Journal
MAGNETIC RESONANCE IN CHEMISTRY
Volume 48, Issue 10, Pages 811-817Publisher
WILEY-BLACKWELL
DOI: 10.1002/mrc.2676
Keywords
NMR; tryptophan; synthesis; indole; serine; biosynthesis; mechanism; DOSY
Funding
- Ministry of Education, Science, Sports and Culture, Japan (MEXT) [20590014]
- Uehara Memorial Foundation
- Grants-in-Aid for Scientific Research [20590014] Funding Source: KAKEN
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The reaction mechanism for the biomimetic synthesis of tryptophan from indole and serine in the presence of Ac(2)O in AcOH was investigated. Although the time-course (1)H-NMR spectra of the reaction of 5-methoxyindole with N-acetylserine were measured in the presence of (CD(3)CO)(2)O in CD(3)CO(2)D, the reactive intermediate could not be detected. This reaction was conducted without 5-methoxyindole in order to elucidate the reactive intermediate, but the intermediate could not be isolated from the reaction mixture. Since the intermediate would be expected to have a very short life time, and therefore be very difficult to detect by conventional analytical methods, the structure of the intermediate was elucidated using a 2D-NMR technique, diffusion-ordered spectroscopy (DOSY). Two intermediates were detected and confirmed to be 2-methyl-4-methyleneoxazol-5(4H)-one and 2-methyl-4-hydroxymethyloxazol-5(4H)-one. The present results demonstrated that DOSY is a powerful tool for the detection of unstable intermediates. Copyright (C) 2010 John Wiley & Sons, Ltd.
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