Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in 19F NMR

Fluorinated amino acids serve as powerful tools in protein chemistry. We synthesized a series of para-substituted tetrafluorophenylalanines via the regioselective SNAr chemistry of the commercially available pentafluorophenylalanine Boc-Z. These novel unnatural amino acids display distinct 19F NMR s...

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Veröffentlicht in:	Organic letters 2012-01, Vol.14 (2), p.528-531
Hauptverfasser:	Qin, Luoheng, Sheridan, Christopher, Gao, Jianmin
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Sprache:	eng
Schlagworte:	Amino Acids, Aromatic - chemical synthesis Diazonium Compounds - chemistry Fluorine Compounds - chemical synthesis Magnetic Resonance Spectroscopy Molecular Structure
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creator	Qin, Luoheng Sheridan, Christopher Gao, Jianmin
description	Fluorinated amino acids serve as powerful tools in protein chemistry. We synthesized a series of para-substituted tetrafluorophenylalanines via the regioselective SNAr chemistry of the commercially available pentafluorophenylalanine Boc-Z. These novel unnatural amino acids display distinct 19F NMR signatures, making them powerful tools for analyzing protein–membrane interactions with NMR spectroscopy.
doi_str_mv	10.1021/ol203140n
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subjects	Amino Acids, Aromatic - chemical synthesis Diazonium Compounds - chemistry Fluorine Compounds - chemical synthesis Magnetic Resonance Spectroscopy Molecular Structure
title	Synthesis of Tetrafluorinated Aromatic Amino Acids with Distinct Signatures in 19F NMR
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