Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Yasuo Takeuchi; Yoshiyuki Nagao; Kyoko Toma; Yumiko Yoshikawa; Teruaki Akiyama; Hiromi Nishioka; Hitoshi Abe; Takashi Harayama; Shigeo Yamamoto

doi:10.1248/cpb.47.1284

Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Yasuo Takeuchi, Yoshiyuki Nagao, Kyoko Toma, Yumiko Yoshikawa, Teruaki Akiyama, Hiromi Nishioka, Hitoshi Abe, Takashi Harayama, Shigeo Yamamoto

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

10 Citations (Scopus)

Abstract

Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

Original language	English
Pages (from-to)	1284-1287
Number of pages	4
Journal	Chemical and Pharmaceutical Bulletin
Volume	47
Issue number	9
DOIs	https://doi.org/10.1248/cpb.47.1284
Publication status	Published - Sept 1999

Keywords

Dibenzyl citrate
Optical resolution
Siderophore activity
Synthesis
Vibrioferrin

ASJC Scopus subject areas

Chemistry(all)
Drug Discovery

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10.1248/cpb.47.1284

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title = "Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers",

abstract = "Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.",

keywords = "Dibenzyl citrate, Optical resolution, Siderophore activity, Synthesis, Vibrioferrin",

author = "Yasuo Takeuchi and Yoshiyuki Nagao and Kyoko Toma and Yumiko Yoshikawa and Teruaki Akiyama and Hiromi Nishioka and Hitoshi Abe and Takashi Harayama and Shigeo Yamamoto",

year = "1999",

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language = "English",

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pages = "1284--1287",

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T1 - Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

AU - Takeuchi, Yasuo

AU - Nagao, Yoshiyuki

AU - Toma, Kyoko

AU - Yoshikawa, Yumiko

AU - Akiyama, Teruaki

AU - Nishioka, Hiromi

AU - Abe, Hitoshi

AU - Harayama, Takashi

AU - Yamamoto, Shigeo

PY - 1999/9

Y1 - 1999/9

N2 - Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

AB - Total synthesis of vibrioferrin (1), a siderophore, was achieved via a chiral dibenzyl citrate obtained by optical resolution. The citrate moiety of vibrioferrin was determined to have the R configuration and one of the diastereomeric isomers (1b) of 1 did not exhibit siderophore activity.

KW - Dibenzyl citrate

KW - Optical resolution

KW - Siderophore activity

KW - Synthesis

KW - Vibrioferrin

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DO - 10.1248/cpb.47.1284

M3 - Article

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SN - 0009-2363

VL - 47

SP - 1284

EP - 1287

JO - Chemical and Pharmaceutical Bulletin

JF - Chemical and Pharmaceutical Bulletin

IS - 9

ER -

Synthesis and siderophore activity of vibrioferrin and one of its diastereomeric isomers

Abstract

Keywords

ASJC Scopus subject areas

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