Sugar-induced conformational changes in boronic acid-appended poly(L- and D-lysine)s and sugar-controlled orientation of a cyanine dye on the polymers

Taro Kimura, Susumu Arimori, Masayuki Takeuchi, Takeshi Nagasaki, Seiji Shinkai

Research output: Contribution to journalArticle

41 Citations (Scopus)

Abstract

Poly(L- and D-lysine)s have been modified with para- or meta-phenylboronic acid derivatives which act as sugar-binding sites (L-1 and D-1 for the para-isomer and L-2 for the meta-isomer). When monosaccharides were added to the L-1 solution, the helix content (monitored by CD spectroscopy) increased and the pH which gives the maximum helix content shifted to a lower pH region. The magnitude of the pH shift was correlated with the affinity of monosaccharides for phenylboronic acid. The pH dependence of the helix content in the presence of D- or L-fructose was similar although a slight difference was seen at the low pH region. This is a novel attempt towards the control of a polypeptide's conformation by sugars. A cyanine dye (4) can be orientated on 1 or 2 in the presence of saccharides. Judging from the CD spectra, the orientation in the presence of 1 is more ordered than that in the presence of 2. The main driving-force for the association of 4 with 1 or 2 is the electrostatic attraction between cationic 4 and the anionic centre developed on the polymer by complexation of the boronic acid residue with saccharides. The chiral orientation of 4 can be monitored by a CD spectroscopic method: it is mainly governed by the chirality of 1 but not by the chirality of saccharides. This is a novel system to control the dye orientation by the cooperative action of naturally- originated α-amino acids and saccharides.

Original languageEnglish
Pages (from-to)1889-1894
Number of pages6
JournalJournal of the Chemical Society, Perkin Transactions 2
Issue number10
DOIs
Publication statusPublished - Dec 1 1995

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Boronic Acids
Monosaccharides
Chirality
Sugars
Isomers
Lysine
Polymers
Coloring Agents
Fructose
Complexation
Conformations
Electrostatics
Binding Sites
Association reactions
Spectroscopy
Derivatives
Amino Acids
Peptides
benzeneboronic acid

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Sugar-induced conformational changes in boronic acid-appended poly(L- and D-lysine)s and sugar-controlled orientation of a cyanine dye on the polymers. / Kimura, Taro; Arimori, Susumu; Takeuchi, Masayuki; Nagasaki, Takeshi; Shinkai, Seiji.

In: Journal of the Chemical Society, Perkin Transactions 2, No. 10, 01.12.1995, p. 1889-1894.

Research output: Contribution to journalArticle

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