α-Ketoacids as precursors for phenylalanine and tyrosine labelling in cell-based protein overexpression

Akira K, Hasegawa H, Baba S (1995) Synthesis of selectively 13C labelled benzoic acid for nuclear magnetic resonance. J Label Compd Radiopharm 36:845–853 Ayala I, Sounier R, Usé N, Gans P, Boisbouvier J (2009) An efficient protocol for the complete incorporation of methyl-protonated alanine in perdeuterated protein. J Biomol NMR 43:111–119 Billek G (1961a) Eine neue Synthese der 4-Hydroxyphenylbrenztraubensäure. Monatsh Chem 92:335–342 Billek G (1961b) Zur Synthese der Phenylbrenztraubensäuren, 3. Mitt Monatsh Chem 92:343–351 Billek G (1961c) Über die Kondensation aromatischer Aldehyde mit Hydantoin. Monatsh Chem 92:352–360 Bogan AA, Thorn KS (1998) Anatomy of hot spots in protein interfaces. J Mol Biol 280:1–9 Fischer M, Kloiber K, Hauesler J, Ledolter K, Konrat R, Schmid W (2007) Synthesis of a 13C-methyl-group-labeled methionine precursor as a useful tool for simplifying protein structural analysis by NMR spectroscopy. ChemBioChem 8:610–612 Goto NK, Gardner KH, Mueller GA, Willis KC, Kay LE (1999) A robust and cost-effective method for the production of Val, Leu, Ile (δ1) methyl-protonated 15 N-, 13C-, 2H-labeled proteins. J Biomol NMR 13:369–374 Hoogstraten CG, Johnson JE Jr (2008) Metabolic labeling: taking advantage of bacterial pathways to prepare spectroscopically useful isotope patterns in proteins and nucleic acids. Concepts Magn Reson A 32A:34–55 Kainosho M, Torizawa T, Iwashita Y, Terauchi T, Ono AM, Güntert P (2006) Optimal isotope labelling for NMR protein structure determinations. Nature 440:52–57 Kasinath V, Valentine KG, Wand AJ (2013) A 13C labeling strategy reveals a range of aromatic side chain motion in calmodulin. J Am Chem Soc 135:9560–9563 Lee KM, Androphy EJ, Baleja JD (1995) A novel method for selective isotope labeling of bacterially expressed proteins. J Biomol NMR 5:93–96 LeMaster DM, Kushlan DM (1996) Dynamical mapping of E. coli thioredoxin via 13C NMR relaxation analysis. J Am Chem Soc 118:9255–9264 Lichtenecker R, Ludwiczek ML, Schmid W, Konrat R (2004) Simplification of protein NOESY spectra using bioorganic precursor synthesis and NMR spectral editing. J Am Chem Soc 126:5348–5349 Lichtenecker RJ, Coudevylle N, Konrat R, Schmid W (2013) Selective isotope labelling of leucine residues by using α-ketoacid precursor compounds. ChemBioChem 14:818–821 Lin Z, Xu Y, Yang S, Yang D (2006) Sequence-specific assignment of aromatic resonances of uniformly 13C,15N-labeled proteins by using 13C- and 15N-edited NOESY spectra. Angew Chem 118:1994–1997 Löhr F, Hänsel R, Rogov VV, Dötsch V (2007) Improved pulse sequences for sequence specific assignment of aromatic proton resonances in proteins. J Biomol NMR 37:205–224 Raap J, Niewenhuis S, Creemers A, Hexspoor S, Kragl U, Lugtenburg J (1999) Synthesis of Isotopically Labelled l-Phenylalanine and l-Tyrosine. Eur J Org Chem 2609–2621 Rajesh S, Nietlispach D, Nakayama H, Takio K, Laue ED, Shibata T, Ito Y (2003) A novel method for the biosynthesis of deuterated proteins with selective protonation at the aromatic rings of Phe, Tyr and Trp. J Biomol NMR 27:81–86 Rasia RM, Brutscher B, Plevin MJ (2012) Selective isotopic unlabeling of proteins using metabolic precursors: application to NMR assignment of intrinsically disordered proteins. ChemBioChem 13:732–739 Slupsky CM, Gentile LN, McIntosh LP (1998) Assigning the NMR spectra of aromatic amino acids in proteins: analysis of two Ets pointed domains. Biochem Cell Biol 76:379–390 Staunton D, Schlinkert R, Zanetti G, Colebrook SA, Campbell ID (2006) Cell-free expression and selective isotope labelling in protein NMR. Magn Reson Chem 44:S2–S9 Takeda M, Ono AM, Terauchi T, Kainosho M (2010) Application of SAIL phenylalanine and tyrosine with alternative isotope-labeling patterns for protein structure determination. J Biomol NMR 46:45–49 Teilum K, Brath U, Lundström P, Akke M (2006) Biosynthetic 13C labeling of aromatic side chains in proteins for NMR relaxation measurements. J Am Chem Soc 128:2506–2507 Torizawa T, Ono AM, Terauchi T, Kainosho M (2005) NMR assignment methods for the aromatic ring resonances of phenylalanine and tyrosine residues in proteins. J Am Chem Soc 127:12620–12626 Wang H, Janowick DA, Schkeryantz JM, Liu X, Fesik SWJ (1999) A method of assigning phenylalanines in proteins. J Am Chem Soc 121:1611–1612