Literature DB >> 3774550

A simple and efficient procedure for the synthesis of 5'-aminoalkyl oligodeoxynucleotides.

L Wachter, J A Jablonski, K L Ramachandran.   

Abstract

Synthetic deoxyoligonucleotides have been 5'-aminoalkylated at the end of step-wise synthesis on the polymer support. This was achieved through the activation of the 5'-hydroxyl group as its 5'-imidazolyl derivative using carbonyldiimidazole, which was subsequently displaced with hexamethylene diamine to yield the title compound. The alkyl carbamate linkage thus generated withstands the deprotection conditions used in oligonucleotide synthesis. Purification by gel electrophoresis and further derivatization at the 5'-amino group with N-hydroxysuccinimidobiotin is described.

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Year:  1986        PMID: 3774550      PMCID: PMC311829          DOI: 10.1093/nar/14.20.7985

Source DB:  PubMed          Journal:  Nucleic Acids Res        ISSN: 0305-1048            Impact factor:   16.971


  11 in total

1.  Steroidal imidazole-1-carboxylic acid esters.

Authors:  K E Fahrenholtz; A Boris; T W Kennedy; R W Kierstead
Journal:  J Med Chem       Date:  1974-03       Impact factor: 7.446

2.  Application of 1,1'-carbonyldiimidazole-activated agarose for the purification of proteins. II. The use of an activated matrix devoid of additional charged groups for the purification of thyroid proteins.

Authors:  M T Hearn; G S Bethell; J S Ayers; W S Hancock
Journal:  J Chromatogr       Date:  1979-12-20

3.  A new linkage for solid phase synthesis of oligodeoxyribonucleotides.

Authors:  B S Sproat; D M Brown
Journal:  Nucleic Acids Res       Date:  1985-04-25       Impact factor: 16.971

4.  Biotin-labeled synthetic oligodeoxyribonucleotides: chemical synthesis and uses as hybridization probes.

Authors:  A Chollet; E H Kawashima
Journal:  Nucleic Acids Res       Date:  1985-03-11       Impact factor: 16.971

5.  Detection of specific DNA sequences with short biotin-labeled probes.

Authors:  B C Chu; L E Orgel
Journal:  DNA       Date:  1985-08

6.  Chemical synthesis of oligonucleotides containing a free sulphydryl group and subsequent attachment of thiol specific probes.

Authors:  B A Connolly; P Rider
Journal:  Nucleic Acids Res       Date:  1985-06-25       Impact factor: 16.971

7.  The synthesis of oligonucleotides containing an aliphatic amino group at the 5' terminus: synthesis of fluorescent DNA primers for use in DNA sequence analysis.

Authors:  L M Smith; S Fung; M W Hunkapiller; T J Hunkapiller; L E Hood
Journal:  Nucleic Acids Res       Date:  1985-04-11       Impact factor: 16.971

8.  Rapid and sensitive colorimetric method for visualizing biotin-labeled DNA probes hybridized to DNA or RNA immobilized on nitrocellulose: Bio-blots.

Authors:  J J Leary; D J Brigati; D C Ward
Journal:  Proc Natl Acad Sci U S A       Date:  1983-07       Impact factor: 11.205

9.  A novel method of activation of cross-linked agaroses with 1,1'-carbonyldiimidazole which gives a matrix for affinity chromatography devoid of additional charged groups.

Authors:  G S Bethell; J S Ayers; W S Hancock; M T Hearn
Journal:  J Biol Chem       Date:  1979-04-25       Impact factor: 5.157

10.  Application of 1,1'-carbonyldiimidazole-activated matrices for the purification of proteins. III. The use of 1,1'-carbonyldiimidazole-activated agaroses in the biospecific affinity chromatographic isolation of serum antibodies.

Authors:  M T Hearn; E L Harris; G S Bethell; W S Hancock; J A Ayers
Journal:  J Chromatogr       Date:  1981-11-20
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  18 in total

1.  Intracellular distribution of microinjected antisense oligonucleotides.

Authors:  J P Leonetti; N Mechti; G Degols; C Gagnor; B Lebleu
Journal:  Proc Natl Acad Sci U S A       Date:  1991-04-01       Impact factor: 11.205

2.  Chemiluminescent detection of DNA: application for DNA sequencing and hybridization.

Authors:  S Beck; T O'Keeffe; J M Coull; H Köster
Journal:  Nucleic Acids Res       Date:  1989-07-11       Impact factor: 16.971

3.  Cleavage of double-stranded DNA by 'metalloporphyrin-linker-oligonucleotide' molecules: influence of the linker.

Authors:  P Bigey; G Pratviel; B Meunier
Journal:  Nucleic Acids Res       Date:  1995-10-11       Impact factor: 16.971

4.  The synthesis of protected 5'-amino-2',5'-dideoxyribonucleoside-3'-O-phosphoramidites; applications of 5'-amino-oligodeoxyribonucleotides.

Authors:  B S Sproat; B Beijer; P Rider
Journal:  Nucleic Acids Res       Date:  1987-08-11       Impact factor: 16.971

5.  Synthesis and antibody-mediated detection of oligonucleotides containing multiple 2,4-dinitrophenyl reporter groups.

Authors:  J Grzybowski; D W Will; R E Randall; C A Smith; T Brown
Journal:  Nucleic Acids Res       Date:  1993-04-25       Impact factor: 16.971

6.  Oligonucleotides, part 5+: synthesis and fluorescence studies of DNA oligomers d(AT)5 containing adenines covalently linked at C-8 with dansyl fluorophore.

Authors:  D Singh; V Kumar; K N Ganesh
Journal:  Nucleic Acids Res       Date:  1990-06-11       Impact factor: 16.971

7.  Synthesis and hybridization of a series of biotinylated oligonucleotides.

Authors:  A F Cook; E Vuocolo; C L Brakel
Journal:  Nucleic Acids Res       Date:  1988-05-11       Impact factor: 16.971

8.  Drug targeting: synthesis and endocytosis of oligonucleotide-neoglycoprotein conjugates.

Authors:  E Bonfils; C Depierreux; P Midoux; N T Thuong; M Monsigny; A C Roche
Journal:  Nucleic Acids Res       Date:  1992-09-11       Impact factor: 16.971

9.  Antisense phosphorothioate oligonucleotides: selective killing of the intracellular parasite Leishmania amazonensis.

Authors:  C Ramazeilles; R K Mishra; S Moreau; E Pascolo; J J Toulmé
Journal:  Proc Natl Acad Sci U S A       Date:  1994-08-16       Impact factor: 11.205

10.  Linkage structures strongly influence the binding cooperativity of DNA intercalators conjugated to triplex forming oligonucleotides.

Authors:  F M Orson; B M Kinsey; W M McShan
Journal:  Nucleic Acids Res       Date:  1994-02-11       Impact factor: 16.971

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