Organization of nucleosides supported by boronic-acid-appended poly(L-lysine)

Creation of a novel RNA mimic

H. Kobayashi, M. Amaike, K. Koumoto, Seiji Shinkai

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Boronic-acid-appended poly(L-lysine) (1) can form anionic boronate esters with diol derivatives in aqueous solution. One can thus expect that when nucleosides are mixed with 1, the resultant complexes will satisfy the basic structural characteristics of RNA, viz., one-dimensionally organized nucleic bases and anionic charges. To obtain insights into this novel RNA mimic, the solution properties of adenosine (Ad) were estimated in the absence and the presence of 1. The large absorption and CD spectral changes were observed at pH 6-10 where the poly(L-lysine) main chain tends to adopt an α-helix-rich conformation. On the basis of the fact that the magnitude of the spectral changes is much larger than the fraction of complexed Ad molecules, the polymer-supported organization mode was proposed: that is, Ad molecules complexed by covalent bonds with 1 act as clusters to induce further organization of uncomplexed Ad molecules by noncovalent interactions. The proposal was further confirmed by 1H NMR spectroscopy and dynamic light scattering. On the other hand, none of these spectral changes were observed for 2′-deoxyadenosine. The 1-Ad complex thus formed can interact with complementary poly(U) but not with noncomplementary poly(C), indicating that it can act as a novel RNA mimic.

Original languageEnglish
Pages (from-to)1311-1317
Number of pages7
JournalBulletin of the Chemical Society of Japan
Volume74
Issue number7
DOIs
Publication statusPublished - Jul 1 2001

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Boronic Acids
Nucleosides
Adenosine
Lysine
RNA
Molecules
Poly C
Poly U
Covalent bonds
Dynamic light scattering
Nuclear magnetic resonance spectroscopy
Conformations
Polymers
Esters
Derivatives

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Organization of nucleosides supported by boronic-acid-appended poly(L-lysine) : Creation of a novel RNA mimic. / Kobayashi, H.; Amaike, M.; Koumoto, K.; Shinkai, Seiji.

In: Bulletin of the Chemical Society of Japan, Vol. 74, No. 7, 01.07.2001, p. 1311-1317.

Research output: Contribution to journalArticle

Kobayashi, H. ; Amaike, M. ; Koumoto, K. ; Shinkai, Seiji. / Organization of nucleosides supported by boronic-acid-appended poly(L-lysine) : Creation of a novel RNA mimic. In: Bulletin of the Chemical Society of Japan. 2001 ; Vol. 74, No. 7. pp. 1311-1317.
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