SE175013C1 - - Google Patents
Info
- Publication number
- SE175013C1 SE175013C1 SE175013DA SE175013C1 SE 175013 C1 SE175013 C1 SE 175013C1 SE 175013D A SE175013D A SE 175013DA SE 175013 C1 SE175013 C1 SE 175013C1
- Authority
- SE
- Sweden
- Prior art keywords
- diazo
- oxonorleucine
- hydrazine
- solution
- acid
- Prior art date
Links
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 16
- 229910052751 metal Inorganic materials 0.000 claims description 14
- 239000002184 metal Substances 0.000 claims description 14
- YCWQAMGASJSUIP-YFKPBYRVSA-N 6-diazo-5-oxo-L-norleucine Chemical group OC(=O)[C@@H](N)CCC(=O)C=[N+]=[N-] YCWQAMGASJSUIP-YFKPBYRVSA-N 0.000 claims description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- 238000010521 absorption reaction Methods 0.000 claims description 7
- 150000001340 alkali metals Chemical class 0.000 claims description 7
- -1 alkaline earth metal salt Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- LHGVYNDAWRBWGL-UHFFFAOYSA-O (e)-(5-amino-5-carboxy-2-oxopentylidene)-iminoazanium Chemical compound OC(=O)C(N)CCC(=O)C=[N+]=N LHGVYNDAWRBWGL-UHFFFAOYSA-O 0.000 claims description 6
- YCWQAMGASJSUIP-UHFFFAOYSA-N 5-diazo-5-oxo-l-norleucin Chemical compound OC(=O)C(N)CCC(=O)C=[N+]=[N-] YCWQAMGASJSUIP-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 229910052783 alkali metal Inorganic materials 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 230000003287 optical effect Effects 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims description 2
- 150000004703 alkoxides Chemical class 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 239000002689 soil Substances 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 239000000243 solution Substances 0.000 claims 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 9
- 239000007858 starting material Substances 0.000 claims 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 8
- 150000004702 methyl esters Chemical class 0.000 claims 8
- 239000000047 product Substances 0.000 claims 7
- 230000000875 corresponding effect Effects 0.000 claims 5
- 238000006386 neutralization reaction Methods 0.000 claims 4
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- 125000005907 alkyl ester group Chemical group 0.000 claims 3
- 239000000706 filtrate Substances 0.000 claims 3
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- 230000000704 physical effect Effects 0.000 claims 3
- 239000011541 reaction mixture Substances 0.000 claims 3
- 239000005909 Kieselgur Substances 0.000 claims 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000003513 alkali Substances 0.000 claims 2
- 230000004071 biological effect Effects 0.000 claims 2
- 239000002609 medium Substances 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 claims 2
- 238000001179 sorption measurement Methods 0.000 claims 2
- QIWKCQDJZPRXNS-VIFPVBQESA-N (2s)-2-[(2-carboxybenzoyl)amino]pentanedioic acid Chemical class OC(=O)CC[C@@H](C(O)=O)NC(=O)C1=CC=CC=C1C(O)=O QIWKCQDJZPRXNS-VIFPVBQESA-N 0.000 claims 1
- GTVZIRNMBOJOND-YFKPBYRVSA-N (2s)-2-nitrosohexanoic acid Chemical compound CCCC[C@H](N=O)C(O)=O GTVZIRNMBOJOND-YFKPBYRVSA-N 0.000 claims 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims 1
- 150000001408 amides Chemical class 0.000 claims 1
- 150000001413 amino acids Chemical class 0.000 claims 1
- 238000004458 analytical method Methods 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 229930002875 chlorophyll Natural products 0.000 claims 1
- 235000019804 chlorophyll Nutrition 0.000 claims 1
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 150000004292 cyclic ethers Chemical class 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000004108 freeze drying Methods 0.000 claims 1
- 150000002429 hydrazines Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 229910052500 inorganic mineral Inorganic materials 0.000 claims 1
- 239000000463 material Substances 0.000 claims 1
- 239000011707 mineral Substances 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 125000000612 phthaloyl group Chemical group C(C=1C(C(=O)*)=CC=CC1)(=O)* 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 238000001953 recrystallisation Methods 0.000 claims 1
- 230000000630 rising effect Effects 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- YCWQAMGASJSUIP-RXMQYKEDSA-N (2R)-2-azaniumyl-6-diazo-5-oxohexanoate Chemical compound OC(=O)[C@H](N)CCC(=O)C=[N+]=[N-] YCWQAMGASJSUIP-RXMQYKEDSA-N 0.000 description 5
- 201000009030 Carcinoma Diseases 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 206010039491 Sarcoma Diseases 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- 238000000862 absorption spectrum Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- WHUUTDBJXJRKMK-GSVOUGTGSA-N D-glutamic acid Chemical compound OC(=O)[C@H](N)CCC(O)=O WHUUTDBJXJRKMK-GSVOUGTGSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WHUUTDBJXJRKMK-UHFFFAOYSA-N glutamic acid Chemical compound OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 2
- 239000004009 herbicide Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 2
- 150000007523 nucleic acids Chemical class 0.000 description 2
- 102000039446 nucleic acids Human genes 0.000 description 2
- 108020004707 nucleic acids Proteins 0.000 description 2
- 201000008968 osteosarcoma Diseases 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 241001279686 Allium moly Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- 235000009344 Chenopodium album Nutrition 0.000 description 1
- 229930182847 D-glutamic acid Natural products 0.000 description 1
- 241000881853 Galaxias maculatus Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-Glutamic acid Natural products OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241001605685 Nepheronia Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 208000006268 Sarcoma 180 Diseases 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 229910000272 alkali metal oxide Inorganic materials 0.000 description 1
- 239000011260 aqueous acid Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000003139 buffering effect Effects 0.000 description 1
- 208000035269 cancer or benign tumor Diseases 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000008029 eradication Effects 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229960002989 glutamic acid Drugs 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 208000032839 leukemia Diseases 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- 230000000813 microbial effect Effects 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
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- IZRPKIZLIFYYKR-UHFFFAOYSA-N phenyltoloxamine Chemical compound CN(C)CCOC1=CC=CC=C1CC1=CC=CC=C1 IZRPKIZLIFYYKR-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
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 235000015096 spirit Nutrition 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000004018 waxing Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE175013T |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SE175013C1 true SE175013C1 (enrdf_load_html_response) | 1961-01-01 |
Family
ID=41964252
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE175013D SE175013C1 (enrdf_load_html_response) |
Country Status (1)
| Country | Link |
|---|---|
| SE (1) | SE175013C1 (enrdf_load_html_response) |
-
0
- SE SE175013D patent/SE175013C1/sv unknown
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