BE550604A - - Google Patents
Info
- Publication number
- BE550604A BE550604A BE550604DA BE550604A BE 550604 A BE550604 A BE 550604A BE 550604D A BE550604D A BE 550604DA BE 550604 A BE550604 A BE 550604A
- Authority
- BE
- Belgium
- Prior art keywords
- diazo
- oxonorleucine
- acid
- aqueous
- production
- Prior art date
Links
- 239000000243 solution Substances 0.000 claims description 82
- 239000002609 media Substances 0.000 claims description 76
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 69
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 68
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 63
- 238000000034 method Methods 0.000 claims description 59
- 239000000203 mixture Substances 0.000 claims description 45
- 238000006243 chemical reaction Methods 0.000 claims description 44
- MKZFABOMIIHLIT-XUELKZDXSA-N (Z,5S)-5-amino-1-diazonio-6-hydroxy-6-oxohex-1-en-2-olate Chemical compound OC(=O)[C@@H](N)CC\C([O-])=C\[N+]#N MKZFABOMIIHLIT-XUELKZDXSA-N 0.000 claims description 43
- 239000002253 acid Substances 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 40
- -1 diazomethyl group Chemical group 0.000 claims description 40
- 238000004519 manufacturing process Methods 0.000 claims description 34
- 239000011780 sodium chloride Substances 0.000 claims description 31
- 239000003795 chemical substances by application Substances 0.000 claims description 30
- 238000006460 hydrolysis reaction Methods 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 25
- 239000002904 solvent Substances 0.000 claims description 25
- 239000000126 substance Substances 0.000 claims description 25
- 239000003960 organic solvent Substances 0.000 claims description 24
- 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 23
- 150000002148 esters Chemical class 0.000 claims description 21
- FYSNRJHAOHDILO-UHFFFAOYSA-N Thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 20
- 235000015097 nutrients Nutrition 0.000 claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- YXHKONLOYHBTNS-UHFFFAOYSA-N diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 claims description 17
- 239000007788 liquid Substances 0.000 claims description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 16
- 241000187747 Streptomyces Species 0.000 claims description 15
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 14
- SESFRYSPDFLNCH-UHFFFAOYSA-N Benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 13
- 230000001264 neutralization Effects 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 12
- 230000005591 charge neutralization Effects 0.000 claims description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
- 238000006386 neutralization reaction Methods 0.000 claims description 12
- FPWNMEGVZNOPEE-YFKPBYRVSA-N (2S)-2,6-diamino-5-oxohexanoic acid Chemical compound NCC(=O)CC[C@H](N)C(O)=O FPWNMEGVZNOPEE-YFKPBYRVSA-N 0.000 claims description 11
- PNEYBMLMFCGWSK-UHFFFAOYSA-N AI2O3 Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 claims description 11
- 239000012141 concentrate Substances 0.000 claims description 11
- 230000002140 halogenating Effects 0.000 claims description 11
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 11
- 239000011707 mineral Substances 0.000 claims description 11
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 10
- 238000007792 addition Methods 0.000 claims description 10
- 229910052783 alkali metal Inorganic materials 0.000 claims description 10
- 229910052751 metal Inorganic materials 0.000 claims description 10
- 239000002184 metal Substances 0.000 claims description 10
- WQDUMFSSJAZKTM-UHFFFAOYSA-N sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 10
- 230000001476 alcoholic Effects 0.000 claims description 9
- 239000003463 adsorbent Substances 0.000 claims description 8
- 150000001340 alkali metals Chemical class 0.000 claims description 8
- 235000013312 flour Nutrition 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 8
- WCTNRLRGZAAGMK-VKHMYHEASA-N (2S)-2-[(2,2,2-trifluoroacetyl)amino]pentanedioic acid Chemical compound OC(=O)CC[C@@H](C(O)=O)NC(=O)C(F)(F)F WCTNRLRGZAAGMK-VKHMYHEASA-N 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 6
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- WQZGKKKJIJFFOK-VFUOTHLCSA-N β-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 6
- GZCGUPFRVQAUEE-KCDKBNATSA-N D-(+)-Galactose Natural products OC[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O GZCGUPFRVQAUEE-KCDKBNATSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N D-Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- MLCDEEZAJGXKJV-VKHMYHEASA-N N-[(3S)-2,6-dioxooxan-3-yl]-2,2,2-trifluoroacetamide Chemical compound FC(F)(F)C(=O)N[C@H]1CCC(=O)OC1=O MLCDEEZAJGXKJV-VKHMYHEASA-N 0.000 claims description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 claims description 5
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 claims description 5
- 210000002784 Stomach Anatomy 0.000 claims description 5
- 125000005907 alkyl ester group Chemical group 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- 238000005658 halogenation reaction Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229960002989 Glutamic Acid Drugs 0.000 claims description 4
- 240000007842 Glycine max Species 0.000 claims description 4
- 235000010469 Glycine max Nutrition 0.000 claims description 4
- 239000005018 casein Substances 0.000 claims description 4
- 235000021240 caseins Nutrition 0.000 claims description 4
- 238000005984 hydrogenation reaction Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 235000015277 pork Nutrition 0.000 claims description 4
- 235000012424 soybean oil Nutrition 0.000 claims description 4
- 239000003549 soybean oil Substances 0.000 claims description 4
- CEFTXUSFUMNCIW-VKHMYHEASA-N [(3S)-2,6-dioxooxan-3-yl]carbamic acid Chemical compound OC(=O)N[C@H]1CCC(=O)OC1=O CEFTXUSFUMNCIW-VKHMYHEASA-N 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 239000003054 catalyst Substances 0.000 claims description 3
- 235000013922 glutamic acid Nutrition 0.000 claims description 3
- 239000004220 glutamic acid Substances 0.000 claims description 3
- 239000011343 solid material Substances 0.000 claims description 3
- WQZGKKKJIJFFOK-PHYPRBDBSA-N α-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 3
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
- 108010068370 Glutens Proteins 0.000 claims description 2
- 108010070551 Meat Proteins Proteins 0.000 claims description 2
- 239000001888 Peptone Substances 0.000 claims description 2
- 108010080698 Peptones Proteins 0.000 claims description 2
- 240000008529 Triticum aestivum Species 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 239000012531 culture fluid Substances 0.000 claims description 2
- 235000021312 gluten Nutrition 0.000 claims description 2
- 235000019319 peptone Nutrition 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- 235000021307 wheat Nutrition 0.000 claims description 2
- KSIJECNNZVKMJG-YFKPBYRVSA-N (2S)-2-azaniumyl-5-oxohexanoate Chemical compound CC(=O)CC[C@H](N)C(O)=O KSIJECNNZVKMJG-YFKPBYRVSA-N 0.000 claims 3
- 125000004432 carbon atoms Chemical group C* 0.000 claims 3
- 239000003480 eluent Substances 0.000 claims 3
- LQFNXBJWXPAJNJ-YFKPBYRVSA-N (2S)-6-diazo-2-nitrosohexanoic acid Chemical compound OC(=O)[C@@H](N=O)CCCC=[N+]=[N-] LQFNXBJWXPAJNJ-YFKPBYRVSA-N 0.000 claims 2
- JFCQEDHGNNZCLN-UHFFFAOYSA-N Glutaric acid Chemical compound OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 claims 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 claims 2
- 239000001963 growth media Substances 0.000 claims 2
- ARAFEULRMHFMDE-UHFFFAOYSA-N 1,3-oxazolidine-2,5-dione Chemical compound O=C1CNC(=O)O1 ARAFEULRMHFMDE-UHFFFAOYSA-N 0.000 claims 1
- FSFLSXOGQPEFMB-UHFFFAOYSA-N C1(C=2C(C(N1C(C(=O)O)CCC(CN1C(C=3C(C1=O)=CC=CC3)=O)=O)=O)=CC=CC2)=O Chemical compound C1(C=2C(C(N1C(C(=O)O)CCC(CN1C(C=3C(C1=O)=CC=CC3)=O)=O)=O)=CC=CC2)=O FSFLSXOGQPEFMB-UHFFFAOYSA-N 0.000 claims 1
- 241000579977 Volutidae Species 0.000 claims 1
- GPZIHGNYMXVBGP-UHFFFAOYSA-N [N+](=[N-])=CC(CCC1NC(OC1=O)=O)=O Chemical compound [N+](=[N-])=CC(CCC1NC(OC1=O)=O)=O GPZIHGNYMXVBGP-UHFFFAOYSA-N 0.000 claims 1
- SHMREQDSXUSUGA-YFKPBYRVSA-N [N+](=[N-])=CC(CC[C@H](NC(C(F)(F)F)=O)C(=O)O)=O Chemical compound [N+](=[N-])=CC(CC[C@H](NC(C(F)(F)F)=O)C(=O)O)=O SHMREQDSXUSUGA-YFKPBYRVSA-N 0.000 claims 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 claims 1
- 125000000217 alkyl group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003636 chemical group Chemical group 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 229910000510 noble metal Inorganic materials 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 239000003531 protein hydrolysate Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 92
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 description 69
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 40
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000000706 filtrate Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000000855 fermentation Methods 0.000 description 13
- 230000004151 fermentation Effects 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
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- 230000000875 corresponding Effects 0.000 description 11
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 11
- 239000007787 solid Substances 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- YCWQAMGASJSUIP-RXMQYKEDSA-N OC(=O)[C@H](N)CCC(=O)C=[N+]=[N-] Chemical compound OC(=O)[C@H](N)CCC(=O)C=[N+]=[N-] YCWQAMGASJSUIP-RXMQYKEDSA-N 0.000 description 10
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- 230000003287 optical Effects 0.000 description 10
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 10
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- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 10
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N acetic acid ethyl ester Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- WVDDGKGOMKODPV-UHFFFAOYSA-N benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 9
- 150000004292 cyclic ethers Chemical class 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
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- 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 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
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- IOVCWXUNBOPUCH-UHFFFAOYSA-N nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
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- YMWUJEATGCHHMB-UHFFFAOYSA-N methylene dichloride Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
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- GUBGYTABKSRVRQ-YOLKTULGSA-N Maltose Natural products O([C@@H]1[C@H](O)[C@@H](O)[C@H](O)O[C@H]1CO)[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 GUBGYTABKSRVRQ-YOLKTULGSA-N 0.000 description 4
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- VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
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- QDHHCQZDFGDHMP-UHFFFAOYSA-N monochloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 3
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- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- DNZWLJIKNWYXJP-UHFFFAOYSA-N butan-1-ol;propan-2-one Chemical compound CC(C)=O.CCCCO DNZWLJIKNWYXJP-UHFFFAOYSA-N 0.000 description 1
- 210000004027 cells Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-M chloride;hydrate Chemical compound O.[Cl-] DKAGJZJALZXOOV-UHFFFAOYSA-M 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 235000014510 cooky Nutrition 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000005712 crystallization Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 201000008325 diseases of cellular proliferation Diseases 0.000 description 1
- XGZRAKBCYZIBKP-UHFFFAOYSA-L disodium;dihydroxide Chemical compound [OH-].[OH-].[Na+].[Na+] XGZRAKBCYZIBKP-UHFFFAOYSA-L 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 230000002255 enzymatic Effects 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004438 eyesight Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 230000002363 herbicidal Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 235000005772 leucine Nutrition 0.000 description 1
- 150000002614 leucines Chemical class 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- QWIZNVHXZXRPDR-WSCXOGSTSA-N melezitose Chemical compound O([C@@]1(O[C@@H]([C@H]([C@@H]1O[C@@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)O)CO)CO)[C@H]1O[C@H](CO)[C@@H](O)[C@H](O)[C@H]1O QWIZNVHXZXRPDR-WSCXOGSTSA-N 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- GLVAUDGFNGKCSF-UHFFFAOYSA-N mercaptopurine Chemical compound S=C1NC=NC2=C1NC=N2 GLVAUDGFNGKCSF-UHFFFAOYSA-N 0.000 description 1
- 229960001428 mercaptopurine Drugs 0.000 description 1
- KIBVXVWCURWLFD-BYPYZUCNSA-N methyl (2S)-5-chloro-5-oxo-2-[(2,2,2-trifluoroacetyl)amino]pentanoate Chemical class ClC(=O)CC[C@@H](C(=O)OC)NC(=O)C(F)(F)F KIBVXVWCURWLFD-BYPYZUCNSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L mgso4 Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- 230000000813 microbial Effects 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006011 modification reaction Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 230000001613 neoplastic Effects 0.000 description 1
- 230000003472 neutralizing Effects 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 235000019392 nitrosyl chloride Nutrition 0.000 description 1
- 230000001473 noxious Effects 0.000 description 1
- 230000002188 osteogenic Effects 0.000 description 1
- 201000008968 osteosarcoma Diseases 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- UJJLJRQIPMGXEZ-UHFFFAOYSA-M oxolane-2-carboxylate Chemical compound [O-]C(=O)C1CCCO1 UJJLJRQIPMGXEZ-UHFFFAOYSA-M 0.000 description 1
- KHIWWQKSHDUIBK-UHFFFAOYSA-N periodic acid Chemical compound OI(=O)(=O)=O KHIWWQKSHDUIBK-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 230000000885 phytotoxic Effects 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- 229940114148 picric acid Drugs 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000001184 potassium carbonate Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 229940064218 potassium nitrite Drugs 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N precursor Substances N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 238000005086 pumping Methods 0.000 description 1
- 239000003638 reducing agent Substances 0.000 description 1
- 229940120668 salicin Drugs 0.000 description 1
- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000008149 soap solution Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- HHURSJAUVYNJBT-UHFFFAOYSA-M sodium;heptadecyl sulfate Chemical compound [Na+].CCCCCCCCCCCCCCCCCOS([O-])(=O)=O HHURSJAUVYNJBT-UHFFFAOYSA-M 0.000 description 1
- 229960002920 sorbitol Drugs 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 230000002588 toxic Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000001131 transforming Effects 0.000 description 1
- 229950002929 trinitrophenol Drugs 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- DLRVVLDZNNYCBX-ZZFZYMBESA-N β-melibiose 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](O)O1 DLRVVLDZNNYCBX-ZZFZYMBESA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/12—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom
- C07C245/14—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton
- C07C245/18—Diazo compounds, i.e. compounds having the free valencies of >N2 groups attached to the same carbon atom having diazo groups bound to acyclic carbon atoms of a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Biotechnology (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE550604A true BE550604A (ja) |
Family
ID=176427
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE550604D BE550604A (ja) |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE550604A (ja) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965634A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965635A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965637A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965636A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
-
0
- BE BE550604D patent/BE550604A/fr unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2965634A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965635A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965637A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
| US2965636A (en) * | 1958-01-15 | 1960-12-20 | Parke Davis & Co | Norleucine derivatives and process for producing same |
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