Synthesis of chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines and spermidines. Elucidation of the stereochemical course of putrescine aminopropyltransferase (spermidine synthase) was written by Orr, Gary R.;Danz, Deborah W.;Pontoni, Gabriele;Prabhakaran, P. C.;Gould, Steven J.;Coward, James K.. And the article was included in Journal of the American Chemical Society in 1988.SDS of cas: 3130-75-4 This article mentions the following:
The stereochem. course of enzyme-catalyzed aminopropyl transfer was investigated. The stereospecific synthesis of chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines and several chirally deuteriated spermidine (-)-camphanamide derivatives allowed the elucidation of aminopropyltransferase stereochem. by using 1H NMR techniques. Putrescine aminopropyltransferase (spermidine synthase) isolated from Escherichia聽coli catalyzed the synthesis of chirally deuteriated spermidines from 1,4-diaminobutane (putrescine) and chirally deuteriated (S-adenosyl-S-methylsulfonio)propylamines. Derivatization of the biosynthetic spermidines to 1,8-bis-(tert-butoxycarbonyl)spermidine (-)-camphanamides and comparison of their 1H NMR spectra with those of the synthetic standards permits determination of the absolute configuration of the biosynthetic products. The results show that the reaction catalyzed by E. coli spermidine synthase proceeds with inversion of configuration at the methylene carbon undergoing nucleophilic attack by putrescine. These data support a single-displacement mechanism proceeding via a ternary complex of enzyme and both substrates. In the experiment, the researchers used many compounds, for example, 4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4SDS of cas: 3130-75-4).
4-(1,3-Dioxoisoindolin-2-yl)butanoic acid (cas: 3130-75-4) belongs to indole derivatives. Indole is an important structural motif of various drugs, therapeutic leads besides its prevalence in numerous natural products, agrochemicals, perfumery, and dyes. In addition to indole, the strain-release chemistry worked for numerous substrates including amines, alcohols, thiols, carboxylic acids, imidazoles, and pyrazoles.SDS of cas: 3130-75-4
Referemce:
Indole alkaloid derivatives as building blocks of natural products from聽Bacillus thuringiensis聽and聽Bacillus velezensis聽and their antibacterial and antifungal activity study,
Preparation of Indole Containing Building Blocks for the Regiospecific Construction of Indole Appended Pyrazoles and Pyrroles