Literature DB >> 2717397

Solid-phase synthesis of oligoribonucleotides using 9-fluorenylmethoxycarbonyl (Fmoc) for 5'-hydroxyl protection.

C Lehmann1, Y Z Xu, C Christodoulou, Z K Tan, M J Gait.   

Abstract

Efficient solid-phase synthesis of a series of oligoribonucleotides of up to 20 residues is described that utilises the 9-fluorenylmethoxycarbonyl group (Fmoc) for 5'-protection and 4-methoxytetrahydropyran-4-yl (Mthp) for 2'-protection of ribonucleotide monomers and a phosphoramidite coupling procedure. The Fmoc group is removed after each coupling step by treatment with 0.1M DBU in acetonitrile. Oligoribonucleotides are isolated in 2'-protected form in good yield and shown to be readily and efficiently deprotected by mild acidic treatment.

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Year:  1989        PMID: 2717397      PMCID: PMC317630          DOI: 10.1093/nar/17.7.2379

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


  9 in total

1.  The synthesis of oligoribonucleotides. Part XI. Preparation of ribonucleoside 2'-acetal 3'-esters by selective deacylation.

Authors:  C B Reese; J C Stewart; J H van Boom; H P de Leeuw; J Nagel; J F de Rooy
Journal:  J Chem Soc Perkin 1       Date:  1975

2.  Synthesis of RNA oligomer using 9-fluorenylmethoxycarbonyl (Fmoc) group for 5'-hydroxyl protection.

Authors:  T Fukuda; T Hamana; R Marumoto
Journal:  Nucleic Acids Symp Ser       Date:  1988

3.  Solid phase synthesis of oligoribonucleotides using the o-nitrobenzyl group for 2'-hydroxyl protection and H-phosphonate chemistry.

Authors:  T Tanaka; S Tamatsukuri; M Ikehara
Journal:  Nucleic Acids Res       Date:  1987-09-25       Impact factor: 16.971

4.  Solid phase synthesis of oligoribonucleotides using o-nitrobenzyl protection of 2'-hydroxyl via a phosphite triester approach.

Authors:  T Tanaka; S Tamatsukuri; M Ikehara
Journal:  Nucleic Acids Res       Date:  1986-08-11       Impact factor: 16.971

5.  5'-Levulinyl and 2'-tetrahydrofuranyl protection for the synthesis of oligoribonucleotides by the phosphoramidite approach.

Authors:  S Iwai; E Ohtsuka
Journal:  Nucleic Acids Res       Date:  1988-10-25       Impact factor: 16.971

6.  Studies on the t-butyldimethylsilyl group as 2'-O-protection in oligoribonucleotide synthesis via the H-phosphonate approach.

Authors:  J Stawinski; R Strömberg; M Thelin; E Westman
Journal:  Nucleic Acids Res       Date:  1988-10-11       Impact factor: 16.971

7.  Action of acid on oligoribonucleotide phosphotriester intermediates. Effect of released vicinal hydroxy functions.

Authors:  C B Reese; P A Skone
Journal:  Nucleic Acids Res       Date:  1985-07-25       Impact factor: 16.971

8.  Total chemical synthesis of a 77-nucleotide-long RNA sequence having methionine-acceptance activity.

Authors:  K K Ogilvie; N Usman; K Nicoghosian; R J Cedergren
Journal:  Proc Natl Acad Sci U S A       Date:  1988-08       Impact factor: 11.205

9.  Polymer support oligonucleotide synthesis XVIII: use of beta-cyanoethyl-N,N-dialkylamino-/N-morpholino phosphoramidite of deoxynucleosides for the synthesis of DNA fragments simplifying deprotection and isolation of the final product.

Authors:  N D Sinha; J Biernat; J McManus; H Köster
Journal:  Nucleic Acids Res       Date:  1984-06-11       Impact factor: 16.971

  9 in total
  12 in total

1.  Chemical synthesis of biologically active oligoribonucleotides using beta-cyanoethyl protected ribonucleoside phosphoramidites.

Authors:  S A Scaringe; C Francklyn; N Usman
Journal:  Nucleic Acids Res       Date:  1990-09-25       Impact factor: 16.971

2.  Chemical synthesis of the 24 RNA fragments corresponding to hop stunt viroid.

Authors:  H Tanimura; M Maeda; T Fukazawa; M Sekine; T Hata
Journal:  Nucleic Acids Res       Date:  1989-10-25       Impact factor: 16.971

3.  Synthesis and radioiodination of a stannyl oligodeoxyribonucleotide.

Authors:  H Dougan; J B Hobbs; J I Weitz; D M Lyster
Journal:  Nucleic Acids Res       Date:  1997-07-15       Impact factor: 16.971

4.  Novel route to oligo(deoxyribonucleoside phosphorothioates). Stereocontrolled synthesis of P-chiral oligo(deoxyribonucleoside phosphorothioates).

Authors:  W J Stec; A Grajkowski; M Koziolkiewicz; B Uznanski
Journal:  Nucleic Acids Res       Date:  1991-11-11       Impact factor: 16.971

5.  Generation and screening of an oligonucleotide-encoded synthetic peptide library.

Authors:  M C Needels; D G Jones; E H Tate; G L Heinkel; L M Kochersperger; W J Dower; R W Barrett; M A Gallop
Journal:  Proc Natl Acad Sci U S A       Date:  1993-11-15       Impact factor: 11.205

6.  Orthogonal combinatorial mutagenesis: a codon-level combinatorial mutagenesis method useful for low multiplicity and amino acid-scanning protocols.

Authors:  P Gaytán; J Yáñez; F Sánchez; X Soberón
Journal:  Nucleic Acids Res       Date:  2001-02-01       Impact factor: 16.971

7.  Synthesis and applications of oligoribonucleotides with selected 2'-O-methylation using the 2'-O-[1-(2-fluorophenyl)-4-methoxypiperidin-4-yl] protecting group.

Authors:  B Beijer; I Sulston; B S Sproat; P Rider; A I Lamond; P Neuner
Journal:  Nucleic Acids Res       Date:  1990-09-11       Impact factor: 16.971

8.  Synthetic approach to stop-codon scanning mutagenesis.

Authors:  Lihua Nie; Jason J Lavinder; Mohosin Sarkar; Kimberly Stephany; Thomas J Magliery
Journal:  J Am Chem Soc       Date:  2011-03-31       Impact factor: 15.419

9.  Dimerization in highly concentrated solutions of phosphoimidazolide activated mononucleotides.

Authors:  A Kanavarioti
Journal:  Orig Life Evol Biosph       Date:  1997-08       Impact factor: 1.950

10.  Novel ceftazidime-resistance beta-lactamases generated by a codon-based mutagenesis method and selection.

Authors:  Paul Gaytán; Joel Osuna; Xavier Soberón
Journal:  Nucleic Acids Res       Date:  2002-08-15       Impact factor: 16.971

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