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

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 a...

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Bibliographic Details
Published inOrganic letters Vol. 23; no. 16; pp. 6288 - 6292
Main Authors Young, Brandon M., Rossi, Paolo, Slavish, P. Jake, Cui, Yixin, Sowaileh, Munia, Das, Jitendra, Kalodimos, Charalampos G., Rankovic, Zoran
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 20.08.2021
Amer Chemical Soc
Subjects
Amino Acids
Chemistry
Chemistry, Organic
Isotope Labeling
Letter
Magnetic Resonance Spectroscopy
Molecular Structure
Phenylalanine - chemistry
Physical Sciences
Proteins
Science & Technology
Tyrosine - chemical synthesis
Tyrosine - chemistry
ACID
REDUCTION
EFFICIENT
PRECURSORS
DEOXYGENATION
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Summary: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.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c02084