Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method

Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method

Mosher amides of α-methylselenocysteine were synthesized to determine the absolute stereochemistry of the sterically hindered α-carbon utilizing 1H, 13C, 19F, and 77Se NMR spectroscopies. After analysis of these spectra using the established Mosher method, the stereochemistry of the α-carbon was det...

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Bibliographic Details
Main Authors: Robert J. Wehrle, Douglas R. Powell, Douglas S. Masterson
Format: Article
Language:English
Published: Elsevier 2021-01-01
Series:Results in Chemistry
Subjects:
Unnatural amino acids
Mosher analysis
NMR
Determination of stereochemistry
Online Access:http://www.sciencedirect.com/science/article/pii/S2211715621000199
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spelling doaj-b235015dfd7b4f3fb17af3b729a1d6da2021-02-27T04:38:22ZengElsevierResults in Chemistry2211-71562021-01-013100114Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher methodRobert J. Wehrle0Douglas R. Powell1Douglas S. Masterson2School of Mathematics and Natural Sciences, Chemistry and Biochemistry, University of Southern Mississippi, 118 College Drive #5043, Hattiesburg, MS 39406, United StatesSmall Molecule Crystallography Lab, Department of Chemistry and Biochemistry, University of Oklahoma, 101 Stephenson Parkway, Norman, OK 73019-5251, United StatesSchool of Mathematics and Natural Sciences, Chemistry and Biochemistry, University of Southern Mississippi, 118 College Drive #5043, Hattiesburg, MS 39406, United States; Corresponding author.Mosher amides of α-methylselenocysteine were synthesized to determine the absolute stereochemistry of the sterically hindered α-carbon utilizing 1H, 13C, 19F, and 77Se NMR spectroscopies. After analysis of these spectra using the established Mosher method, the stereochemistry of the α-carbon was determined to be (R), which was subsequently confirmed using x-ray crystallography.http://www.sciencedirect.com/science/article/pii/S2211715621000199Unnatural amino acidsMosher analysisNMRDetermination of stereochemistry
collection DOAJ
language English
format Article
sources DOAJ
author Robert J. Wehrle
Douglas R. Powell
Douglas S. Masterson
spellingShingle Robert J. Wehrle
Douglas R. Powell
Douglas S. Masterson
Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
Results in Chemistry
Unnatural amino acids
Mosher analysis
NMR
Determination of stereochemistry
author_facet Robert J. Wehrle
Douglas R. Powell
Douglas S. Masterson
author_sort Robert J. Wehrle
title Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
title_short Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
title_full Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
title_fullStr Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
title_full_unstemmed Direct determination of absolute stereochemistry of α-methylselenocysteine using the Mosher method
title_sort direct determination of absolute stereochemistry of α-methylselenocysteine using the mosher method
publisher Elsevier
series Results in Chemistry
issn 2211-7156
publishDate 2021-01-01
description Mosher amides of α-methylselenocysteine were synthesized to determine the absolute stereochemistry of the sterically hindered α-carbon utilizing 1H, 13C, 19F, and 77Se NMR spectroscopies. After analysis of these spectra using the established Mosher method, the stereochemistry of the α-carbon was determined to be (R), which was subsequently confirmed using x-ray crystallography.
topic Unnatural amino acids
Mosher analysis
NMR
Determination of stereochemistry
url http://www.sciencedirect.com/science/article/pii/S2211715621000199
work_keys_str_mv AT robertjwehrle directdeterminationofabsolutestereochemistryofamethylselenocysteineusingthemoshermethod
AT douglasrpowell directdeterminationofabsolutestereochemistryofamethylselenocysteineusingthemoshermethod
AT douglassmasterson directdeterminationofabsolutestereochemistryofamethylselenocysteineusingthemoshermethod
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