Syntheses of Pyrroloquinoline Quinone Derivatives: Model Compounds of a Novel Coenzyme PQQ (Methoxatin)

Shinobu Itoh; Jin-ichiro Kato; Teruhisa Inoue; Yutaka Kitamura; Mitsuo Komatsu; Yoshiki Ohshiro

doi:10.1055/s-1987-28172

Synthesis 1987; 1987(12): 1067-1071
DOI: 10.1055/s-1987-28172

paper

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Syntheses of Pyrroloquinoline Quinone Derivatives: Model Compounds of a Novel Coenzyme PQQ (Methoxatin)

Shinobu Itoh^* , Jin-ichiro Kato, Teruhisa Inoue, Yutaka Kitamura, Mitsuo Komatsu, Yoshiki Ohshiro

^*Department of Applied Chemistry, Faculty of Engineering, Osaka University, Yamadaoka 2-1, Suita, Osaka 565, Japan

Abstract

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Pyrroloquinoline quinone derivatives were synthesized as model compounds of a novel coenzyme PQQ. The 2-mono- and 2,9-dicarboxylic acid derivatives 1b and 1d and the 1-methylated derivative If were synthesized relatively easily from the intermediates 5 and 4 of the PQQ-synthesis. The 2, 7-dicarboxylic acid derivative 1e was also synthesized via a combination of the Japp-Klingemann reaction and Fischer indolization.

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