Synthesis of a complete set of L-difluorophenylalanines, L-(F2)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor

Tsugumi Fujita; Takeru Nose; Ayami Matsushima; Kazushi Okada; Daisuke Asai; Yasuko Yamauchi; Naoto Shirasu; Takeshi Honda; Daiki Shigehiro; Yasuyuki Shimohigashi

doi:10.1016/S0040-4039(99)02191-7

Synthesis of a complete set of L-difluorophenylalanines, L-(F₂)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor

Tsugumi Fujita, Takeru Nose, Ayami Matsushima, Kazushi Okada, Daisuke Asai, Yasuko Yamauchi, Naoto Shirasu, Takeshi Honda, Daiki Shigehiro, Yasuyuki Shimohigashi

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

18 Citations (Scopus)

Abstract

A complete set of difluorophenylalanines in the L-configuration [L- (F₂)Phe] (namely, L-(2,3-F₂)Phe, L-(2,4-F₂)Phe, L-(2,5-F₂)Phe, L-(2,6- F₂)Phe, L-(3,4-F₂)Phe, L-(3,5-F₂)Phe) was prepared and incorporated into the thrombin receptor-tethered ligand peptide SFLLRNP to identify the phenyl hydrogens of the Phe-2 residue involved in the CH/π receptor interaction. (C) 2000 Elsevier Science Ltd.

Original language	English
Pages (from-to)	923-927
Number of pages	5
Journal	Tetrahedron Letters
Volume	41
Issue number	6
DOIs	https://doi.org/10.1016/S0040-4039(99)02191-7
Publication status	Published - Feb 5 2000

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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Fujita, T., Nose, T., Matsushima, A., Okada, K., Asai, D., Yamauchi, Y., Shirasu, N., Honda, T., Shigehiro, D., & Shimohigashi, Y. (2000). Synthesis of a complete set of L-difluorophenylalanines, L-(F₂)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor. Tetrahedron Letters, 41(6), 923-927. https://doi.org/10.1016/S0040-4039(99)02191-7

Fujita, T, Nose, T , Matsushima, A, Okada, K, Asai, D, Yamauchi, Y, Shirasu, N, Honda, T, Shigehiro, D & Shimohigashi, Y 2000, 'Synthesis of a complete set of L-difluorophenylalanines, L-(F₂)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor', Tetrahedron Letters, vol. 41, no. 6, pp. 923-927. https://doi.org/10.1016/S0040-4039(99)02191-7

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abstract = "A complete set of difluorophenylalanines in the L-configuration [L- (F2)Phe] (namely, L-(2,3-F2)Phe, L-(2,4-F2)Phe, L-(2,5-F2)Phe, L-(2,6- F2)Phe, L-(3,4-F2)Phe, L-(3,5-F2)Phe) was prepared and incorporated into the thrombin receptor-tethered ligand peptide SFLLRNP to identify the phenyl hydrogens of the Phe-2 residue involved in the CH/π receptor interaction. (C) 2000 Elsevier Science Ltd.",

author = "Tsugumi Fujita and Takeru Nose and Ayami Matsushima and Kazushi Okada and Daisuke Asai and Yasuko Yamauchi and Naoto Shirasu and Takeshi Honda and Daiki Shigehiro and Yasuyuki Shimohigashi",

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AU - Fujita, Tsugumi

AU - Nose, Takeru

AU - Matsushima, Ayami

AU - Okada, Kazushi

AU - Asai, Daisuke

AU - Yamauchi, Yasuko

AU - Shirasu, Naoto

AU - Honda, Takeshi

AU - Shigehiro, Daiki

AU - Shimohigashi, Yasuyuki

PY - 2000/2/5

Y1 - 2000/2/5

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AB - A complete set of difluorophenylalanines in the L-configuration [L- (F2)Phe] (namely, L-(2,3-F2)Phe, L-(2,4-F2)Phe, L-(2,5-F2)Phe, L-(2,6- F2)Phe, L-(3,4-F2)Phe, L-(3,5-F2)Phe) was prepared and incorporated into the thrombin receptor-tethered ligand peptide SFLLRNP to identify the phenyl hydrogens of the Phe-2 residue involved in the CH/π receptor interaction. (C) 2000 Elsevier Science Ltd.

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Synthesis of a complete set of L-difluorophenylalanines, L-(F₂)Phe, as molecular explorers for the CH/π interaction between peptide ligand and receptor

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