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Title: Synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/Se)selenocystine

Abstract

The synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/)selenocystine is described. The starting compound is reduced to (/sup 75/Se)selenocysteine with borohydride and reacted with methyl iodide to form (/sup 75/Se)Se-methyl-selenocysteine, then treated with methyl iodide in formic acid solution to form Se-dimethyl-selenocysteine selenonium iodide. Over a period of days, the selenonium intermediate undergoes spontaneous elimination to form alanine and dimethyl selenide, which reacts with methyl iodide to give the trimethylselenonium product in over 90% yield. 15 references.

Authors:
;
Publication Date:
Research Org.:
Univ. of Wisconsin, Madison
OSTI Identifier:
5696622
Resource Type:
Journal Article
Journal Name:
Anal. Biochem.; (United States)
Additional Journal Information:
Journal Volume: 137:1
Country of Publication:
United States
Language:
English
Subject:
59 BASIC BIOLOGICAL SCIENCES; AMINO ACIDS; REDUCTION; SELENIUM COMPOUNDS; SYNTHESIS; LABELLING; METABOLITES; SELENIUM 75; SELENIUM IODIDES; BETA DECAY RADIOISOTOPES; CARBOXYLIC ACIDS; CHEMICAL REACTIONS; DAYS LIVING RADIOISOTOPES; ELECTRON CAPTURE RADIOISOTOPES; EVEN-ODD NUCLEI; HALIDES; HALOGEN COMPOUNDS; INTERMEDIATE MASS NUCLEI; IODIDES; IODINE COMPOUNDS; ISOTOPES; NUCLEI; ORGANIC ACIDS; ORGANIC COMPOUNDS; RADIOISOTOPES; SELENIUM ISOTOPES; 550201* - Biochemistry- Tracer Techniques

Citation Formats

Foster, S J, and Ganther, H E. Synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/Se)selenocystine. United States: N. p., 1984. Web. doi:10.1016/0003-2697(84)90371-3.
Foster, S J, & Ganther, H E. Synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/Se)selenocystine. United States. https://doi.org/10.1016/0003-2697(84)90371-3
Foster, S J, and Ganther, H E. 1984. "Synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/Se)selenocystine". United States. https://doi.org/10.1016/0003-2697(84)90371-3.
@article{osti_5696622,
title = {Synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/Se)selenocystine},
author = {Foster, S J and Ganther, H E},
abstractNote = {The synthesis of (/sup 75/Se)trimethylselenonium iodide from (/sup 75/)selenocystine is described. The starting compound is reduced to (/sup 75/Se)selenocysteine with borohydride and reacted with methyl iodide to form (/sup 75/Se)Se-methyl-selenocysteine, then treated with methyl iodide in formic acid solution to form Se-dimethyl-selenocysteine selenonium iodide. Over a period of days, the selenonium intermediate undergoes spontaneous elimination to form alanine and dimethyl selenide, which reacts with methyl iodide to give the trimethylselenonium product in over 90% yield. 15 references.},
doi = {10.1016/0003-2697(84)90371-3},
url = {https://www.osti.gov/biblio/5696622}, journal = {Anal. Biochem.; (United States)},
number = ,
volume = 137:1,
place = {United States},
year = {Wed Feb 15 00:00:00 EST 1984},
month = {Wed Feb 15 00:00:00 EST 1984}
}