73509-22-5Relevant academic research and scientific papers
The cruciferous phytoalexins brassinin and cyclobrassinin are intermediates in the biosynthesis of brassilexin
Soledade,Pedras,Loukaci, Ali,Okanga, Francis I.
, p. 3037 - 3038 (1998)
Following feeding experiments with the tetradeuterated cruciferous phytoalexins brassinin (5b) and cyclobrassinin (6b), leaves of Brassica carinata were elicited with the blackleg causing fungus Phoma lingam and incubated. Spectroscopic and HPLC analyses indicated that both brassinin (5a) and cyclobrassinin (6a) were incorporated into the cruciferous phytoalexin brassilexin (7a).
Rhodium(III)-Catalyzed Direct C7-Selective Alkenylation and Alkylation of Indoles with Maleimides
Sheng, Yaoguang,Gao, Yi,Duan, Bingbing,Lv, Mengxia,Chen, Yao,Yang, Mengjie,Zhou, Jianmin,Liang, Guang,Song, Zengqiang
supporting information, p. 307 - 313 (2021/11/18)
A versatile and efficient method for the coupling of maleimides and indoles at the C7-position has been established under Rh(III) catalysis. The present protocol was compatible with various functional groups, diverse 3-(indol-7-yl)maleimides and 3-(indol-7-yl)succinimides were obtained in moderate to excellent yields by switching reaction conditions. Moreover, this method further highlights the unique practical application for the conjugation with pharmaceutically useful compounds and amino acid derivatives. To explore the mechanism of this transformation, deuteration studies and control experiments have been carried out. (Figure presented.).
Ruthenium(II)-Catalyzed Direct C7-Selective Amidation of Indoles with Dioxazolones at Room Temperature
Sheng, Yaoguang,Zhou, Jianmin,Gao, Yi,Duan, Bingbing,Wang, Yi,Samorodov, Aleksandr,Liang, Guang,Zhao, Qiuhua,Song, Zengqiang
supporting information, p. 2827 - 2839 (2021/02/05)
A protocol for the preparation of 7-amido indoles via regioselective C-H bond functionalization has been first accomplished under Ru(II) catalysis. Indole derivatives and 4-aryl/heteroaryl/benzyl/alkyl dioxzaolines containing various substituents were applicable for this transformation, readily providing the amidated indoles in moderate to good yields. This novel process has many advantages, including good compatibility with diverse functional groups, broad substrate scopes, and mild reaction conditions. Deuteration studies and control experiments have been performed to understand the mechanism of this transformation.
The biosynthetic pathway of crucifer phytoalexins and phytoanticipins: De novo incorporation of deuterated tryptophans and quasi-natural compounds
Pedras, M. Soledade C.,Okinyo-Owiti, Denis P.,Thoms, Ken,Adio, Adewale M.
experimental part, p. 1129 - 1138 (2010/06/21)
Although several biosynthetic intermediates in pathways to cruciferous phytoalexins and phytoanticipins are common, questions regarding the introduction of substituents at N-1 of the indole moiety remain unanswered. Toward this end, we investigated the potential incorporations of several perdeuterated d- and l-1′-methoxytryptophans, d- and l-tryptophans and other indol-3-yl derivatives into pertinent phytoalexins and phytoanticipins (indolyl glucosinolates) produced in rutabaga (Brassica napus L. ssp. rapifera) roots. In addition, we probed the potential transformations of quasi-natural compounds, these being analogues of biosynthetic intermediates that might lead to "quasi-natural" products (products similar to natural products but not produced under natural conditions). No detectable incorporations of deuterium labeled 1′-methoxytryptophans into phytoalexins or glucobrassicin were detected. l-tryptophan was incorporated in a higher percentage than d-tryptophan into both phytoalexins and phytoanticipins. However, in the case of the phytoalexin rapalexin A, both d- and l-tryptophan were incorporated to the same extent. Furthermore, the transformations of both 1′-methylindolyl-3′-acetaldoxime and 1′-methylindolyl-3′-acetothiohydroxamic acid (quasi-natural products) into 1′-methylglucobrassicin but not into phytoalexins suggested that post-aldoxime enzymes in the biosynthetic pathway of indolyl glucosinolates are not substrate-specific. Hence, it would appear that the 1-methoxy substituent of the indole moiety is introduced downstream from tryptophan and that the post-aldoxime enzymes of the glucosinolate pathway are different from the enzymes of the phytoalexin pathway. A higher substrate specificity of some enzymes of the phytoalexin pathway might explain the relatively lower structural diversity among phytoalexins than among glucosinolates.
Syntheses of perdeuterated indoles and derivatives as probes for the biosyntheses of crucifer phytoalexins
Pedras, M. Soledade C.,Okinyo, Denis P. O.
, p. 33 - 45 (2007/10/03)
A simple two-step preparation of [2H4]indole, a starting material necessary for the synthesis of various crucifer metabolites, starting with readily available 1H NMR solvent [2H 5]nitrobenzene (99% de
