Phenylalanine 4 -azido

In the chemical communication many peptide-protein (e.g., peptide hormone agonist) or protein-protein signaling interaction take place. Various photoreactive amino acids, e.g., azido-phenyalanines (Apa, TFApa) [40, 41], benzoyl-phenyalanines (Bpa,p-OH-Bpa) [41,42],trifluorometil-diazirine-phenylalanine (TMDPhe) [43], were developed (Fig. 3), which can be incorporated into any places in peptide sequences by standard solid-phase synthetic techniques. 

The major requirements for photoactivatable amino acids are that they should exhibit high optical purity and contain appropriate protecting groups for solid-phase synthesis there is also a particular advantage if they contain the radiolabel. While p-azido-phenylalanines can easily be labeled with 125I and... 

Aryl azides are rather bulky groups to append to a ligand, particularly to a small organic molecule, but it has proved possible in many cases to build the reactive group into the structure of a molecule, for instance 8-azido-cAMP and 4-azido-phenylalanine (Fig. 3.2). 

D. S. King, L. Wang, P.G. Schultz, Addition of p-azido-L-phenylalanine to the genetic code of Escherichia coli.J. Am. Chem. Soc. 2002, 124, 9026-9027. 

Graphene can be functionalized via nitrene chemistry as well. Epitaxial graphene (a graphene layer supported on a silicon substrate) can be functionalized with azidotrimethylsilane (09JPCC9433). More recently, azido-phenylalanine 28 was used to functionalize and enhance exfbhation of micrographene sheets to obtain compormd 29 (10CC4097). 

AP)Phe-tRNA is synthesized according to Scheme 1 by coupling the A-hydroxysuccinimide ester of p-azido-A-tBoc-phenylalanine with... 

H)Phe-tRNA (unfractionated). In a standard preparation, 3.5 nmoles of ( H)Phe-tRNA are dissolved in 3.0 ml of 0.2 M triethanolamine-HCl (pH 8.0) or 0.2 M A-2-hydroxyethylpiperazine-A -2-ethanesulfonic acid (HEPES) (pH 8.0), and 600 mg of the A-hydroxysuccinimide ester of p-azido-A-fBoc-phenylalanine in 30 ml of freshly distilled dimethyl sulfoxide are added. The mixture is incubated for 2 hr at 30°, chilled to 0°, and 3.7 ml of 50% dichloroacetic acid are added. After 2 hr at 0°, the mixture is centrifuged and the pellet is washed once with dimethyl-formamide and twice with ethanol. The dried pellet is finally dissolved... 

In 2014, Lewis and coworkers [82] made a significant discovery with the development of the SPAAC for the formation of artificial metaUoenzymes from scaffold proteins containing a /j-azido-L-phenylalanine (Az) residue and catalyticaUy active bicyclononyne-substituted metal complexes ... 

A simple extension of the foregoing synthesis was also shown to be usefrd for making phenylalanine asymmetrically deuterated in the CHD group [68], Azido substituted boronic esters have been mentioned in passing in Section 8.3.5 in conjunction with another synthesis (Scheme 8.22) [54]. 

Considerable progress has been made with the study of substituted derivatives. The L-histidyl-L-histidyl derivative (32), which is a potential enzyme mimic with two recognition sites, has been made from a 6-deoxy-6-iodo-/3-cyclodextrin. A somewhat related pair of substances, 6-N-(N -formyl- )- and L-phenylalanyl)-6-amino-6-deoxy-(3-cyclodextrin, were made from the 6-amino compound and their inclusion behaviour was studied. In similar work the 6-monoazide was partially methylated and reduced, and the amino product was coupled with both enantiomers of N-protected phenylalanine. Other workers have reported the fully O-methylated 6-azido-6-deoxy p-compound. ... 

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