Of phenylalanine

As an example, the empirical formula of phenylalanine may be split into a more extended form that shows the presence of a phenyl ring, as well as an amino and a carboxylic acid group (the condensed form in Figure 2-4). 

Figure 2-7. Different tine notations for the structure diagram of phenylalanine,...

Figure 2-42. The Morgan Algorithm generates an unambiguous and unique numbering of phenylalanine (see Tutorial, Section 2,S,J,1).

In this simplified example of phenylalanine, in the first iteration the methyl groups arc given a value of I in the first classification step because they contain a primaiy C-atom, The methylene group obtains a value of 2, and the methine carbon atom a value of 3. In the second step, the carbon atom of the methyl group on the left-hand side obtains an extended connectivity (EC) value of 2 because its neighboring atom had a value of 2 in the first classification step. 

Figure 2-44, The EC values of the atoins of phenylalanine (without hydrogens) are calculated by considering the class values of the neighboring atoms, After each relaKatlon process, c, the number of equivalent classes (different EC values), is determined.

Figure2-116. Graphical representations of molecular surfaces of phenylalanine a) dots b) mesh or chicken-wire c) solid d) semi-transparent,...

Figure 2-123. The most coinmon molecular graphics representations of phenylalanine a) wire frame b) capped sticks c) balls and sticks d) space-filling.

Figure 2-125. Different isovalue-based surfaces of phenylalanine a) isoelectronic density b) molecular orbitals (HOMO-LUMO) c) isopotential surface and d) isosurface of the electron cryo-microscopic volume of the ribosome of Escherichia coii.

The control solution (B) is used in this experiment to differentiate between the blue spots of glycine and phenylalanine. It will be seen that the Rp value of phenylalanine is greater than that of glycine. 

As a p hydroxy derivative of phenylalanine tyrosine has properties similar to those of phenylalanine plus the ability to engage m hydrogen bonding via its —OH group Asparagine and glutamine are not amines they are amides The side chains of both O... 

Transfer RNA (tRNA) Transfer RNAs are relatively small nucleic acids containing only about 70 nucleotides They get their name because they transfer ammo acids to the ribosome for incorporation into a polypeptide Although 20 ammo acids need to be transferred there are 50-60 tRNAs some of which transfer the same ammo acids Figure 28 11 shows the structure of phenylalanine tRNA (tRNA ) Like all tRNAs it IS composed of a single strand with a characteristic shape that results from the presence of paired bases m some regions and their absence m others... 

The 1968 Nobel Prize in physiology or medicine was shared by Robert W Holley of Cornell University for determining the nucleotide sequence of phenylalanine transfer RNA... 

Chymotrypsin (Section 27 10) A digestive enzyme that cat alyzes the hydrolysis of proteins Chymotrypsin selectively catalyzes the cleavage of the peptide bond between the car boxyl group of phenylalanine tyrosine or tryptophan and some other ammo acid... 

The sequence of each different peptide or protein is important for understanding the activity of peptides and proteins and for enabling their independent synthesis, since the natural ones may be difficult to obtain in small quantities. To obtain the sequence, the numbers of each type of amino acid are determined by breaking down the protein into its individual amino acids using concentrated acid (hydrolysis). For example, hydrolysis of the tetrapeptide shown in Figure 45.3 would give one unit of glycine, two units of alanine, and one unit of phenylalanine. Of course, information as to which amino acid was linked to which others is lost. 

Cystic fibrosis, a disease of the Caucasian population, is associated with defective CL regulation and is essentially a disorder of epithehal cells (113,114). The defect arises at several levels in the CL ion transporter, ie, the cystic fibrosis transmembrane regulation (CFTR), and is associated with defective CL transport and defective processing, whereby the protein is not correctiy incorporated into the cell membrane. The most common mutation, affecting approximately 60% of patients, is termed F 608 and designates the loss of phenylalanine at this position. This mutation appears to be at least 50,000 years old, which suggests that its survival may have had evolutionary significance (115). 

In the case of hyperphenylalaninaemia, which occurs ia phenylketonuria because of a congenital absence of phenylalanine hydroxylase, the observed phenylalanine inhibition of proteia synthesis may result from competition between T.-phenylalanine and L-methionine for methionyl-/RNA. Patients sufferiag from maple symp urine disease, an inborn lack of branched chain oxo acid decarboxylase, are mentally retarded unless the condition is treated early enough. It is possible that the high level of branched-chain amino acids inhibits uptake of L-tryptophan and L-tyrosiae iato the brain. Brain iajury of mice within ten days after thek bkth was reported as a result of hypodermic kijections of monosodium glutamate (MSG) (0.5—4 g/kg). However, the FDA concluded that MSG is a safe kigredient, because mice are bom with underdeveloped brains regardless of MSG kijections (106). 

Finally, a quinonoid 6,7,8-trihydropterin structure (49) absorbing at 303 nm plays an important role as a labile intermediate in the tetrahydrobiopterin-dependent enzymatic hydroxylation of phenylalanine <67JBC(242)3934). 

Pyrimidine-2,4-diamine, 5-(benzylamino)-6-hydroxy-as cofactor of phenylalanine hydroxylase, 1, 261 Pyrimidine-2,4-diamine, 5-ethoxy-synthesis, 3, 114... 

Cleavage occurs with acid. The following tables give relative rate data that are useful for comparing other, more commonly employed, derivatives of phenylalanine (Phe). 

This azlactone is prepared readily from benzaldehyde according to the procedure given for the azlactone of a-ben-zoylamino-/3-(3,4-dimethoxyphenyl)-acrylic acid (Org. Syn. 13, 8). From 53 g. (0.5 mole) of benzaldehyde, 89.5 g. (0.5 mole) of hippuric acid, 41 g. of fused sodium acetate, and 153 g. of acetic anhydride there is obtained 78-80 g. (62-64 per cent yield) of an almost pure product melting at 165-166° (corr.). This material is sufficiently pure for use in the preparation of phenylalanine. By crystallization from 150 cc. of benzene a product melting at 167-168° (corr.) is obtained. 

To direct the synthesis so that only Phe-Gly is formed, the amino group of phenylalanine and the car boxyl group of glycine must be protected so that they cannot react under the conditions of peptide bond formation. We can represent the peptide bond formation step by the following equation, where X and Y are amine- and carboxyl-protecting groups, respectively ... 

The isotherms for the two enantiomers of phenylalanine anilide were measured at 40, 50, 60 and 70 C, and the data fitted to each of the models given in Equations (1-3) [42]. The isotherms obtained by fitting the data to the Langmuir equation were of a quality inferior to the other two. Fittings of the data to the Freundlich and to the bi-Langmuir equations were both good. A comparison of the residuals revealed that the different isotherms of d-PA were best fitted to a bi-Langmuir model, while the... 

Methanol remains the most widely used modifier because it produces highly efficient separations, but it does not always produce the highest selectivity [8]. Recent studies have provided insight into the role of the modifier in enantioselectivity in SFC [69]. Blackwell and Stringham examined a series of phenylalanine analogues on a brush-type CSP and developed a model that allowed prediction of selectivity based on the bulk solvation parameters of various modifiers [70]. Careful choice of modifiers can be used to mask or enhance particular molecular interactions and ultimately provide control of selectivity [71]. 

Figure 30.14 Pathway for the bacterial biosynthesis of phenylalanine from chorismate, involving a Claisen rearrangement.

Selection of these regulatory mutants is often done by using toxic analogues of amino adds for example p-fluoro-DL-phenylalanine is an analogue of phenylalanine. Mutants that have no feedback inhibition or repression to the amino add are also resistant to the analogue amino add. They are therefore selected for and can be used to overproduce the amino add. Some amino add analogues function as false co-repressors, false feedback inhibitors or inhibit the incorporation of foe amino acid into foe protein. 

To achieve overproduction of phenylalanine, the micro-organism should be derepressed at the pheA level and free of inhibition at the arcG level. Both genes are located on the chromosomal DNA of the micro-organism and, by means of amino add analogues such as p-fluoro-DL-phenylalanine, it is possible to make (phenylalanine) feedback resistant mutants of E.cdi (pheA and oroF mutants). The following procedure can be used ... 

---