DEP0032285DA - Process for the preparation of nucleosides from nucleic acid - Google Patents
Process for the preparation of nucleosides from nucleic acidInfo
- Publication number
- DEP0032285DA DEP0032285DA DEP0032285DA DE P0032285D A DEP0032285D A DE P0032285DA DE P0032285D A DEP0032285D A DE P0032285DA
- Authority
- DE
- Germany
- Prior art keywords
- nucleosides
- preparation
- nucleic acid
- carbonates
- known manner
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title claims 2
- 239000002777 nucleoside Substances 0.000 title claims 2
- 125000003835 nucleoside group Chemical group 0.000 title claims 2
- 150000007523 nucleic acids Chemical class 0.000 title 1
- 102000039446 nucleic acids Human genes 0.000 title 1
- 108020004707 nucleic acids Proteins 0.000 title 1
- 229910019142 PO4 Inorganic materials 0.000 claims description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims description 2
- 238000003776 cleavage reaction Methods 0.000 claims description 2
- 235000021317 phosphate Nutrition 0.000 claims description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 claims description 2
- 230000007017 scission Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 229910052788 barium Inorganic materials 0.000 claims 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229910052749 magnesium Inorganic materials 0.000 claims 1
- 239000011777 magnesium Substances 0.000 claims 1
- NYHBQMYGNKIUIF-UUOKFMHZSA-N Guanosine Chemical compound C1=NC=2C(=O)NC(N)=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O NYHBQMYGNKIUIF-UUOKFMHZSA-N 0.000 description 5
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- MIKUYHXYGGJMLM-GIMIYPNGSA-N Crotonoside Natural products C1=NC2=C(N)NC(=O)N=C2N1[C@H]1O[C@@H](CO)[C@H](O)[C@@H]1O MIKUYHXYGGJMLM-GIMIYPNGSA-N 0.000 description 2
- NYHBQMYGNKIUIF-UHFFFAOYSA-N D-guanosine Natural products C1=2NC(N)=NC(=O)C=2N=CN1C1OC(CO)C(O)C1O NYHBQMYGNKIUIF-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- 229940029575 guanosine Drugs 0.000 description 2
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 1
- 229960005305 adenosine Drugs 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000015110 jellies Nutrition 0.000 description 1
- 239000008274 jelly Substances 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229940088417 precipitated calcium carbonate Drugs 0.000 description 1
- 239000002718 pyrimidine nucleoside Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
Description
ZS!,L8!P0fFfABRBf !„COFiOf Mamlieim~Vialdaof, 16,6*5©ZS!, L8! P0fFfABRBf! "COF i Of Mamlie im ~ Vialdaof, 16.6 * 5 ©
Keiuihe Ia-Waldhof 16/66/t Keiuihe Ia-Waldhof 1 6/66 / t
P 32285 Πθ/12 ρ D v,22.1,49 P 32285 Πθ / 12 ρ D v , 22 .1.49
Terfabxea ssa? iewiastuag ¥©b Xfncleoelden mm IaeleinsciBij©Terfabxea ssa? iewiastuag ¥ © b Xfncleoelden mm IaeleinsciBi j ©
Biö Gewinnung ¥©a Hoeleoelden durch hyclrolyt loche Spalttaag von XTtiDlelneaare feenn nseh bekaantea Ierfalirea durch 3*4 ettiadige Behaiidluiiig mit MBmntgk bei 175 ~ 18o° ei?f©Xg@a* 1@» erhalt Iiiertiei ©is Ssaiseli tes Parin- and Pyrimidinnucleoside« Biö recovery ¥ © a Hoeleoelden by hyclrolyt Punch Spalttaag of XTtiDlelneaare feenn nseh bekaantea Ierfalirea by 3 * 4 ettiadige Behaiidluiiig with MBmntgk at 175 ~ 18o ° ei? F © Xg @ a @ * 1 "sustaining Iiiertiei © is Ssaiseli te s Parin- and Pyrimidine nucleosides "
Heohteilig bei dleeera FerfsJircn let, dad mcm. eise schlechte Anebeute erhält end alt BruelcgefSUiea arbeite» sal* Arbeitet sea unter milderen. Bedlngongeaf n»!* bei 115°» eo nia?i die Hnelela«' ©iiw© traf ble sä fiea HoaonucleotiAea mbgebeat* Heohteilig at dleeera FerfsJircn let, dad mcm. ice poor ane prey receives end old BruelcgefSUiea work »sal * works sea under milder. Bedlngongea f n »! * At 115 °» eo nia? I die Hnelela «' © iiw © traf ble sä fiea HoaonucleotiAea mbgebeat *
Msn hat dota? (»®»t©ch© Patentschrift B93 416) die Verffeadung flüchtiger organischer Baeeay wie PyxsIfiia und Cklxiollnt vorgescfelagea» wobei die Spaltung der Kaolelnefture la etwa 96 Standen beendet Iste Die Austseftte aa Gaaaoela tmd Aienesia let «eeeatlioli teener al© eel Venvenduag von Ammealafc· Msn did dota? ( "®" t © ch © Patent B93 416) the Verffeadung volatile organic Baeea y as Pyx s Ifiia and Cklxiolln t vorgescfelagea "the split in the Kaolelnefture la has terminated about 96 Standen e The Austseftte aa Gaaaoela tmd Aienesia let" eeeatlioli teener al © eel Venvenduag by Ammealafc
la wurde an» überraschenderweiee gefeBÄ@aÄ d&S die %fe&ly@© der Hoelelae^ure a&eh ohae ferwanioag der bisher benutßtea eaosw gtssieeltes a»4 ergaaleehea Baeea gelingt» mim aus nm dafür eergt, 4aB dt© bei 4er Spaltimg frelwerdeade £hoephore&uxe a» dem tesfetio»©g«aiseIi entfernt wird. Sie© keaa ®aa da&ureh erreichen, äeS mm aa den HuelelaeBure-ttaeeorgeaieolt, gegebeaeaf&lle uater Iasats orgej&eeher W®w&g,s&ttt€l$ w©l©he die Huelelae&ure so. löse» v@naigeaf wi© β·Β· Alkohole, Polyalkohole» Kther» Bekmr«» 18 el lohe Metellfcy&xwgde oder Ietallsilse aaeetat, tie sit der Phosphorsäure unlösliche Phosphate bilden. la was to "überraschenderweiee gefeBÄ @ a Ä d & S% fe & ly @ © The Hoelelae ^ ure a & eh ohae ferwanioag the Baeea succeed been benutßtea eaosw gtssieeltes a" 4 ergaaleehea "mim from nm for eergt, 4aB dt © at 4p Spaltimg frelwerdeade £ hoephore & uxe a » the tesfetio» © g «aiseIi is removed. You reach © keaa ®aa da & ureh, äeS mm aa the HuelelaeBure-ttaeeorgeaieolt, gebeaf & lle uater Iasats orgej & eeher W®w & g, s & ttt € l $ w © l © he die Huelelae & ure so. dissolve »v @ naigea f wi © β · Β · alcohols, polyalcohols» Kther » Bekmr« » 18 el lohe Metellfcy & xwgde or Ietallsilse aaeetat, after the phosphoric acid form insoluble phosphates.
ISegaesiaasi Galeiwis aod B&riwa®* DaxohfQliriing der Hydrolyee ©rhitBt man die Wucle insnureauf Schiebung Μ© jsur vollständigen Abspaltung der Phosphorsäure« Se ergibt sich der Vorteil, daß die Bedingungen der Spaltung besondere schonend sind and die Benutzung kostspieliger Chemikalien ©fitfällt*ISegaesiaas i Galeiwis aod B & riwa® * DaxohfQliriing the hydrolysis © rhitBe the growth is only postponed Μ © jsur complete elimination of the phosphoric acid «This results in the advantage that the conditions of the cleavage are particularly gentle and the use of expensive chemicals is necessary *
Ioo g Bohnaoleinsivure in 1ooo ecm Wasser» die am durch Zugabe ▼on Natronlauge auf pg? neutralisiert hat, werden mit 4o g gefälltem Calciumcarbonat versetzt und sieben Tage am ßüekflußkfihler gekocht, Ioo g of bean oleinic acid in 1ooo ecm of water »which by adding ▼ on caustic soda to pg? has neutralized, are mixed with 40 g of precipitated calcium carbonate and boiled for seven days on the flow cooler,
Mmh Bntfemen dee ungelösten Anteiles kristallisiert das Guanosin aus« das abgetrennt werden kann. Fällt das Guano sin als Gallerte an, so kann eo nach den bekannten Vorfahren über die Bleiverbindung gereinigt werden. Aus dem Plltrat werden Adenosin und die Pyrimidinnuoleoside in bekannter Welse erhalten. Ausbeute to g Guanosin und 8 g Adenoein, Mmh removal of the undissolved portion crystallizes out the guanosine, which can be separated off. If the guano sin accumulates as jelly, it can be cleaned using the lead compound according to the known ancestors. Adenosine and the pyrimidine nuoleosides are obtained from the Plltrat in a known manner. Yield to g guanosine and 8 g adenoein,
Claims (1)
Family
ID=
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