CH626891A5 - - Google Patents
Download PDFInfo
- Publication number
- CH626891A5 CH626891A5 CH898276A CH898276A CH626891A5 CH 626891 A5 CH626891 A5 CH 626891A5 CH 898276 A CH898276 A CH 898276A CH 898276 A CH898276 A CH 898276A CH 626891 A5 CH626891 A5 CH 626891A5
- Authority
- CH
- Switzerland
- Prior art keywords
- adenine
- adenosine
- water
- nicotinamide
- nad
- Prior art date
Links
- BAWFJGJZGIEFAR-NNYOXOHSSA-N NAD zwitterion Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-N 0.000 claims description 36
- 229950006238 nadide Drugs 0.000 claims description 32
- 229930027945 nicotinamide-adenine dinucleotide Natural products 0.000 claims description 30
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 28
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 claims description 24
- GFFGJBXGBJISGV-UHFFFAOYSA-N adenyl group Chemical class N1=CN=C2N=CNC2=C1N GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims description 24
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000005515 coenzyme Substances 0.000 claims description 13
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 12
- 229960005305 adenosine Drugs 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 10
- 230000002255 enzymatic effect Effects 0.000 claims description 9
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 claims description 8
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 claims description 8
- ZKHQWZAMYRWXGA-UHFFFAOYSA-N Adenosine triphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(=O)OP(O)(O)=O)C(O)C1O ZKHQWZAMYRWXGA-UHFFFAOYSA-N 0.000 claims description 8
- 229910019142 PO4 Inorganic materials 0.000 claims description 8
- 229960000643 adenine Drugs 0.000 claims description 8
- 229920002521 macromolecule Polymers 0.000 claims description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 8
- 239000010452 phosphate Substances 0.000 claims description 8
- 229930024421 Adenine Natural products 0.000 claims description 7
- 102000004190 Enzymes Human genes 0.000 claims description 7
- 108090000790 Enzymes Proteins 0.000 claims description 7
- UDMBCSSLTHHNCD-KQYNXXCUSA-N adenosine 5'-monophosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O UDMBCSSLTHHNCD-KQYNXXCUSA-N 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- UDMBCSSLTHHNCD-UHFFFAOYSA-N Coenzym Q(11) Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(O)=O)C(O)C1O UDMBCSSLTHHNCD-UHFFFAOYSA-N 0.000 claims description 5
- LNQVTSROQXJCDD-UHFFFAOYSA-N adenosine monophosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(CO)C(OP(O)(O)=O)C1O LNQVTSROQXJCDD-UHFFFAOYSA-N 0.000 claims description 5
- ZKHQWZAMYRWXGA-KQYNXXCUSA-J ATP(4-) Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-J 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- 238000001042 affinity chromatography Methods 0.000 claims description 4
- 150000001718 carbodiimides Chemical class 0.000 claims description 4
- 229920002401 polyacrylamide Polymers 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 3
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 239000006185 dispersion Substances 0.000 claims description 2
- 238000006911 enzymatic reaction Methods 0.000 claims description 2
- 239000000835 fiber Substances 0.000 claims description 2
- 239000003094 microcapsule Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- ZKHQWZAMYRWXGA-KQYNXXCUSA-N Adenosine triphosphate Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O ZKHQWZAMYRWXGA-KQYNXXCUSA-N 0.000 claims 4
- XJLXINKUBYWONI-NNYOXOHSSA-O NADP(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-NNYOXOHSSA-O 0.000 claims 4
- 229960001456 adenosine triphosphate Drugs 0.000 claims 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- BAWFJGJZGIEFAR-NNYOXOHSSA-O NAD(+) Chemical compound NC(=O)C1=CC=C[N+]([C@H]2[C@@H]([C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 BAWFJGJZGIEFAR-NNYOXOHSSA-O 0.000 claims 3
- 229960003190 adenosine monophosphate Drugs 0.000 claims 3
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 239000002184 metal Substances 0.000 claims 2
- 239000003880 polar aprotic solvent Substances 0.000 claims 2
- 238000007306 functionalization reaction Methods 0.000 claims 1
- 230000026030 halogenation Effects 0.000 claims 1
- 238000005658 halogenation reaction Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 22
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- XJLXINKUBYWONI-DQQFMEOOSA-N [[(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-3-hydroxy-4-phosphonooxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [(2s,3r,4s,5s)-5-(3-carbamoylpyridin-1-ium-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphate Chemical compound NC(=O)C1=CC=C[N+]([C@@H]2[C@H]([C@@H](O)[C@H](COP([O-])(=O)OP(O)(=O)OC[C@@H]3[C@H]([C@@H](OP(O)(O)=O)[C@@H](O3)N3C4=NC=NC(N)=C4N=C3)O)O2)O)=C1 XJLXINKUBYWONI-DQQFMEOOSA-N 0.000 description 10
- 239000011780 sodium chloride Substances 0.000 description 10
- 238000003756 stirring Methods 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CEJGRWLFSMJKIT-UHFFFAOYSA-N 3-[(6-amino-7h-purin-8-yl)sulfanyl]propanoic acid;pyridine-3-carboxamide Chemical compound NC(=O)C1=CC=CN=C1.NC1=NC=NC2=C1NC(SCCC(O)=O)=N2 CEJGRWLFSMJKIT-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 6
- 229920002873 Polyethylenimine Polymers 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000008351 acetate buffer Substances 0.000 description 6
- -1 for example Chemical class 0.000 description 6
- 239000000499 gel Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 102000007698 Alcohol dehydrogenase Human genes 0.000 description 5
- 108010021809 Alcohol dehydrogenase Proteins 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- DKIDEFUBRARXTE-UHFFFAOYSA-N 3-mercaptopropanoic acid Chemical compound OC(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-N 0.000 description 4
- 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 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000007983 Tris buffer Substances 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- 230000008033 biological extinction Effects 0.000 description 4
- 229940021019 disal Drugs 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 238000002798 spectrophotometry method Methods 0.000 description 4
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 3
- 108020005199 Dehydrogenases Proteins 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 238000010908 decantation Methods 0.000 description 3
- 238000000502 dialysis Methods 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 235000011180 diphosphates Nutrition 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 229960003966 nicotinamide Drugs 0.000 description 3
- 235000005152 nicotinamide Nutrition 0.000 description 3
- 239000011570 nicotinamide Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 3
- 238000002211 ultraviolet spectrum Methods 0.000 description 3
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- 102100031126 6-phosphogluconolactonase Human genes 0.000 description 2
- 108010029731 6-phosphogluconolactonase Proteins 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
- 108010018962 Glucosephosphate Dehydrogenase Proteins 0.000 description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002684 Sepharose Polymers 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000005119 centrifugation Methods 0.000 description 2
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 2
- 238000001962 electrophoresis Methods 0.000 description 2
- 239000003480 eluent Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- DCPMPXBYPZGNDC-UHFFFAOYSA-N hydron;methanediimine;chloride Chemical compound Cl.N=C=N DCPMPXBYPZGNDC-UHFFFAOYSA-N 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 description 2
- 239000000741 silica gel Substances 0.000 description 2
- 229910002027 silica gel Inorganic materials 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 238000012800 visualization Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WFIYPADYPQQLNN-UHFFFAOYSA-N 2-[2-(4-bromopyrazol-1-yl)ethyl]isoindole-1,3-dione Chemical compound C1=C(Br)C=NN1CCN1C(=O)C2=CC=CC=C2C1=O WFIYPADYPQQLNN-UHFFFAOYSA-N 0.000 description 1
- SFENEGWBRXYBJT-UHFFFAOYSA-N 2-methylpropanoic acid;hydrate Chemical compound O.CC(C)C(O)=O SFENEGWBRXYBJT-UHFFFAOYSA-N 0.000 description 1
- UQADZBSCNRWCBX-JJNLEZRASA-N 3-[6-amino-9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]sulfanylpropanoic acid Chemical compound OC(=O)CCSC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O UQADZBSCNRWCBX-JJNLEZRASA-N 0.000 description 1
- 102000004567 6-phosphogluconate dehydrogenase Human genes 0.000 description 1
- 108020001657 6-phosphogluconate dehydrogenase Proteins 0.000 description 1
- VJUPMOPLUQHMLE-UUOKFMHZSA-N 8-Bromoadenosine Chemical compound BrC1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O VJUPMOPLUQHMLE-UUOKFMHZSA-N 0.000 description 1
- MSSXOMSJDRHRMC-UHFFFAOYSA-N 9H-purine-2,6-diamine Chemical class NC1=NC(N)=C2NC=NC2=N1 MSSXOMSJDRHRMC-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- NBSCHQHZLSJFNQ-GASJEMHNSA-N D-Glucose 6-phosphate Chemical compound OC1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O NBSCHQHZLSJFNQ-GASJEMHNSA-N 0.000 description 1
- 101710088194 Dehydrogenase Proteins 0.000 description 1
- VFRROHXSMXFLSN-UHFFFAOYSA-N Glc6P Natural products OP(=O)(O)OCC(O)C(O)C(O)C(O)C=O VFRROHXSMXFLSN-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 229930195714 L-glutamate Natural products 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- 229910019065 NaOH 1 M Inorganic materials 0.000 description 1
- 108010020346 Polyglutamic Acid Proteins 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 238000011481 absorbance measurement Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- JJIPIYZWDNKHCN-UHFFFAOYSA-N azane;propan-2-ol;hydrate Chemical compound N.O.CC(C)O JJIPIYZWDNKHCN-UHFFFAOYSA-N 0.000 description 1
- 239000007853 buffer solution Substances 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 235000011148 calcium chloride Nutrition 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000006482 condensation reaction Methods 0.000 description 1
- DMSZORWOGDLWGN-UHFFFAOYSA-N ctk1a3526 Chemical compound NP(N)(N)=O DMSZORWOGDLWGN-UHFFFAOYSA-N 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- RNOJZAYWQCKGRK-UHFFFAOYSA-N diazene hydrochloride Chemical compound Cl.N=N RNOJZAYWQCKGRK-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003792 electrolyte Substances 0.000 description 1
- 238000002523 gelfiltration Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002605 large molecules Chemical class 0.000 description 1
- 239000004005 microsphere Substances 0.000 description 1
- BOPGDPNILDQYTO-NNYOXOHSSA-N nicotinamide-adenine dinucleotide Chemical class C1=CCC(C(=O)N)=CN1[C@H]1[C@H](O)[C@H](O)[C@@H](COP(O)(=O)OP(O)(=O)OC[C@@H]2[C@H]([C@@H](O)[C@@H](O2)N2C3=NC=NC(N)=C3N=C2)O)O1 BOPGDPNILDQYTO-NNYOXOHSSA-N 0.000 description 1
- 150000005480 nicotinamides Chemical class 0.000 description 1
- 229920002643 polyglutamic acid Polymers 0.000 description 1
- 229920001282 polysaccharide Polymers 0.000 description 1
- 239000005017 polysaccharide Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011240 wet gel Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Saccharide Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Polysaccharides And Polysaccharide Derivatives (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25419/75A IT1039860B (it) | 1975-07-15 | 1975-07-15 | Processo per la preparazione di derivati adeninici funziona lizzati e prodotti cosi ottenuti |
| IT2295876A IT1059785B (it) | 1976-05-04 | 1976-05-04 | Procedimento per la preparazione di derivati adeninici macromoleolarizzati e prodotti cosi ottenuti |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626891A5 true CH626891A5 (en, 2012) | 1981-12-15 |
Family
ID=26328299
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH898276A CH626891A5 (en, 2012) | 1975-07-15 | 1976-07-13 |
Country Status (16)
| Country | Link |
|---|---|
| US (2) | US4091203A (en, 2012) |
| JP (1) | JPS5210292A (en, 2012) |
| AU (1) | AU511507B2 (en, 2012) |
| CA (1) | CA1083567A (en, 2012) |
| CH (1) | CH626891A5 (en, 2012) |
| DD (1) | DD125941A5 (en, 2012) |
| DE (1) | DE2631046A1 (en, 2012) |
| DK (1) | DK317276A (en, 2012) |
| FR (1) | FR2318173A1 (en, 2012) |
| GB (1) | GB1552453A (en, 2012) |
| IL (2) | IL50027A (en, 2012) |
| LU (1) | LU75377A1 (en, 2012) |
| NL (1) | NL7607877A (en, 2012) |
| NO (1) | NO144673C (en, 2012) |
| SE (1) | SE7608064L (en, 2012) |
| YU (2) | YU172576A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5481166U (en, 2012) * | 1977-11-21 | 1979-06-08 | ||
| JPS6121040Y2 (en, 2012) * | 1977-11-25 | 1986-06-24 | ||
| JPS5485574U (en, 2012) * | 1977-11-30 | 1979-06-16 | ||
| JPS5485572U (en, 2012) * | 1977-11-30 | 1979-06-16 | ||
| US4701521A (en) * | 1978-07-17 | 1987-10-20 | The Trustees Of Boston University | Method of effecting cellular uptake of molecules |
| JPS5535495U (en, 2012) * | 1978-08-31 | 1980-03-07 | ||
| AU596068B2 (en) * | 1983-02-22 | 1990-04-26 | Syngene, Inc. | Defined sequence single strand oligonucleotides incorporating reporter groups, process for the chemical synthesis thereof, and nucleosides useful in such synthesis |
| US4948882A (en) * | 1983-02-22 | 1990-08-14 | Syngene, Inc. | Single-stranded labelled oligonucleotides, reactive monomers and methods of synthesis |
| IT1196261B (it) * | 1984-09-20 | 1988-11-16 | Pierrel Spa | Derivati nucleosidici e purinici 8-sostituiti |
| US20030228621A1 (en) * | 2002-05-24 | 2003-12-11 | Yong Qin | Common ligand universal enzyme assay and compositions for use therein |
| US9926340B2 (en) * | 2015-04-08 | 2018-03-27 | The Board Of Regents Of The University Of Texas System | NAD analogs and methods of using said NAD analogs in determining ribosylation of proteins with PARP mutants |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2946781A (en) * | 1957-02-06 | 1960-07-26 | Merck & Co Inc | Process for the preparation of adenosyl homocysteine |
| US3712885A (en) * | 1968-09-10 | 1973-01-23 | G Weimann | Purine-ribofuranoside-3',5'-cyclophosphates and process for their preparation |
| US3989812A (en) * | 1974-08-09 | 1976-11-02 | Smithkline Instruments, Inc. | Folic acid derivatives and use in radio-assay |
-
1976
- 1976-07-09 DE DE19762631046 patent/DE2631046A1/de not_active Withdrawn
- 1976-07-12 FR FR7621344A patent/FR2318173A1/fr active Granted
- 1976-07-12 GB GB28951/76A patent/GB1552453A/en not_active Expired
- 1976-07-12 IL IL50027A patent/IL50027A/xx unknown
- 1976-07-13 DD DD193827A patent/DD125941A5/xx unknown
- 1976-07-13 CA CA256,851A patent/CA1083567A/en not_active Expired
- 1976-07-13 LU LU75377A patent/LU75377A1/xx unknown
- 1976-07-13 YU YU01725/76A patent/YU172576A/xx unknown
- 1976-07-13 CH CH898276A patent/CH626891A5/it not_active IP Right Cessation
- 1976-07-14 DK DK317276A patent/DK317276A/da not_active Application Discontinuation
- 1976-07-14 SE SE7608064A patent/SE7608064L/xx not_active Application Discontinuation
- 1976-07-14 AU AU15853/76A patent/AU511507B2/en not_active Expired
- 1976-07-14 US US05/705,012 patent/US4091203A/en not_active Expired - Lifetime
- 1976-07-15 NL NL7607877A patent/NL7607877A/xx not_active Application Discontinuation
- 1976-07-15 NO NO762485A patent/NO144673C/no unknown
- 1976-07-15 JP JP51083562A patent/JPS5210292A/ja active Pending
-
1978
- 1978-02-22 US US05/880,133 patent/US4336188A/en not_active Expired - Lifetime
-
1979
- 1979-02-14 IL IL56666A patent/IL56666A0/xx unknown
-
1983
- 1983-05-23 YU YU01138/83A patent/YU113883A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO144673B (no) | 1981-07-06 |
| FR2318173B1 (en, 2012) | 1981-11-27 |
| SE7608064L (sv) | 1977-01-16 |
| US4336188A (en) | 1982-06-22 |
| AU1585376A (en) | 1978-01-19 |
| DK317276A (da) | 1977-01-16 |
| GB1552453A (en) | 1979-09-12 |
| YU113883A (en) | 1986-12-31 |
| NL7607877A (nl) | 1977-01-18 |
| DD125941A5 (en, 2012) | 1977-06-01 |
| FR2318173A1 (fr) | 1977-02-11 |
| LU75377A1 (en, 2012) | 1977-02-25 |
| DE2631046A1 (de) | 1977-01-20 |
| IL50027A0 (en) | 1976-09-30 |
| NO144673C (no) | 1981-10-14 |
| JPS5210292A (en) | 1977-01-26 |
| YU172576A (en) | 1983-10-31 |
| NO762485L (en, 2012) | 1977-01-18 |
| IL50027A (en) | 1980-09-16 |
| US4091203A (en) | 1978-05-23 |
| IL56666A0 (en) | 1979-05-31 |
| CA1083567A (en) | 1980-08-12 |
| AU511507B2 (en) | 1980-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20220411860A1 (en) | Design and synthesis of novel disulfide linker based nucleotides as reversible terminators for dna sequencing by synthesis | |
| Krenitsky et al. | Purine nucleoside synthesis: an efficient method employing nucleoside phosphorylases | |
| CH626891A5 (en, 2012) | ||
| Walker et al. | The Covalently‐Bound Flavin of Hepatic Monoamine Oxidase: 2. Identification and Properties of Cysteinyl Riboflavin | |
| Zhang et al. | Designing facial amphiphiles for the stabilization of integral membrane proteins | |
| FI81360C (fi) | Stabila salter mellan s-adenosyl-l-metionin (sam) och polyanjoner. | |
| EP2059510B1 (en) | Sox-based kinase sensor | |
| US5625056A (en) | Derivatives of cyclic guanosine-3',5'-monophosphorothioate | |
| Zappelli et al. | Synthesis of coenzymically active soluble and insoluble macromolecularized NAD+ derivatives | |
| Murphy et al. | Number and location of adenosine triphosphatase sites of myosin | |
| Bailey et al. | Affinity labeling of NADP+-specific isocitrate dehydrogenase by a new fluorescent nucleotide analog, 2-[(4-bromo-2, 3-dioxobutyl) thio]-1, N6-ethenoadenosine 2', 5'-bisphosphate | |
| Kikugawa et al. | Platelet aggregation inhibitors. 6. 2-Thioadenosine derivatives | |
| AU751147B2 (en) | Novel nucleoside or nucleotide fluorescent conjugates, preparation method and uses | |
| Kenney et al. | The covalently bound flavin of Vibrio succinogenes succinate dehydrogenase | |
| Zappelli et al. | New Coenzymically‐Active Soluble and Insoluble Macromolecular NAD+ Derivatives | |
| US4199498A (en) | Macromolecularized adenine derivatives | |
| CS199583B2 (en) | Process for preparing derivatives of adenine | |
| EP0333832B1 (en) | Artificial dna base pair analogues | |
| Zappelli et al. | Carboxylic and Polyethyleneimine‐Bound FAD Derivatives: Synthesis, Coenzymic Properties, Conformational and Enzyme‐Coenzyme Interaction Studies | |
| Ishihama et al. | A Novel Adenosine Triphosphatase Isolated from RNA Polymerase Preparations of Escherichia coli II. Enzymatic Properties and Molecular Structure | |
| Ohtsuka et al. | Studies on Transfer Ribonucleic Acids and Related Compounds. VII. Synthesis and Properties of Cyclic Oligoadenylic Acids | |
| Schäfer | [66] Divalent azido-ATP analog for photoaffinity cross-linking of F1 subunits | |
| CS202046B2 (cs) | Způsob přípravy funkcionalizovaných derivátů adeninu | |
| Reimann et al. | Synthesis and characterization of iodopropyl derivatives of adenosine 3′, 5′-cyclic-monophosphate: Potential affinity labels of cAMP binding sites in enzymes | |
| US5399681A (en) | Method for preparing N6 -substituted NAD, NADP or FAD |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUE | Assignment |
Owner name: ANIC S.P.A. |
|
| PL | Patent ceased | ||
| PL | Patent ceased |