SIMPLIFIED AND COST-EFFECTIVE SYNTHESES OF FULLY PROTECTED PHOSPHORAMIDITE MONOMERS SUITABLE FOR THE ASSEMBLY OF OLIGO(2'-O-ALLYLRIBONUCLEOTIDES)

被引:21
作者
BEIJER, B [1 ]
GROTLI, M [1 ]
DOUGLAS, ME [1 ]
SPROAT, BS [1 ]
机构
[1] EUROPEAN MOLEC BIOL LAB, D-69117 HEIDELBERG, GERMANY
关键词
D O I
10.1080/15257779408010672
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Simplified, high yielding syntheses of suitably protected 2'-O-allylribonucleoside-3'-O-phosphoramidites starting from standard ribonucleosides have been elucidated. Specific 2'-O-allylation is readily achieved using amidine protection of the exocyclic amino groups of adenosine and cytidine and in the case of guanosine the allylation is carried out on an easily prepared intermediate bearing transient protection of the lactam function.
引用
收藏
页码:1905 / 1927
页数:23
相关论文
共 26 条
[1]   ANTISENSE PROBES TARGETED TO AN INTERNAL DOMAIN IN U2 SNRNP SPECIFICALLY INHIBIT THE 2(D STEP OF PRE-MESSENGER-RNA SPLICING [J].
BARABINO, SML ;
SPROAT, BS ;
LAMOND, AI .
NUCLEIC ACIDS RESEARCH, 1992, 20 (17) :4457-4464
[2]   SYNTHESIS AND APPLICATIONS OF OLIGORIBONUCLEOTIDES WITH SELECTED 2'-O-METHYLATION USING THE 2'-O-[1-(2-FLUOROPHENYL)-4-METHOXYPIPERIDIN-4-YL] PROTECTING GROUP [J].
BEIJER, B ;
SULSTON, I ;
SPROAT, BS ;
RIDER, P ;
LAMOND, AI ;
NEUNER, P .
NUCLEIC ACIDS RESEARCH, 1990, 18 (17) :5143-5151
[3]   SYNTHESIS OF THE 3'-TERMINAL HALF OF YEAST ALANINE TRANSFER RIBONUCLEIC-ACID (TRANSFER RNAALA) BY THE PHOSPHOTRIESTER APPROACH IN SOLUTION .1. PREPARATION OF THE NUCLEOSIDE BUILDING-BLOCKS [J].
BROWN, JM ;
CHRISTODOULOU, C ;
JONES, SS ;
MODAK, AS ;
REESE, CB ;
SIBANDA, S ;
UBASAWA, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1989, (10) :1735-1750
[4]   INVIVO DETECTION OF SNRNP-RICH ORGANELLES IN THE NUCLEI OF MAMMALIAN-CELLS [J].
CARMOFONSECA, M ;
PEPPERKOK, R ;
SPROAT, BS ;
ANSORGE, W ;
SWANSON, MS ;
LAMOND, AI .
EMBO JOURNAL, 1991, 10 (07) :1863-1873
[5]   EFFICIENT SYNTHESIS OF 2'-O-ALKYL RIBONUCLEOSIDES USING TRICHLOROACETIMIDATE D-RIBOFURANOSIDES AS RIBOSYL DONORS [J].
CHANTELOUP, L ;
THUONG, NT .
TETRAHEDRON LETTERS, 1994, 35 (06) :877-880
[6]   INTRACELLULAR DISPOSITION AND METABOLISM OF FLUORESCENTLY-LABELED UNMODIFIED AND MODIFIED OLIGONUCLEOTIDES MICROINJECTED INTO MAMMALIAN-CELLS [J].
FISHER, TL ;
TERHORST, T ;
CAO, XD ;
WAGNER, RW .
NUCLEIC ACIDS RESEARCH, 1993, 21 (16) :3857-3865
[7]   REGIOSELECTIVE 2'/3'-O-ALLYLATION OF PYRIMIDINE RIBONUCLEOSIDES USING PHASE-TRANSFER CATALYSIS [J].
GOPALAKRISHNAN, V ;
KUMAR, V ;
GANESH, KN .
NUCLEOSIDES & NUCLEOTIDES, 1992, 11 (06) :1263-1273
[8]   2'-O-ALKYL OLIGORIBONUCLEOTIDES AS ANTISENSE PROBES [J].
IRIBARREN, AM ;
SPROAT, BS ;
NEUNER, P ;
SULSTON, I ;
RYDER, U ;
LAMOND, AI .
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1990, 87 (19) :7747-7751
[9]   REVERSE TRANSCRIPTION USING NUCLEASE RESISTANT PRIMERS [J].
JOHANSSON, HE ;
SPROAT, BS ;
MELEFORS, O .
NUCLEIC ACIDS RESEARCH, 1993, 21 (09) :2275-2276
[10]   A GENERAL-METHOD FOR THE SYNTHESIS OF 2'-O-MODIFIED RIBONUCLEOSIDES [J].
KELLER, TH ;
HANER, R .
HELVETICA CHIMICA ACTA, 1993, 76 (02) :884-892