Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications

[Image: see text] Isotopically labeled amino acids are widely used to study the structure and dynamics of proteins by NMR. Herein we describe a facile, gram-scale synthesis of compounds 1b and 2b under standard laboratory conditions from the common intermediate 7. 2b is obtained via simple deprotect...

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Autores principales: Young, Brandon M., Rossi, Paolo, Slavish, P. Jake, Cui, Yixin, Sowaileh, Munia, Das, Jitendra, Kalodimos, Charalampos G., Rankovic, Zoran
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2021
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8884888/
https://www.ncbi.nlm.nih.gov/pubmed/34379431
http://dx.doi.org/10.1021/acs.orglett.1c02084
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author Young, Brandon M.
Rossi, Paolo
Slavish, P. Jake
Cui, Yixin
Sowaileh, Munia
Das, Jitendra
Kalodimos, Charalampos G.
Rankovic, Zoran
author_facet Young, Brandon M.
Rossi, Paolo
Slavish, P. Jake
Cui, Yixin
Sowaileh, Munia
Das, Jitendra
Kalodimos, Charalampos G.
Rankovic, Zoran
author_sort Young, Brandon M.
collection PubMed
description [Image: see text] Isotopically labeled amino acids are widely used to study the structure and dynamics of proteins by NMR. Herein we describe a facile, gram-scale synthesis of compounds 1b and 2b under standard laboratory conditions from the common intermediate 7. 2b is obtained via simple deprotection, while 1b is accessed through a reductive deoxygenation/deuteration sequence and deprotection. 1b and 2b provide improved signal intensity using lower amounts of labeled precursor and are alternatives to existing labeling approaches.
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spelling pubmed-88848882022-02-28 Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications Young, Brandon M. Rossi, Paolo Slavish, P. Jake Cui, Yixin Sowaileh, Munia Das, Jitendra Kalodimos, Charalampos G. Rankovic, Zoran Org Lett [Image: see text] Isotopically labeled amino acids are widely used to study the structure and dynamics of proteins by NMR. Herein we describe a facile, gram-scale synthesis of compounds 1b and 2b under standard laboratory conditions from the common intermediate 7. 2b is obtained via simple deprotection, while 1b is accessed through a reductive deoxygenation/deuteration sequence and deprotection. 1b and 2b provide improved signal intensity using lower amounts of labeled precursor and are alternatives to existing labeling approaches. American Chemical Society 2021-08-11 2021-08-20 /pmc/articles/PMC8884888/ /pubmed/34379431 http://dx.doi.org/10.1021/acs.orglett.1c02084 Text en © 2021 The Authors. Published by American Chemical Society https://creativecommons.org/licenses/by-nc-nd/4.0/Permits non-commercial access and re-use, provided that author attribution and integrity are maintained; but does not permit creation of adaptations or other derivative works (https://creativecommons.org/licenses/by-nc-nd/4.0/).
spellingShingle Young, Brandon M.
Rossi, Paolo
Slavish, P. Jake
Cui, Yixin
Sowaileh, Munia
Das, Jitendra
Kalodimos, Charalampos G.
Rankovic, Zoran
Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications
title Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications
title_full Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications
title_fullStr Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications
title_full_unstemmed Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications
title_short Synthesis of Isotopically Labeled, Spin-Isolated Tyrosine and Phenylalanine for Protein NMR Applications
title_sort synthesis of isotopically labeled, spin-isolated tyrosine and phenylalanine for protein nmr applications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC8884888/
https://www.ncbi.nlm.nih.gov/pubmed/34379431
http://dx.doi.org/10.1021/acs.orglett.1c02084
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