CA1206057A - Composes siderophoriques - Google Patents

Composes siderophoriques

Info

Publication number: CA1206057A
Authority: CA; Canada
Prior art keywords: composition; siderophoric; insoluble; formula; carrier
Prior art date: 1982-08-20
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

Application number

CA000409869A

Other languages

English (en)

Inventor

Bruce E. Holbein

Irving W. Devoe

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Devoe Holbein International NV

Original Assignee

Devoe Holbein International NV

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.)

1982-08-20

Filing date

1982-08-20

Publication date

1986-06-17

1982-08-20 Application filed by Devoe Holbein International NV filed Critical Devoe Holbein International NV

1982-08-20 Priority to CA000409869A priority Critical patent/CA1206057A/fr

1983-02-24 Priority to US06/469,431 priority patent/US4530963A/en

1983-06-24 Priority to NZ21443983A priority patent/NZ214439A/en

1983-06-24 Priority to NZ204701A priority patent/NZ204701A/en

1983-06-24 Priority to NZ21444083A priority patent/NZ214440A/en

1983-07-05 Priority to AU16560/83A priority patent/AU554842B2/en

1983-07-18 Priority to JP12960483A priority patent/JPS5948085A/ja

1983-07-21 Priority to EP83107137A priority patent/EP0104346A3/fr

1983-07-21 Priority to EP84110501A priority patent/EP0136578A3/fr

1984-06-22 Priority to US06/623,397 priority patent/US4626416A/en

1984-06-28 Priority to US06/625,539 priority patent/US4585559A/en

1984-10-02 Priority to AU33784/84A priority patent/AU568686B2/en

1986-06-17 Application granted granted Critical

1986-06-17 Publication of CA1206057A publication Critical patent/CA1206057A/fr

Status Expired legal-status Critical Current

Links

239000000203 mixture Substances 0.000 title claims abstract description 151
230000000995 siderophoric effect Effects 0.000 title claims description 77
239000000589 Siderophore Substances 0.000 claims abstract description 69
230000000813 microbial effect Effects 0.000 claims abstract description 68
150000001875 compounds Chemical class 0.000 claims abstract description 41
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 claims abstract description 35
239000007788 liquid Substances 0.000 claims abstract description 35
238000000034 method Methods 0.000 claims description 45
108010061075 Enterobactin Proteins 0.000 claims description 19
SERBHKJMVBATSJ-BZSNNMDCSA-N enterobactin Chemical group OC1=CC=CC(C(=O)N[C@@H]2C(OC[C@@H](C(=O)OC[C@@H](C(=O)OC2)NC(=O)C=2C(=C(O)C=CC=2)O)NC(=O)C=2C(=C(O)C=CC=2)O)=O)=C1O SERBHKJMVBATSJ-BZSNNMDCSA-N 0.000 claims description 19
SERBHKJMVBATSJ-UHFFFAOYSA-N Enterobactin Natural products OC1=CC=CC(C(=O)NC2C(OCC(C(=O)OCC(C(=O)OC2)NC(=O)C=2C(=C(O)C=CC=2)O)NC(=O)C=2C(=C(O)C=CC=2)O)=O)=C1O SERBHKJMVBATSJ-UHFFFAOYSA-N 0.000 claims description 18
235000015097 nutrients Nutrition 0.000 claims description 12
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical group OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 7
230000002401 inhibitory effect Effects 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
YCIMNLLNPGFGHC-UHFFFAOYSA-L catecholate(2-) Chemical group [O-]C1=CC=CC=C1[O-] YCIMNLLNPGFGHC-UHFFFAOYSA-L 0.000 claims description 4
239000002738 chelating agent Substances 0.000 claims description 4
150000005206 1,2-dihydroxybenzenes Chemical class 0.000 claims 3
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 abstract description 165
229910052742 iron Inorganic materials 0.000 abstract description 82
229910052751 metal Inorganic materials 0.000 abstract description 14
239000002184 metal Substances 0.000 abstract description 14
150000002894 organic compounds Chemical class 0.000 abstract description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 53
239000002609 medium Substances 0.000 description 37
239000000499 gel Substances 0.000 description 36
239000000243 solution Substances 0.000 description 31
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 24
-1 actinide ions Chemical class 0.000 description 22
229910001868 water Inorganic materials 0.000 description 22
239000011521 glass Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
125000000524 functional group Chemical group 0.000 description 18
229920002401 polyacrylamide Polymers 0.000 description 18
239000000725 suspension Substances 0.000 description 17
239000012153 distilled water Substances 0.000 description 16
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 14
239000002253 acid Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
230000008929 regeneration Effects 0.000 description 12
238000011069 regeneration method Methods 0.000 description 12
UBQYURCVBFRUQT-UHFFFAOYSA-N N-benzoyl-Ferrioxamine B Chemical compound CC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCNC(=O)CCC(=O)N(O)CCCCCN UBQYURCVBFRUQT-UHFFFAOYSA-N 0.000 description 10
239000004809 Teflon Substances 0.000 description 10
229920006362 Teflon® Polymers 0.000 description 10
229940099217 desferal Drugs 0.000 description 10
235000014101 wine Nutrition 0.000 description 10
239000003638 chemical reducing agent Substances 0.000 description 9
238000005859 coupling reaction Methods 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 8
239000000969 carrier Substances 0.000 description 8
230000008878 coupling Effects 0.000 description 8
238000010168 coupling process Methods 0.000 description 8
229940012017 ethylenediamine Drugs 0.000 description 8
239000000741 silica gel Substances 0.000 description 8
229910002027 silica gel Inorganic materials 0.000 description 8
241000894007 species Species 0.000 description 8
229920000936 Agarose Polymers 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
150000002739 metals Chemical class 0.000 description 7
230000008569 process Effects 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
239000011780 sodium chloride Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
NHJVRSWLHSJWIN-UHFFFAOYSA-N 2,4,6-trinitrobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O NHJVRSWLHSJWIN-UHFFFAOYSA-N 0.000 description 6
FALRKNHUBBKYCC-UHFFFAOYSA-N 2-(chloromethyl)pyridine-3-carbonitrile Chemical compound ClCC1=NC=CC=C1C#N FALRKNHUBBKYCC-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
239000003446 ligand Substances 0.000 description 6
238000002156 mixing Methods 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
230000009467 reduction Effects 0.000 description 6
238000006722 reduction reaction Methods 0.000 description 6
239000011734 sodium Substances 0.000 description 6
239000007787 solid Substances 0.000 description 6
125000006850 spacer group Chemical group 0.000 description 6
229940014800 succinic anhydride Drugs 0.000 description 6
230000010736 Chelating Activity Effects 0.000 description 5
239000004677 Nylon Substances 0.000 description 5
230000004913 activation Effects 0.000 description 5
125000003277 amino group Chemical group 0.000 description 5
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
229920001778 nylon Polymers 0.000 description 5
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
229910052778 Plutonium Inorganic materials 0.000 description 4
125000000217 alkyl group Chemical group 0.000 description 4
239000011324 bead Substances 0.000 description 4
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 4
230000015556 catabolic process Effects 0.000 description 4
239000002131 composite material Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
244000005700 microbiome Species 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
229940076400 plutonium Drugs 0.000 description 4
OYEHPCDNVJXUIW-UHFFFAOYSA-N plutonium atom Chemical compound [Pu] OYEHPCDNVJXUIW-UHFFFAOYSA-N 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
YILWWVUXGMGOAM-UHFFFAOYSA-N schizokinen Chemical compound CC(=O)N(O)CCCNC(=O)CC(O)(C(O)=O)CC(=O)NCCCN(O)C(C)=O YILWWVUXGMGOAM-UHFFFAOYSA-N 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000005406 washing Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 3
108010035210 Iron-Binding Proteins Proteins 0.000 description 3
102000008133 Iron-Binding Proteins Human genes 0.000 description 3
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
229960000583 acetic acid Drugs 0.000 description 3
235000010323 ascorbic acid Nutrition 0.000 description 3
238000006149 azo coupling reaction Methods 0.000 description 3
229910021538 borax Inorganic materials 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000001816 cooling Methods 0.000 description 3
239000002537 cosmetic Substances 0.000 description 3
ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 3
229910021645 metal ion Inorganic materials 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
239000000047 product Substances 0.000 description 3
239000012279 sodium borohydride Substances 0.000 description 3
229910000033 sodium borohydride Inorganic materials 0.000 description 3
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 3
239000004328 sodium tetraborate Substances 0.000 description 3
235000010339 sodium tetraborate Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000012360 testing method Methods 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 2
HGDXYCWNFLHQFC-UHFFFAOYSA-N 4-nitrobenzoyl azide Chemical compound [O-][N+](=O)C1=CC=C(C(=O)N=[N+]=[N-])C=C1 HGDXYCWNFLHQFC-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
BPEXJHGGARTCIR-UHFFFAOYSA-N Arthrobactin Chemical compound CC(=O)N(O)CCCCCNC(=O)CC(O)(C(O)=O)CC(=O)NCCCCCN(O)C(C)=O BPEXJHGGARTCIR-UHFFFAOYSA-N 0.000 description 2
YVSLWKNRAQAVTJ-UHFFFAOYSA-N Arthrobactin Natural products CC(=O)C(O)NCCCCNC(=O)CC(O)(CC(=O)NCCCCNC(O)C(=O)C)C(=O)O YVSLWKNRAQAVTJ-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
241000894006 Bacteria Species 0.000 description 2
108010067157 Ferrichrome Proteins 0.000 description 2
229920001503 Glucan Polymers 0.000 description 2
SXRSQZLOMIGNAQ-UHFFFAOYSA-N Glutaraldehyde Chemical compound O=CCCCC=O SXRSQZLOMIGNAQ-UHFFFAOYSA-N 0.000 description 2
229910021578 Iron(III) chloride Inorganic materials 0.000 description 2
150000000994 L-ascorbates Chemical class 0.000 description 2
229930183781 Mycobactin Natural products 0.000 description 2
241000588653 Neisseria Species 0.000 description 2
LCTONWCANYUPML-UHFFFAOYSA-N Pyruvic acid Chemical compound CC(=O)C(O)=O LCTONWCANYUPML-UHFFFAOYSA-N 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
HQYXQBFMMYIDEA-UHFFFAOYSA-N [3-[(1-hydroxy-2-oxoazepan-3-yl)amino]-3-oxopropyl] 7-[formyl(hydroxy)amino]-2-[[2-(2-hydroxyphenyl)-4,5-dihydro-1,3-oxazole-4-carbonyl]amino]heptanoate Chemical compound ON(CCCCCC(NC(=O)C1COC(=N1)c1ccccc1O)C(=O)OCCC(=O)NC1CCCCN(O)C1=O)C=O HQYXQBFMMYIDEA-UHFFFAOYSA-N 0.000 description 2
229910052768 actinide Inorganic materials 0.000 description 2
239000008272 agar Substances 0.000 description 2
125000003368 amide group Chemical group 0.000 description 2
238000005576 amination reaction Methods 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
235000013405 beer Nutrition 0.000 description 2
230000001588 bifunctional effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000872 buffer Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001913 cellulose Substances 0.000 description 2
229920002678 cellulose Polymers 0.000 description 2
239000013522 chelant Substances 0.000 description 2
235000019987 cider Nutrition 0.000 description 2
238000011109 contamination Methods 0.000 description 2
238000006731 degradation reaction Methods 0.000 description 2
125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
239000012954 diazonium Substances 0.000 description 2
150000001989 diazonium salts Chemical class 0.000 description 2
238000006193 diazotization reaction Methods 0.000 description 2
239000003651 drinking water Substances 0.000 description 2
235000020188 drinking water Nutrition 0.000 description 2
238000000605 extraction Methods 0.000 description 2
GGUNGDGGXMHBMJ-UHFFFAOYSA-N ferrichrome Chemical compound [Fe+3].CC(=O)N([O-])CCCC1NC(=O)CNC(=O)CNC(=O)CNC(=O)C(CCCN([O-])C(C)=O)NC(=O)C(CCCN([O-])C(C)=O)NC1=O GGUNGDGGXMHBMJ-UHFFFAOYSA-N 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
235000011389 fruit/vegetable juice Nutrition 0.000 description 2
239000001963 growth medium Substances 0.000 description 2
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230000007062 hydrolysis Effects 0.000 description 2
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230000005764 inhibitory process Effects 0.000 description 2
229910010272 inorganic material Inorganic materials 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
239000007791 liquid phase Substances 0.000 description 2
238000010907 mechanical stirring Methods 0.000 description 2
238000012544 monitoring process Methods 0.000 description 2
229940054534 ophthalmic solution Drugs 0.000 description 2
239000002997 ophthalmic solution Substances 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
229920001343 polytetrafluoroethylene Polymers 0.000 description 2
239000004810 polytetrafluoroethylene Substances 0.000 description 2
239000011148 porous material Substances 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
108090000623 proteins and genes Proteins 0.000 description 2
102000004169 proteins and genes Human genes 0.000 description 2
NYBZAGXTZXPYND-GBIKHYSHSA-N pyochelin I Chemical compound S1C[C@@H](C(O)=O)N(C)[C@H]1[C@@H]1N=C(C=2C(=CC=CC=2)O)SC1 NYBZAGXTZXPYND-GBIKHYSHSA-N 0.000 description 2
238000011084 recovery Methods 0.000 description 2
230000002829 reductive effect Effects 0.000 description 2
PPASLZSBLFJQEF-RKJRWTFHSA-M sodium ascorbate Substances [Na+].OC[C@@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RKJRWTFHSA-M 0.000 description 2
235000010378 sodium ascorbate Nutrition 0.000 description 2
229960005055 sodium ascorbate Drugs 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000011240 wet gel Substances 0.000 description 2
PUWVNTVQJFSBDH-UHFFFAOYSA-N (2S-cis)-N,N'-[(3,6-dioxopiperazine-2,5-diyl)di-3,1-propanediyl]bis[N-hydroxyacetamide] Natural products CC(=O)N(O)CCCC1NC(=O)C(CCCN(O)C(C)=O)NC1=O PUWVNTVQJFSBDH-UHFFFAOYSA-N 0.000 description 1
UGBOUVVZXRMJNM-FUGGEZGHSA-N (2r,3r)-3-[[(2s)-2-amino-6-[[(1s)-5-[(4-amino-4-oxobutanoyl)amino]-8-hydroxy-9-oxo-1,2,3,4-tetrahydropyrimido[1,2-a]quinoline-1-carbonyl]amino]hexanoyl]amino]-2-hydroxy-4-[[(2s)-1-[[(2r,3r)-3-hydroxy-1-[[(2s)-1-[[(3r)-1-hydroxy-2-oxopiperidin-3-yl]amino]- Chemical compound O=C([C@H](C)NC(=O)[C@H](NC(=O)[C@H](C)NC(=O)[C@H](NC(=O)[C@@H](N)CCCCNC(=O)[C@H]1N2C3=CC(=O)C(O)=CC3=CC(NC(=O)CCC(N)=O)=C2NCC1)[C@@H](O)C(O)=O)[C@H](O)C)N[C@@H]1CCCN(O)C1=O UGBOUVVZXRMJNM-FUGGEZGHSA-N 0.000 description 1
BWPMKVHHFNGYEN-CJAUYULYSA-N (4S,5R)-N-[4-[(2,3-dihydroxybenzoyl)amino]butyl]-N-[3-[(2,3-dihydroxybenzoyl)amino]propyl]-2-(2,3-dihydroxyphenyl)-5-methyl-4,5-dihydro-1,3-oxazole-4-carboxamide Chemical compound C[C@H]1OC(=N[C@@H]1C(=O)N(CCCCNC(=O)c1cccc(O)c1O)CCCNC(=O)c1cccc(O)c1O)c1cccc(O)c1O BWPMKVHHFNGYEN-CJAUYULYSA-N 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
WXTMDXOMEHJXQO-UHFFFAOYSA-N 2,5-dihydroxybenzoic acid Chemical group OC(=O)C1=CC(O)=CC=C1O WXTMDXOMEHJXQO-UHFFFAOYSA-N 0.000 description 1
BQQVEASFNMRTBA-UHFFFAOYSA-N 2-[4-(3-aminopropyl)piperazin-1-yl]ethanol Chemical compound NCCCN1CCN(CCO)CC1 BQQVEASFNMRTBA-UHFFFAOYSA-N 0.000 description 1
BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 1
FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 1
MCSXGCZMEPXKIW-UHFFFAOYSA-N 3-hydroxy-4-[(4-methyl-2-nitrophenyl)diazenyl]-N-(3-nitrophenyl)naphthalene-2-carboxamide Chemical compound Cc1ccc(N=Nc2c(O)c(cc3ccccc23)C(=O)Nc2cccc(c2)[N+]([O-])=O)c(c1)[N+]([O-])=O MCSXGCZMEPXKIW-UHFFFAOYSA-N 0.000 description 1
QJZYHAIUNVAGQP-UHFFFAOYSA-N 3-nitrobicyclo[2.2.1]hept-5-ene-2,3-dicarboxylic acid Chemical compound C1C2C=CC1C(C(=O)O)C2(C(O)=O)[N+]([O-])=O QJZYHAIUNVAGQP-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
241000589155 Agrobacterium tumefaciens Species 0.000 description 1
241000589149 Azotobacter vinelandii Species 0.000 description 1
241000194107 Bacillus megaterium Species 0.000 description 1
229910014033 C-OH Inorganic materials 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
102100038916 Caspase-5 Human genes 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
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ODBLHEXUDAPZAU-ZAFYKAAXSA-N D-threo-isocitric acid Chemical compound OC(=O)[C@H](O)[C@@H](C(O)=O)CC(O)=O ODBLHEXUDAPZAU-ZAFYKAAXSA-N 0.000 description 1
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NVVGMIRCFUVBOB-UHFFFAOYSA-N acetic acid;iron Chemical compound [Fe].CC(O)=O NVVGMIRCFUVBOB-UHFFFAOYSA-N 0.000 description 1
150000001255 actinides Chemical class 0.000 description 1
238000005273 aeration Methods 0.000 description 1
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BWPMKVHHFNGYEN-UHFFFAOYSA-N agrobactin Natural products CC1OC(=NC1C(=O)N(CCCCNC(=O)c1cccc(O)c1O)CCCNC(=O)c1cccc(O)c1O)c1cccc(O)c1O BWPMKVHHFNGYEN-UHFFFAOYSA-N 0.000 description 1
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230000000721 bacterilogical effect Effects 0.000 description 1
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230000003115 biocidal effect Effects 0.000 description 1
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238000006073 displacement reaction Methods 0.000 description 1
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125000005843 halogen group Chemical group 0.000 description 1
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150000004677 hydrates Chemical class 0.000 description 1
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INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
238000005342 ion exchange Methods 0.000 description 1
150000002505 iron Chemical class 0.000 description 1
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229940075525 iron chelating agent Drugs 0.000 description 1
LDHBWEYLDHLIBQ-UHFFFAOYSA-M iron(3+);oxygen(2-);hydroxide;hydrate Chemical compound O.[OH-].[O-2].[Fe+3] LDHBWEYLDHLIBQ-UHFFFAOYSA-M 0.000 description 1
FLTRNWIFKITPIO-UHFFFAOYSA-N iron;trihydrate Chemical compound O.O.O.[Fe] FLTRNWIFKITPIO-UHFFFAOYSA-N 0.000 description 1
FZWBNHMXJMCXLU-BLAUPYHCSA-N isomaltotriose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)[C@@H](OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C=O)O1 FZWBNHMXJMCXLU-BLAUPYHCSA-N 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
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238000011068 loading method Methods 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
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239000000463 material Substances 0.000 description 1
235000013372 meat Nutrition 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
238000009629 microbiological culture Methods 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
IJJSYKQZFFGIEE-UHFFFAOYSA-N naphthalene;potassium Chemical compound [K].C1=CC=CC2=CC=CC=C21 IJJSYKQZFFGIEE-UHFFFAOYSA-N 0.000 description 1
229920005615 natural polymer Polymers 0.000 description 1
239000008239 natural water Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
125000004999 nitroaryl group Chemical group 0.000 description 1
235000016709 nutrition Nutrition 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
230000036961 partial effect Effects 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000768 polyamine Polymers 0.000 description 1
239000004417 polycarbonate Substances 0.000 description 1
229920000515 polycarbonate Polymers 0.000 description 1
229920000728 polyester Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001155 polypropylene Polymers 0.000 description 1
229920001282 polysaccharide Polymers 0.000 description 1
239000005017 polysaccharide Substances 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920002635 polyurethane Polymers 0.000 description 1
239000004814 polyurethane Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000019275 potassium ascorbate Nutrition 0.000 description 1
229940017794 potassium ascorbate Drugs 0.000 description 1
HEZHYQDYRPUXNJ-UHFFFAOYSA-L potassium dithionite Chemical compound [K+].[K+].[O-]S(=O)S([O-])=O HEZHYQDYRPUXNJ-UHFFFAOYSA-L 0.000 description 1
CONVKSGEGAVTMB-RXSVEWSESA-M potassium-L-ascorbate Chemical compound [K+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] CONVKSGEGAVTMB-RXSVEWSESA-M 0.000 description 1
238000004321 preservation Methods 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
108010042415 pseudobactin Proteins 0.000 description 1
ZGDFFAWCXJUFOX-UHFFFAOYSA-N pseudobactin Natural products CC(O)C(NC(=O)C(C)NC(=O)C(NC(=O)C(N)CCCCNC(=O)C1CCNC2N1c3cc(O)c(O)cc3C=C2NC(=O)CCC(=O)N)C(O)C(=O)O)C(=O)NC(C)C(=O)NC4CCCN(O)C4=O ZGDFFAWCXJUFOX-UHFFFAOYSA-N 0.000 description 1
108010025281 pyoverdin Proteins 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
230000036647 reaction Effects 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
238000004064 recycling Methods 0.000 description 1
238000009877 rendering Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
239000011369 resultant mixture Substances 0.000 description 1
230000000717 retained effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
PUWVNTVQJFSBDH-RYUDHWBXSA-N rhodotorulic acid Chemical compound CC(=O)N(O)CCC[C@@H]1NC(=O)[C@H](CCCN(O)C(C)=O)NC1=O PUWVNTVQJFSBDH-RYUDHWBXSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
239000001488 sodium phosphate Substances 0.000 description 1
229910000162 sodium phosphate Inorganic materials 0.000 description 1
PPASLZSBLFJQEF-RXSVEWSESA-M sodium-L-ascorbate Chemical compound [Na+].OC[C@H](O)[C@H]1OC(=O)C(O)=C1[O-] PPASLZSBLFJQEF-RXSVEWSESA-M 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
230000035322 succinylation Effects 0.000 description 1
238000010613 succinylation reaction Methods 0.000 description 1
125000000565 sulfonamide group Chemical group 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920005613 synthetic organic polymer Polymers 0.000 description 1
ODBLHEXUDAPZAU-UHFFFAOYSA-N threo-D-isocitric acid Natural products OC(=O)C(O)C(C(O)=O)CC(O)=O ODBLHEXUDAPZAU-UHFFFAOYSA-N 0.000 description 1
239000003104 tissue culture media Substances 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
238000007738 vacuum evaporation Methods 0.000 description 1
239000002699 waste material Substances 0.000 description 1
239000002351 wastewater Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

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Preparation Of Compounds By Using Micro-Organisms (AREA)
Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)

CA000409869A 1982-08-20 1982-08-20 Composes siderophoriques Expired CA1206057A (fr)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
CA000409869A CA1206057A (fr)	1982-08-20	1982-08-20	Composes siderophoriques
US06/469,431 US4530963A (en)	1982-08-20	1983-02-24	Insoluble chelating compositions
NZ21443983A NZ214439A (en)	1982-08-20	1983-06-24	Removal of heavy metal ions from solution
NZ204701A NZ204701A (en)	1982-08-20	1983-06-24	Inhibiting microbial growth in liquid nutrient mediums and insoluble compositions used therein
NZ21444083A NZ214440A (en)	1982-08-20	1983-06-24	The separation of thorium ions from insoluble compositions loaded with thorium and uranium dioxide ions
AU16560/83A AU554842B2 (en)	1982-08-20	1983-07-05	Insoluble chelating compositions
JP12960483A JPS5948085A (ja)	1982-08-20	1983-07-18	不溶性キレ−ト化組成物
EP83107137A EP0104346A3 (fr)	1982-08-20	1983-07-21	Compositions chélatantes insolubles
EP84110501A EP0136578A3 (fr)	1982-08-20	1983-07-21	Séparation du thorium de compositions renfermant du thorium et de l'oxyde d'uranium
US06/623,397 US4626416A (en)	1982-08-20	1984-06-22	Insoluble chelating compositions
US06/625,539 US4585559A (en)	1982-08-20	1984-06-28	Insoluble chelating compositions
AU33784/84A AU568686B2 (en)	1982-08-20	1984-10-02	Separation of thorium ions from an insoluble composition

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CA000409869A CA1206057A (fr)	1982-08-20	1982-08-20	Composes siderophoriques

Publications (1)

Publication Number	Publication Date
CA1206057A true CA1206057A (fr)	1986-06-17

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ID=4123453

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Application Number	Title	Priority Date	Filing Date
CA000409869A Expired CA1206057A (fr)	1982-08-20	1982-08-20	Composes siderophoriques

Country Status (2)

Country	Link
JP (1)	JPS5948085A (fr)
CA (1)	CA1206057A (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113620531A (zh) *	2021-08-19	2021-11-09	北京北控生态建设集团有限公司	一种黑臭水体的修复治理方法

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5249500B2 (ja) *	2005-12-16	2013-07-31	国立大学法人茨城大学	金属イオンの検出方法
JP5439691B2 (ja) *	2007-03-06	2014-03-12	日立化成株式会社	高原子価金属イオンの捕集剤
JP5610410B2 (ja) *	2013-01-28	2014-10-22	国立大学法人茨城大学	高原子価金属イオンの捕集・検出剤

1982
- 1982-08-20 CA CA000409869A patent/CA1206057A/fr not_active Expired
1983
- 1983-07-18 JP JP12960483A patent/JPS5948085A/ja active Pending

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN113620531A (zh) *	2021-08-19	2021-11-09	北京北控生态建设集团有限公司	一种黑臭水体的修复治理方法

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JPS5948085A (ja)	1984-03-19

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Date	Code	Title	Description
2003-06-17	MKEX	Expiry

Publication	Publication Date	Title
US4626416A (en)	1986-12-02	Insoluble chelating compositions
Mohamed et al.	2017	Cytotoxicity and metal ions removal using antibacterial biodegradable hydrogels based on N-quaternized chitosan/poly (acrylic acid)
US3065123A (en)	1962-11-20	Process for control of micro-organisms
BRPI0712162A2 (pt)	2012-01-17	método de fabricação de um complexo de 1,2-benzisotiazolin-3-ona imobilizada/óxido de zinco, o referido complexo, métodos para a proteção de substratos contra infestações microbianas e para a fabricação de um concentrado de dispersão de um complexo de 1,2-benzisotiazolin-3-ona imobilizada/óxido de zinco, composição de 1,2-benzisotiazolin-3-ona ou sais da mesma e uso da referida composição
CN115490341A (zh)	2022-12-20	一种微生物菌剂颗粒、其制备方法及应用
Masheane et al.	2016	Antimicrobial properties of chitosan‐alumina/f‐MWCNT nanocomposites
CN113336870A (zh)	2021-09-03	一种托酚酮-壳聚糖衍生物及其制备方法和应用
WO2017016022A1 (fr)	2017-02-02	Dérivé chito-oligosaccharide-o-acide kojique-base de mannich, agent antibactérien, et son procédé de préparation
Iyengar et al.	1979	Urease bound to chitin with glutaraldehyde
JPH0710390B2 (ja)	1995-02-08	微生物フロックの形成方法
Champagne	2008	The synthesis of water soluble n-acyl chitosan derivatives for characterization as antibacterial agents
CA1215545A (fr)	1986-12-23	Traitement d'une composition insoluble chargee de th.sup.4.sup. et de uo.sup.2.sup. , avec separation de th.sup.4.sup.
JPH06279219A (ja)	1994-10-04	金属イオンとゼオライト化合物による殺菌資材
JPS5948085A (ja)	1984-03-19	不溶性キレ−ト化組成物
US4224411A (en)	1980-09-23	Immobilized aminoacylase
NZ214439A (en)	1987-10-30	Removal of heavy metal ions from solution
JP2001212594A (ja)	2001-08-07	廃水中の硝酸態窒素除去方法
JPH0334905A (ja)	1991-02-14	植物用組成物
US2845448A (en)	1958-07-29	Aromatic sulfonic acid esters of mandelic acid for inhibition of enzymes
US5023332A (en)	1991-06-11	1-methyl-3,5,7-triaza-1-azoniatricyclodecane triiodide
CN110590878B (zh)	2023-03-31	6-噁/噻二唑壳寡糖衍生物及其制备和应用
JPS58186492A (ja)	1983-10-31	活性化ヒドラジンの初期活性を改良する方法
JP2000106870A (ja)	2000-04-18	物質の処理方法および物質の処理剤
CA1211338A (fr)	1986-09-16	Compositions indissolubles
JP2000053514A (ja)	2000-02-22	レジオネラ属細菌が生産する殺菌性物質、これを用いた殺菌剤、水処理剤、スライム抑制剤、及びこれらの製造方法

CA1206057A - Composes siderophoriques - Google Patents

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Priority Applications (12)

Applications Claiming Priority (1)

Publications (1)

Family

ID=4123453

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Cited By (1)

Families Citing this family (3)

Cited By (1)

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