NEW SYNTHETIC ROUTES TO SYNTHONS SUITABLE FOR 2'-O-ALLYLOLIGORIBONUCLEOTIDE ASSEMBLY

被引：58

作者：

SPROAT, BS ^{[1
]}

IRIBARREN, AM ^{[1
]}

GARCIA, RG ^{[1
]}

BEIJER, B ^{[1
]}

机构：

[1] IST RIC BIOL MOLEC,I-00040 POMEZIA,ITALY

来源：

NUCLEIC ACIDS RESEARCH | 1991年 / 19卷 / 04期

关键词：

D O I：

10.1093/nar/19.4.733

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：

New synthetic routes have been devised for the high yield preparation of protected 2'-O-allylribonucleoside-3'-O-phosphoramidites, exemplified by the ribonucleosides guanosine and 2,6-diaminopurine riboside (2-aminoadenosine). Key features are the use of versatile intermediates and an easy allylation step. The development of a novel synthon based on 2'-O-allyl-2,6-diaminopurine riboside enables short 2'-O-allyloligoribonucleotide probes to be synthesized with adenine replaced by 2-aminoadenine. Thus very stable hybrids with complementary RNA target sequences can be formed due to the formation of the three hydrogen bond 2-amino A.U base pairs.

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页码：733 / 738

页数：6

相关论文

共 24 条

[1] NEW SYNTHETIC TRICKS - [ET3NH][SN(SPH)3] AND BU2SNH2, 2 USEFUL REAGENTS FOR THE REDUCTION OF AZIDES TO AMINES [J].

BARTRA, M ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON LETTERS, 1987, 28 (47) :5941-5944

[2] A FAST PROCEDURE FOR THE REDUCTION OF AZIDES AND NITRO-COMPOUNDS BASED ON THE REDUCING ABILITY OF SN(SR)3-SPECIES [J].

BARTRA, M ;

ROMEA, P ;

URPI, F ;

VILARRASA, J .

TETRAHEDRON, 1990, 46 (02) :587-594

[3] INTERACTION OF ACTINOMYCIN WITH DNA - REQUIREMENT FOR 2-AMINO GROUP OF PURINES [J].

CERAMI, A ;

REICH, E ;

WARD, DC ;

GOLDBERG, IH .

PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA, 1967, 57 (04) :1036-&

[4] THE USE OF LABILE BASE PROTECTING GROUPS IN OLIGORIBONUCLEOTIDE SYNTHESIS [J].

CHAIX, C ;

MOLKO, D ;

TEOULE, R .

TETRAHEDRON LETTERS, 1989, 30 (01) :71-74

[5]

CHOLLET A, 1986, CHEM SCRIPTA, V26, P37

[6]

FURUKAWA Y, 1965, CHEM PHARM BULL, V13, P1273

[7] THE INFLUENCE OF THE PURINE 2-AMINO GROUP ON DNA CONFORMATION AND STABILITY .2. SYNTHESIS AND PHYSICAL CHARACTERIZATION OF D[CGT(2-NH2)ACG], D[CGU(2-NH2)ACG], AND D[CGT(2-NH2)AT(2-NH2)ACG] [J].

GAFFNEY, BL ;

MARKY, LA ;

JONES, RA .

TETRAHEDRON, 1984, 40 (01) :3-13

[8] 2NH2A.T HELICES IN THE RIBOPOLYNUCLEOTIDE AND DEOXYPOLYNUCLEOTIDE SERIES - STRUCTURAL AND ENERGETIC CONSEQUENCES OF 2NH2A SUBSTITUTION [J].

HOWARD, FB ;

MILES, HT .

BIOCHEMISTRY, 1984, 23 (26) :6723-6732

[9] 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

[10] THE PROTECTION OF URACIL AND GUANINE RESIDUES IN OLIGONUCLEOTIDE SYNTHESIS [J].

JONES, SS ;

REESE, CB ;

SIBANDA, S ;

UBASAWA, A .

TETRAHEDRON LETTERS, 1981, 22 (47) :4755-4758