Literature DB >> 1329028

Incorporation of hexose nucleoside analogues into oligonucleotides: synthesis, base-pairing properties and enzymatic stability.

K Augustyns1, F Vandendriessche, A Van Aerschot, R Busson, C Urbanke, P Herdewijn.   

Abstract

Oligonucleotides containing 1-(2,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (2) and 1-(3,4-dideoxy-beta-D-erythro-hexopyranosyl)thymine (3) were synthesized on a solid support using the phosphoramidite approach. The properties of these oligonucleotides were compared with the earlier reported characteristics of oligonucleotides containing 1-(2,3-dideoxy-beta-D-erythro-hexopyranosyl) thymine (1). The order in enzymatic stability of end-substituted oligonucleotides is 3 greater than 1 much greater than 2. The hybridization properties of the modified oligonucleotides are in reverse order: 2 much greater than 1 greater than 3.

Entities:  

Mesh：

Substances：

Year:  1992        PMID： 1329028      PMCID： PMC334221          DOI： 10.1093/nar/20.18.4711

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


  10 in total

1.  Sugar modified oligonucleotides. I. Carbo-oligodeoxynucleotides as potential antisense agents.

Authors:  M Perbost; M Lucas; C Chavis; A Pompon; H Baumgartner; B Rayner; H Griengl; J L Imbach
Journal:  Biochem Biophys Res Commun       Date:  1989-12-15       Impact factor: 3.575

2.  Predicting DNA duplex stability from the base sequence.

Authors:  K J Breslauer; R Frank; H Blöcker; L A Marky
Journal:  Proc Natl Acad Sci U S A       Date:  1986-06       Impact factor: 11.205

3.  Derivatization of controlled pore glass beads for solid phase oligonucleotide synthesis.

Authors:  R T Pon; N Usman; K K Ogilvie
Journal:  Biotechniques       Date:  1988-09       Impact factor: 1.993

4.  Base-base mismatches. Thermodynamics of double helix formation for dCA3XA3G + dCT3YT3G (X, Y = A,C,G,T).

Authors:  F Aboul-ela; D Koh; I Tinoco; F H Martin
Journal:  Nucleic Acids Res       Date:  1985-07-11       Impact factor: 16.971

5.  Biochemical properties of oligo [(+)-carbocyclic-thymidylates] and their complexes.

Authors:  J Sági; A Szemzõ; J Szécsi; L Otvös
Journal:  Nucleic Acids Res       Date:  1990-04-25       Impact factor: 16.971

6.  2'-O-alkyl oligoribonucleotides as antisense probes.

Authors:  A M Iribarren; B S Sproat; P Neuner; I Sulston; U Ryder; A I Lamond
Journal:  Proc Natl Acad Sci U S A       Date:  1990-10       Impact factor: 11.205

7.  Synthesis and base-pairing properties of the nuclease-resistant alpha-anomeric dodecaribonucleotide alpha-[r(UCUUAACCCACA)].

Authors:  F Debart; B Rayner; G Degols; J L Imbach
Journal:  Nucleic Acids Res       Date:  1992-03-25       Impact factor: 16.971

8.  Uncharged stereoregular nucleic acid analogs: 2. Morpholino nucleoside oligomers with carbamate internucleoside linkages.

Authors:  E P Stirchak; J E Summerton; D D Weller
Journal:  Nucleic Acids Res       Date:  1989-08-11       Impact factor: 16.971

9.  New synthetic routes to protected purine 2'-O-methylriboside-3'-O-phosphoramidites using a novel alkylation procedure.

Authors:  B S Sproat; B Beijer; A Iribarren
Journal:  Nucleic Acids Res       Date:  1990-01-11       Impact factor: 16.971

10.  Sequence-selective recognition of DNA by strand displacement with a thymine-substituted polyamide.

Authors:  P E Nielsen; M Egholm; R H Berg; O Buchardt
Journal:  Science       Date:  1991-12-06       Impact factor: 47.728
  10 in total
  10 in total

1.  Hybrid characteristics of oligonucleotides consisting of isonucleoside 2',5'-anhydro-3'-deoxy-3'-(thymin-1-yl)-D-mannitol with different linkage modes.

Authors:  Z Lei; L Zhang; L R Zhang; J Chen; J M Min; L H Zhang
Journal:  Nucleic Acids Res       Date:  2001-04-01       Impact factor: 16.971

2.  Preorganization of DNA: Design Principles for Improving Nucleic Acid Recognition by Synthetic Oligonucleotides.

Authors:  Eric T. Kool
Journal:  Chem Rev       Date:  1997-08-05       Impact factor: 60.622

3.  DNA duplexes with reactive dialdehyde groups as novel reagents for cross-linking to restriction- modification enzymes.

Authors:  M G Brevnov; O M Gritsenko; S N Mikhailov; E V Efimtseva; B S Ermolinsky; A Van Aerschot; P Herdewijn; A V Repyk; E S Gromova
Journal:  Nucleic Acids Res       Date:  1997-08-15       Impact factor: 16.971

4.  Synthesis and properties of oligodeoxynucleotides containing the analogue 2'-deoxy-4'-thiothymidine.

Authors:  E L Hancox; B A Connolly; R T Walker
Journal:  Nucleic Acids Res       Date:  1993-07-25       Impact factor: 16.971

5.  Incorporation of 2'-amido-nucleosides in oligodeoxynucleotides and oligoribonucleotides as a model for 2'-linked conjugates.

Authors:  C Hendrix; B Devreese; J Rozenski; A van Aerschot; A De Bruyn; J Van Beeumen; P Herdewijn
Journal:  Nucleic Acids Res       Date:  1995-01-11       Impact factor: 16.971

6.  Hybridization specificity, enzymatic activity and biological (Ha-ras) activity of oligonucleotides containing 2,4-dideoxy-beta-D-erythro-hexopyranosyl nucleosides.

Authors:  K Augustyns; G Godard; C Hendrix; A Van Aerschot; J Rozenski; T Saison-Behmoaras; P Herdewijn
Journal:  Nucleic Acids Res       Date:  1993-10-11       Impact factor: 16.971

7.  An expression based clonality assay at the human androgen receptor locus (HUMARA) on chromosome X.

Authors:  L Busque; J Zhu; D DeHart; B Griffith; C Willman; R Carroll; P M Black; D G Gilliland
Journal:  Nucleic Acids Res       Date:  1994-02-25       Impact factor: 16.971

8.  Incorporation of (R)- and (S)-3',4'-seco-thymidine into oligodeoxynucleotides: hybridization properties and enzymatic stability.

Authors:  P Nielsen; F Kirpekar; J Wengel
Journal:  Nucleic Acids Res       Date:  1994-03-11       Impact factor: 16.971

9.  Ru-catalyzed sequence for the synthesis of cyclic amido-ethers.

Authors:  Barry M Trost; Ehesan U Sharif; James J Cregg
Journal:  Chem Sci       Date:  2016-09-12       Impact factor: 9.825

10.  Dideoxy fluoro-ketopyranosyl nucleosides as potent antiviral agents: synthesis and biological evaluation of 2,3- and 3,4-dideoxy-3-fluoro-4- and -2-keto-beta-d-glucopyranosyl derivatives of N(4)-benzoyl cytosine.

Authors:  Stella Manta; Evangelia Tsoukala; Niki Tzioumaki; Ales Goropevsek; Ravi Teja Pamulapati; Avrelija Cencic; Jan Balzarini; Dimitri Komiotis
Journal:  Eur J Med Chem       Date:  2009-01-29       Impact factor: 6.514
  10 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.