Discrimination between glucose-1-phosphate and glucose-6-phosphate with a boronic-acid-appended metalloporphyrin

Tomoyuki Imada; Hideomi Kijima; Masayuki Takeuchi; Seiji Shinkai

doi:10.1016/0040-4039(95)00218-2

Discrimination between glucose-1-phosphate and glucose-6-phosphate with a boronic-acid-appended metalloporphyrin

Tomoyuki Imada, Hideomi Kijima, Masayuki Takeuchi, Seiji Shinkai

Research output: Contribution to journal › Article › peer-review

23 Citations (Scopus)

Abstract

When D-glucose-6-phosphate (G-6-P) is bound to boronic-acid-appended zinc(II) porphyrin (2), the δp value in ³¹P NMR spectroscopy markedly shifts to higher magnetic field and a strong exciton-coupling band appears in CD spectroscopy. Such large changes are not observable for 2 plus D-glucose, 2 plus α-D-glucose-1-phosphate (G-1-P), and for boronic-acid-appended porphyrin (free base: 1) plus these glucose derivatives. This is first example that G-1-P and G-6-P are successfully discriminated by an artificial receptor.

Original language	English
Pages (from-to)	2093-2096
Number of pages	4
Journal	Tetrahedron Letters
Volume	36
Issue number	12
DOIs	https://doi.org/10.1016/0040-4039(95)00218-2
Publication status	Published - Mar 20 1995
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(95)00218-2

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title = "Discrimination between glucose-1-phosphate and glucose-6-phosphate with a boronic-acid-appended metalloporphyrin",

abstract = "When D-glucose-6-phosphate (G-6-P) is bound to boronic-acid-appended zinc(II) porphyrin (2), the δp value in 31P NMR spectroscopy markedly shifts to higher magnetic field and a strong exciton-coupling band appears in CD spectroscopy. Such large changes are not observable for 2 plus D-glucose, 2 plus α-D-glucose-1-phosphate (G-1-P), and for boronic-acid-appended porphyrin (free base: 1) plus these glucose derivatives. This is first example that G-1-P and G-6-P are successfully discriminated by an artificial receptor.",

author = "Tomoyuki Imada and Hideomi Kijima and Masayuki Takeuchi and Seiji Shinkai",

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T1 - Discrimination between glucose-1-phosphate and glucose-6-phosphate with a boronic-acid-appended metalloporphyrin

AU - Imada, Tomoyuki

AU - Kijima, Hideomi

AU - Takeuchi, Masayuki

AU - Shinkai, Seiji

PY - 1995/3/20

Y1 - 1995/3/20

N2 - When D-glucose-6-phosphate (G-6-P) is bound to boronic-acid-appended zinc(II) porphyrin (2), the δp value in 31P NMR spectroscopy markedly shifts to higher magnetic field and a strong exciton-coupling band appears in CD spectroscopy. Such large changes are not observable for 2 plus D-glucose, 2 plus α-D-glucose-1-phosphate (G-1-P), and for boronic-acid-appended porphyrin (free base: 1) plus these glucose derivatives. This is first example that G-1-P and G-6-P are successfully discriminated by an artificial receptor.

AB - When D-glucose-6-phosphate (G-6-P) is bound to boronic-acid-appended zinc(II) porphyrin (2), the δp value in 31P NMR spectroscopy markedly shifts to higher magnetic field and a strong exciton-coupling band appears in CD spectroscopy. Such large changes are not observable for 2 plus D-glucose, 2 plus α-D-glucose-1-phosphate (G-1-P), and for boronic-acid-appended porphyrin (free base: 1) plus these glucose derivatives. This is first example that G-1-P and G-6-P are successfully discriminated by an artificial receptor.

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JO - Tetrahedron Letters

JF - Tetrahedron Letters

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ER -

Discrimination between glucose-1-phosphate and glucose-6-phosphate with a boronic-acid-appended metalloporphyrin

Abstract

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