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Orthogonal protection of L-Tyrosine (Protecting groups are marked in blue, the amino acid is shown in black).(1) Fmoc-protected amino group, (2) benzyl ester protected carboxyl group and (3) tert-butyl ether protected phenolic hydroxyl group of Tyrosine.
L-Tyrosine or tyrosine (symbol Tyr or Y) [2] or 4-hydroxyphenylalanine is one of the 20 standard amino acids that are used by cells to synthesize proteins. It is a conditionally essential amino acid with a polar side group .
The fluorenylmethoxycarbonyl protecting group (Fmoc) is a base-labile amine protecting group used in organic synthesis, particularly in peptide synthesis [1]. It is popular for its stability toward acids and hydrolysis and its selective removal by weak bases, such as piperidine , without affecting most other protecting groups or sensitive ...
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l-DOPA is produced from the amino acid l-tyrosine by the enzyme tyrosine hydroxylase. l-DOPA can act as an l-tyrosine mimetic and be incorporated into proteins by mammalian cells in place of l-tyrosine, generating protease-resistant and aggregate-prone proteins in vitro and may contribute to neurotoxicity with chronic l-DOPA administration. [10]
The tyrosine–tyrosine crosslink can form by ultraviolet irradiation and other conditions that induce radical formation. [4] Proteins with calcium binding sites consisting of two tyrosine residues, such as calmodulin and troponin C, are especially prone to this reaction as a result of coordination of their phenol groups to a calcium ion.
In the second, mild protection scheme, A and dA are protected with isobutyryl [28] or phenoxyacetyl groups (PAC). [29] C and dC bear acetyl protection, [27] and G and dG are protected with 4-isopropylphenoxyacetyl (i-Pr-PAC) [30] or dimethylformamidino (dmf) [31] groups. Mild protecting groups are removed more readily than the standard ...
The N-terminal domain of tyrosyl-tRNA synthetase provides the chemical groups necessary for converting the substrates tyrosine and ATP into a reactive intermediate, tyrosyl-adenylate (the first step of the aminoacylation reaction) and for transferring the amino-acid moiety from tyrosyl-adenylate to the 3'OH-CCA terminus of the cognate tRNA(Tyr ...