THE CHEMISTRY OF 1-HYDROXYINDOLES : SYNTHESES OF METHYL 1-HYDROXYINDOLE-3-ACETATE, N__-B-ACETYL-1-HYDROXY-TRYPTAMINE, (±)- AND (S__-)-1-HYDROXYTRYPTOPHAN DERIVATIVES

Masanori SOMEI; Toshiya KAWASAKI; Kazuhisa SHIMIZU; Yoshikazu FUKUI; Toshiharu OHTA

doi:10.1248/cpb.39.1905

Masanori SOMEI, Toshiya KAWASAKI, Kazuhisa SHIMIZU, Yoshikazu FUKUI, Toshiharu OHTA

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Keywords: methyl 1-hydroxyindole-3-acetate, (±)-2-acetoamino-3-(1-hydroxyindol-3-yl)-propanol, N__-b-acetyl-1-hydroxytryptamine, (±)-N__-b-acetyl-1-hydroxytryptophan methyl ester, (S__-)-(+)-N__-b-acetyl-1-hydroxytryptophan methyl ester, 1-hydroxyindole, 2, 3-dihydroindole, oxidation, X-ray crystallographic analysis, tryptophan

JOURNAL FREE ACCESS

1991 Volume 39 Issue 7 Pages 1905-1907

DOI https://doi.org/10.1248/cpb.39.1905

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Abstract

Methyl 1-hydroxyindole-3-acetate, (±)-2-acetoamino-3-(10hydroxyindol-3-yl)propanol, N__-b-acetyl-1-hydroxytryptamine, (±)- and (S__-)-(+)-N__-b-acetyl-1-hydroxytryptophan methyl ester, which are needed for inspecting our hypothesis regarding the metabolism of tryptophan, were prepared for the first time. The structural proof of (±)-N__-b-acetyl-1-hydroxytryptophan methyl ester by X-ray crysatllographic analysis is also reported.

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