SU515461A3 - Способ получени стойких гликопептидных антибиотиков - Google Patents

Способ получени стойких гликопептидных антибиотиков

Info

Publication number: SU515461A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mmkm; absorption; bleomycin; phleomycin; methanol
Prior art date: 1971-08-13

Application number

SU1819085A

Other languages

English (en)

Russian (ru)

Inventor

Юмезава Хамао

Такита Томохисо

Мураока Ясухико

Фудзи Акио

Original Assignee

Зайдан Ходзин Бисейбуцу Кагаку Кенкую Каи (Фирма)

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.)

1971-08-13

Filing date

1972-08-09

Publication date

1976-05-25

1972-08-09 Application filed by Зайдан Ходзин Бисейбуцу Кагаку Кенкую Каи (Фирма) filed Critical Зайдан Ходзин Бисейбуцу Кагаку Кенкую Каи (Фирма)

1976-05-25 Application granted granted Critical

1976-05-25 Publication of SU515461A3 publication Critical patent/SU515461A3/ru

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)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Biochemistry (AREA)
Oncology (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Animal Behavior & Ethology (AREA)
Communicable Diseases (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Peptides Or Proteins (AREA)
Compounds Of Unknown Constitution (AREA)
Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Saccharide Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)

SU1819085A 1971-08-13 1972-08-09 Способ получени стойких гликопептидных антибиотиков SU515461A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP6106371A JPS5337321B2 (de)	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 (de)
AU (1)	AU461403B2 (de)
CA (1)	CA967561A (de)
CH (1)	CH565745A5 (de)
CS (1)	CS168000B2 (de)
DE (1)	DE2239740C3 (de)
DK (1)	DK148482C (de)
FR (1)	FR2150775B1 (de)
GB (1)	GB1345320A (de)
NL (1)	NL150119B (de)
SU (1)	SU515461A3 (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
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 CS CS5595A patent/CS168000B2/cs unknown
- 1972-08-11 NL NL727211052A patent/NL150119B/xx not_active IP Right Cessation
- 1972-08-11 CA CA149,260A patent/CA967561A/en not_active Expired
- 1972-08-11 GB GB3758072A patent/GB1345320A/en not_active Expired
- 1972-08-11 FR FR7229186A patent/FR2150775B1/fr not_active Expired
- 1972-08-11 CH CH1189272A patent/CH565745A5/xx not_active IP Right Cessation
- 1972-08-12 DE DE2239740A patent/DE2239740C3/de not_active Expired

Also Published As

Publication number	Publication date
CA967561A (en)	1975-05-13
CS168000B2 (de)	1976-05-28
NL7211052A (de)	1973-02-15
NL150119B (nl)	1976-07-15
DE2239740C3 (de)	1974-10-17
DE2239740B2 (de)	1974-03-21
DK148482C (da)	1985-12-16
JPS4828401A (de)	1973-04-14
FR2150775A1 (de)	1973-04-13
DK148482B (da)	1985-07-15
JPS5337321B2 (de)	1978-10-07
AU461403B2 (en)	1975-05-22
DE2239740A1 (de)	1973-03-01
FR2150775B1 (de)	1976-04-16
AU4509172A (en)	1974-01-31
GB1345320A (en)	1974-01-30
CH565745A5 (de)	1975-08-29

Publication	Publication Date	Title
Dion et al.	1956	6-Diazo-5-oxo-L-norleucine, a new tumor-inhibitory substance. II. 1 isolation and characterization2
Sato et al.	1978	New antibiotics, aplasmomycins B and C
GB1355260A (en)	1974-06-05	Gentamicin antibiotics
Trown et al.	1963	Biosynthesis of cephalosporin C from amino acids
Wakamiya et al.	1972	Chemical studies on tuberactinomycin. IV. The chemical structure of γ-hydroxy-β-lysine, a new amino acid isolated from tuberactinomycin A and N
US4120955A (en)	1978-10-17	Method for production of kanamycin C and its derivatives
Takita	1959	Studies on purification and properties of phleomycin
FRENCH et al.	1973	Myomycin, a new antibiotic
US4283528A (en)	1981-08-11	1-N-aminohydroxyacyl derivatives of gentamicin B
CA1271744A (en)	1990-07-17	Preparation of aminoglycosides
Varma et al.	1972	Mechanism of the cyanohydrin (Kiliani-Fischer) synthesis
BANNISTER et al.	1992	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)	1979-02-20	Kanamycin C derivatives
MALABARBA et al.	1985	Physico-chemical and biological properties of actagardine and some acid hydrolysis products
Kobayashi et al.	1970	THE SYNTHESIS OF KANAMYCIN-6"-UR0NIC ACID, ITS ESTER AND AMIDE
Omoto et al.	1979	Isolation and structure of Sf-1902 A5 a new globomycin analogue
US2531869A (en)	1950-11-28	Method of recovering and purifying streptomycin
Wolfrom et al.	1963	Thiosugars. II. Rearrangement of 2-(3, 4, 6-Tri-O-acetyl-2-amino-2-deoxy-β-D-glucopyranosyl)-2-thiop seudourea1a, b
GB1345729A (en)	1974-02-06	Recovery and purification of antibiotics
Umezawa et al.	1964	Syntheses of O-(2-amino-2-deoxy-α-D-glucopyranosyl)-deoxystreptamine, an antituberculous isomer of paromamine
Friedman et al.	1963	1-(β-Chloroethyl)-3-carbamylpyridinium Chloride. Prototype of a New Class of Latently Cytotoxic Potential Antitumor Agents1
CA1056824A (en)	1979-06-19	Antibiotic compounds and method of production thereof
SU306669A1 (ru)	1977-10-25	Способ очистки эритромицина
DE2307976B2 (de)	1979-12-06	3-Aminopropylester der Bleomycinsäure, Verfahren zu dessen Herstellung und Verfahren zur Herstellung von Bleomycinsäure
US3821366A (en)	1974-06-28	Antibiotic 19,402 r.p.