USRE34069E - Process for the preparation of oligonucleotides - Google Patents
Process for the preparation of oligonucleotides Download PDFInfo
- Publication number
- USRE34069E USRE34069E US07/481,572 US48157290A USRE34069E US RE34069 E USRE34069 E US RE34069E US 48157290 A US48157290 A US 48157290A US RE34069 E USRE34069 E US RE34069E
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- United States
- Prior art keywords
- nucleoside
- protected
- carrier
- group
- groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H21/00—Compounds containing two or more mononucleotide units having separate phosphate or polyphosphate groups linked by saccharide radicals of nucleoside groups, e.g. nucleic acids
Abstract
Description
TABLE 1 __________________________________________________________________________ Physical data of β-cyanoethyl phosphoramidochloridites 3a 3b 3c Compound L = N,N-dimethylamino L = N,N-diisopropylamino L = N-morpholino __________________________________________________________________________ Boiling point 90-92°/0.6 nm 103-5°/0.06 nm -- Chemical shift.sup.(2) 175.97 ppm 179.82 ppm 168.22 ppm in .sup.31 P NMR in CH.sub.3 CN Chemical shift in 4.01, 4.17(2t, POCH.sub.2, 2H) 4.02, 4.2(2t, POCH.sub.2, 2H) 3.96, 4.1(2t, POCH.sub.2, 2H) .sup.1 H NMR in ppm 2.71(t, CH.sub.2CN, 2H) 3.8(m, N(CH).sub.2, 2H) 3.67(t, O(CH.sub.2).sub.2, 4H) 2.7(d, N(CH.sub.3).sub.2, 6H) 2.77(t, CH.sub.2 CH, 2H) 3.17(m, PN(CH.sub.2).sub.2, 4H) 1.29(d, NCH(CH.sub.3).sub.2, 12H) 2.74(t, CH.sub.2CN.sub.2, 2H) Mass spectrum ##STR11## ##STR12## (Cl), 136(C.sub.2 H.sub.6 N), 110 (Cl), 166(C.sub.3 H.sub.4 NO), (Cl), 152(C.sub.3 H.sub.4 NO), (C.sub.3 H.sub.4 NO) 136(C.sub.6 H.sub.14 N) 136(C.sub.4 H.sub.8 O) __________________________________________________________________________ .sup.(1) The crude product after removal of amine hydrochloride and compounds volatile under high vacuum at room temperature has a purity of 93-95% according to the .sup.31 P NMR spectrum .sup.(2) The chemical shifts are determined in acetoned.sub.6 with 80% strength H.sub.3 PO.sub.4 as the external standard.
Claims (19)
--NR.sub.2.sup.4 ( VIII)
--NR.sub.2.sup.4 (VIII)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US07/481,572 USRE34069E (en) | 1983-08-18 | 1990-02-16 | Process for the preparation of oligonucleotides |
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19833329892 DE3329892A1 (en) | 1983-08-18 | 1983-08-18 | METHOD FOR PRODUCING OLIGONUCLEOTIDES |
US06/752,178 US4725677A (en) | 1983-08-18 | 1984-08-10 | Process for the preparation of oligonucleotides |
US07/481,572 USRE34069E (en) | 1983-08-18 | 1990-02-16 | Process for the preparation of oligonucleotides |
Related Parent Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US06752178 Reissue | 1984-08-10 |
Publications (1)
Publication Number | Publication Date |
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USRE34069E true USRE34069E (en) | 1992-09-15 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US07/481,572 Expired - Lifetime USRE34069E (en) | 1983-08-18 | 1990-02-16 | Process for the preparation of oligonucleotides |
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US (1) | USRE34069E (en) |
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