLNNKJBEDC-UHFFFAOYSA-N bleomycin B2 Natural products N=1C(C=2SC=C(N=2)C(=O)NCCCCN=C(N)N)=CSC=1CCNC(=O)C(C(O)C)NC(=O)C(C)C(O)C(C)NC(=O)C(C(OC1C(C(O)C(O)C(CO)O1)OC1C(C(OC(N)=O)C(O)C(CO)O1)O)C=1NC=NC=1)NC(=O)C1=NC(C(CC(N)=O)NCC(N)C(N)=O)=NC(N)=C1C NBLHOLNNKJBEDC-UHFFFAOYSA-N 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 108010065353 phleomycin E Proteins 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000001179 sorption measurement Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- WSNMPAVSZJSIMT-UHFFFAOYSA-N COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 Chemical compound COc1c(C)c2COC(=O)c2c(O)c1CC(O)C1(C)CCC(=O)O1 WSNMPAVSZJSIMT-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000146510 Pereskia bleo Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 229910000365 copper sulfate Inorganic materials 0.000 description 1
- 229910000366 copper(II) sulfate Inorganic materials 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GSWAOPJLTADLTN-UHFFFAOYSA-N oxidanimine Chemical compound [O-][NH3+] GSWAOPJLTADLTN-UHFFFAOYSA-N 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- -1 potassium ferricyanide potassium Chemical compound 0.000 description 1
- UMPKMCDVBZFQOK-UHFFFAOYSA-N potassium;iron(3+);oxygen(2-) Chemical compound [O-2].[O-2].[K+].[Fe+3] UMPKMCDVBZFQOK-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K9/00—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof
- C07K9/001—Peptides having up to 20 amino acids, containing saccharide radicals and having a fully defined sequence; Derivatives thereof the peptide sequence having less than 12 amino acids and not being part of a ring structure
- C07K9/003—Peptides being substituted by heterocyclic radicals, e.g. bleomycin, phleomycin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Biophysics (AREA)
- Communicable Diseases (AREA)
- Biochemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Genetics & Genomics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Compounds Of Unknown Constitution (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP6106371A JPS5337321B2 (enExample) | 1971-08-13 | 1971-08-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU515461A3 true SU515461A3 (ru) | 1976-05-25 |
Family
ID=13160317
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1819085A SU515461A3 (ru) | 1971-08-13 | 1972-08-09 | Способ получени стойких гликопептидных антибиотиков |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5337321B2 (enExample) |
| AU (1) | AU461403B2 (enExample) |
| CA (1) | CA967561A (enExample) |
| CH (1) | CH565745A5 (enExample) |
| CS (1) | CS168000B2 (enExample) |
| DE (1) | DE2239740C3 (enExample) |
| DK (1) | DK148482C (enExample) |
| FR (1) | FR2150775B1 (enExample) |
| GB (1) | GB1345320A (enExample) |
| NL (1) | NL150119B (enExample) |
| SU (1) | SU515461A3 (enExample) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112250737B (zh) * | 2020-10-26 | 2021-11-02 | 北京市农林科学院 | 一种具有排铅功能的毛木耳糖肽及其制备方法与应用 |
-
1971
- 1971-08-13 JP JP6106371A patent/JPS5337321B2/ja not_active Expired
-
1972
- 1972-07-28 AU AU45091/72A patent/AU461403B2/en not_active Expired
- 1972-08-09 SU SU1819085A patent/SU515461A3/ru active
- 1972-08-10 DK DK394472A patent/DK148482C/da active
- 1972-08-11 FR FR7229186A patent/FR2150775B1/fr not_active Expired
- 1972-08-11 CH CH1189272A patent/CH565745A5/xx not_active IP Right Cessation
- 1972-08-11 GB GB3758072A patent/GB1345320A/en not_active Expired
- 1972-08-11 CS CS5595A patent/CS168000B2/cs unknown
- 1972-08-11 CA CA149,260A patent/CA967561A/en not_active Expired
- 1972-08-11 NL NL727211052A patent/NL150119B/xx not_active IP Right Cessation
- 1972-08-12 DE DE2239740A patent/DE2239740C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2150775B1 (enExample) | 1976-04-16 |
| DE2239740B2 (de) | 1974-03-21 |
| DE2239740A1 (de) | 1973-03-01 |
| DE2239740C3 (de) | 1974-10-17 |
| AU4509172A (en) | 1974-01-31 |
| CH565745A5 (enExample) | 1975-08-29 |
| NL7211052A (enExample) | 1973-02-15 |
| NL150119B (nl) | 1976-07-15 |
| JPS4828401A (enExample) | 1973-04-14 |
| CA967561A (en) | 1975-05-13 |
| DK148482B (da) | 1985-07-15 |
| CS168000B2 (enExample) | 1976-05-28 |
| DK148482C (da) | 1985-12-16 |
| JPS5337321B2 (enExample) | 1978-10-07 |
| GB1345320A (en) | 1974-01-30 |
| AU461403B2 (en) | 1975-05-22 |
| FR2150775A1 (enExample) | 1973-04-13 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Dion et al. | 6-Diazo-5-oxo-L-norleucine, A New Tumor-inhibitory Substance. II. 1 Isolation and Characterization2 | |
| Sato et al. | New antibiotics, aplasmomycins B and C | |
| GB1355260A (en) | Gentamicin antibiotics | |
| Trown et al. | Biosynthesis of cephalosporin C from amino acids | |
| SU515461A3 (ru) | Способ получени стойких гликопептидных антибиотиков | |
| US4120955A (en) | Method for production of kanamycin C and its derivatives | |
| Takita | Studies on purification and properties of phleomycin | |
| French et al. | Myomycin, a new antibiotic | |
| DE2364999A1 (de) | Verfahren zur dehydroxylierung von aminoglykosid-antibiotika | |
| US4283528A (en) | 1-N-aminohydroxyacyl derivatives of gentamicin B | |
| Varma et al. | Mechanism of the cyanohydrin (Kiliani-Fischer) synthesis | |
| BANNISTER et al. | Protorubradirin, an antibiotic containing a C-nitroso-sugar fragment, is the true secondary metabolite produced by Streptomyces achromogenes var. rubradiris. Rubradirin, described earlier, is its photo-oxidation product | |
| US4140849A (en) | Kanamycin C derivatives | |
| Dijkstra | Synthesis of 2‐deoxyinosadiamines‐1, 3 including 2‐deoxystreptamine | |
| Suzuki et al. | Studies on a New p-Coumaryl Derivative Isolated from Spinach Leaves: Part I. Its Isolation and Some Physico-chemical Properties Part II. Determination of Chemical Structure | |
| MALABARBA et al. | Physico-chemical and biological properties of actagardine and some acid hydrolysis products | |
| Kobayashi et al. | THE SYNTHESIS OF KANAMYCIN-6"-UR0NIC ACID, ITS ESTER AND AMIDE | |
| Omoto et al. | Isolation and structure of Sf-1902 A5 a new globomycin analogue | |
| US3410867A (en) | Mitomycin derivatives | |
| Wolfrom et al. | Thiosugars. II. Rearrangement of 2-(3, 4, 6-Tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl)-2-thiop seudourea1a, b | |
| GB1345729A (en) | Recovery and purification of antibiotics | |
| Umezawa et al. | Syntheses of O-(2-amino-2-deoxy-α-D-glucopyranosyl)-deoxystreptamine, an antituberculous isomer of paromamine | |
| Schwartzman et al. | Chlortetracycline hydrochloride | |
| CA1056824A (en) | Antibiotic compounds and method of production thereof | |
| US3821366A (en) | Antibiotic 19,402 r.p. |