Chirality control of a Cu(I)·(phenanthroline)2 complex by a sugar-boronic acid interaction. A preliminary step toward the total chain helicity control by a chain-end sugar-binding

Masashi Yamamoto, Masayuki Takeuchi, Seiji Shinkai, Fumito Tani, Yoshinori Naruta

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20 Citations (Scopus)

Abstract

Compounds 1a and 1b which have a 1,10-phenanthroline moiety, were synthesized in order to form a helical structure in the presence of Cu(I), and a boronic acid with which to bind a saccharide at the chain end. When saccharides were added, the Cu(I) complexes (as 1a2·Cu(I) and 1b2·Cu(I)) gave the CD-active species reflecting the absolute configurational structure of saccharides. Thus, the P versus M helicity of the complexes can be controlled by the boronic acid-saccharide interaction. The results show that the terminal boronic acid group is useful to create the chiral helical structure and the total helicity is governed by the chirality of the boronic acid-bound saccharide.

Original languageEnglish
Pages (from-to)9-16
Number of pages8
JournalJournal of the Chemical Society. Perkin Transactions 2
Issue number1
Publication statusPublished - Jan 1 2000

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Boronic Acids
Phenanthrolines
Chirality
Sugars
Sugar Acids

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

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abstract = "Compounds 1a and 1b which have a 1,10-phenanthroline moiety, were synthesized in order to form a helical structure in the presence of Cu(I), and a boronic acid with which to bind a saccharide at the chain end. When saccharides were added, the Cu(I) complexes (as 1a2·Cu(I) and 1b2·Cu(I)) gave the CD-active species reflecting the absolute configurational structure of saccharides. Thus, the P versus M helicity of the complexes can be controlled by the boronic acid-saccharide interaction. The results show that the terminal boronic acid group is useful to create the chiral helical structure and the total helicity is governed by the chirality of the boronic acid-bound saccharide.",
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T1 - Chirality control of a Cu(I)·(phenanthroline)2 complex by a sugar-boronic acid interaction. A preliminary step toward the total chain helicity control by a chain-end sugar-binding

AU - Yamamoto, Masashi

AU - Takeuchi, Masayuki

AU - Shinkai, Seiji

AU - Tani, Fumito

AU - Naruta, Yoshinori

PY - 2000/1/1

Y1 - 2000/1/1

N2 - Compounds 1a and 1b which have a 1,10-phenanthroline moiety, were synthesized in order to form a helical structure in the presence of Cu(I), and a boronic acid with which to bind a saccharide at the chain end. When saccharides were added, the Cu(I) complexes (as 1a2·Cu(I) and 1b2·Cu(I)) gave the CD-active species reflecting the absolute configurational structure of saccharides. Thus, the P versus M helicity of the complexes can be controlled by the boronic acid-saccharide interaction. The results show that the terminal boronic acid group is useful to create the chiral helical structure and the total helicity is governed by the chirality of the boronic acid-bound saccharide.

AB - Compounds 1a and 1b which have a 1,10-phenanthroline moiety, were synthesized in order to form a helical structure in the presence of Cu(I), and a boronic acid with which to bind a saccharide at the chain end. When saccharides were added, the Cu(I) complexes (as 1a2·Cu(I) and 1b2·Cu(I)) gave the CD-active species reflecting the absolute configurational structure of saccharides. Thus, the P versus M helicity of the complexes can be controlled by the boronic acid-saccharide interaction. The results show that the terminal boronic acid group is useful to create the chiral helical structure and the total helicity is governed by the chirality of the boronic acid-bound saccharide.

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