43167-40-4Relevant articles and documents
Tryptophan derivatives regulate the seed germination and radicle growth of a root parasitic plant, Orobanche minor
Kuruma, Michio,Suzuki, Taiki,Seto, Yoshiya
supporting information, (2021/05/19)
Root parasitic plant germination is induced by the host-derived chemical, strigolactone (SL). We found that a major microbial culture broth component, tryptone, inhibits the SL-inducible germination of a root parasitic plant, Orobanche minor. L-tryptophan (L-Trp) was isolated as the active compound from tryptone. We further found that L-Trp related compounds (1b-11), such as a major plant hormone auxin (8, indole-3-acetic acid; IAA), also inhibit the germination and post-radicle growth of O. minor. We designed a hybrid chemical (13), in which IAA is attached to a part of SL, and found that this synthetic analog induced the germination of O. minor, and also inhibited post-radicle growth. Moreover, contrary to our expectations, we found that N-acetyl Trp (9) showed germination stimulating activity, and introduction of a substitution at C-5 position increased its activity (12a-12f). Our data, in particular, the discovery of a structurally hybrid compound that has two activities that induce spontaneous germination and inhibit subsequent radical growth, would provide new types of germination regulators for root parasitic plants.
Mechanism for the direct synthesis of tryptophan from indole and serine: A useful NMR technique for the detection of a reactive intermediate in the reaction mixture
Yokoyama, Yuusaku,Nakakoshi, Masamichi,Okuno, Hiroaki,Sakamoto, Yohko,Sakurai, Satoshi
experimental part, p. 811 - 817 (2011/08/22)
The reaction mechanism for the biomimetic synthesis of tryptophan from indole and serine in the presence of Ac2O in AcOH was investigated. Although the time-course 1H-NMR spectra of the reaction of 5-methoxyindole with N-acetylserine were measured in the presence of (CD 3CO)2O in CD3CO2D, 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.
