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Literature DB >> 20108910

N(2)-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA.

Hayden Peacock¹, Olena Maydanovych, Peter A Beal.

Abstract

Nucleoside analogs that project substituents into the minor groove when incorporated into duplex RNA perturb the binding of proteins and can affect base pairing specificity. The synthesis of 2-aminopurine ribonucleoside analogs and their phosphoramidites, their incorporation into duplex RNA, their postsynthetic modification via Cu-catalyzed azide-alkyne cycloaddition (CuAAC), and their effect on duplex stability and base pairing specificity are described.

Entities: Chemical Gene Species

Mesh：

Substances：

Year: 2010 PMID： 20108910 PMCID： PMC2830388 DOI： 10.1021/ol100019r

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

24 in total

1. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.

Authors: Vsevolod V Rostovtsev; Luke G Green; Valery V Fokin; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2002-07-15 Impact factor: 15.336

2. Structural basis for recognition of the AGNN tetraloop RNA fold by the double-stranded RNA-binding domain of Rnt1p RNase III.

Authors: Haihong Wu; Anthony Henras; Guillaume Chanfreau; Juli Feigon
Journal: Proc Natl Acad Sci U S A Date: 2004-05-18 Impact factor: 11.205

3. The binding selectivity of ADAR2's dsRBMs contributes to RNA-editing selectivity.

Authors: Olen M Stephens; Brittany L Haudenschild; Peter A Beal
Journal: Chem Biol Date: 2004-09

4. Site-specific modification of Epstein-Barr virus-encoded RNA 1 with N2-benzylguanosine limits the binding sites occupied by PKR.

Authors: Sujiet Puthenveetil; Eduardo A Véliz; Peter A Beal
Journal: Chembiochem Date: 2004-03-05 Impact factor: 3.164

5. siRNA binding proteins of microglial cells: PKR is an unanticipated ligand.

Authors: Zhiren Zhang; Toni Weinschenk; Ketai Guo; Hermann J Schluesener
Journal: J Cell Biochem Date: 2006-04-15 Impact factor: 4.429

6. Molecular basis of double-stranded RNA-protein interactions: structure of a dsRNA-binding domain complexed with dsRNA.

Authors: J M Ryter; S C Schultz
Journal: EMBO J Date: 1998-12-15 Impact factor: 11.598

7. Crystallographic structure of an RNA helix: [U(UA)6A]2.

Authors: A C Dock-Bregeon; B Chevrier; A Podjarny; J Johnson; J S de Bear; G R Gough; P T Gilham; D Moras
Journal: J Mol Biol Date: 1989-10-05 Impact factor: 5.469

8. 2'-amino-modified ribonucleotides as probes for local interactions within RNA.

Authors: James L Hougland; Joseph A Piccirilli
Journal: Methods Enzymol Date: 2009-11-17 Impact factor: 1.600

9. Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6-halo- and 2,6-dihalopurine nucleosides and 2'-deoxynucleosides with acyl or silyl halides.

Authors: Paula Francom; Morris J Robins
Journal: J Org Chem Date: 2003-01-24 Impact factor: 4.354

10. 2-Aminopurine labelled RNA bulge loops. Synthesis and thermodynamics.

Authors: I Zagórowska; R W Adamiak
Journal: Biochimie Date: 1996 Impact factor: 4.079

18 in total

Review 1. Novel modifications in RNA.

Authors: Kelly Phelps; Alexi Morris; Peter A Beal
Journal: ACS Chem Biol Date: 2011-12-23 Impact factor: 5.100

N(2)-Modified 2-aminopurine ribonucleosides as minor-groove-modulating adenosine replacements in duplex RNA.

1. A stepwise huisgen cycloaddition process: copper(I)-catalyzed regioselective "ligation" of azides and terminal alkynes.

2. Structural basis for recognition of the AGNN tetraloop RNA fold by the double-stranded RNA-binding domain of Rnt1p RNase III.

3. The binding selectivity of ADAR2's dsRBMs contributes to RNA-editing selectivity.

4. Site-specific modification of Epstein-Barr virus-encoded RNA 1 with N2-benzylguanosine limits the binding sites occupied by PKR.

5. siRNA binding proteins of microglial cells: PKR is an unanticipated ligand.

6. Molecular basis of double-stranded RNA-protein interactions: structure of a dsRNA-binding domain complexed with dsRNA.

7. Crystallographic structure of an RNA helix: [U(UA)6A]2.

8. 2'-amino-modified ribonucleotides as probes for local interactions within RNA.

9. Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6-halo- and 2,6-dihalopurine nucleosides and 2'-deoxynucleosides with acyl or silyl halides.

10. 2-Aminopurine labelled RNA bulge loops. Synthesis and thermodynamics.

Review 1. Novel modifications in RNA.

2. N-activated β-lactams as versatile reagents for acyl carrier protein labeling.

3. Minor-groove-modulating adenosine replacements control protein binding and RNAi activity in siRNAs.

4. Targeting Base Excision Repair Glycosylases with DNA Containing Transition State Mimics Prepared via Click Chemistry.

Review 5. Chemical modification of siRNA bases to probe and enhance RNA interference.

6. Nucleobase and ribose modifications control immunostimulation by a microRNA-122-mimetic RNA.

7. Synthesis and evaluation of an alkyne-modified ATP analog for enzymatic incorporation into RNA.

8. TLR8 activation and inhibition by guanosine analogs in RNA: Importance of functional groups and chain length.

9. Short interfering RNA guide strand modifiers from computational screening.

10. Base modification strategies to modulate immune stimulation by an siRNA.