Phenylalanine structure

Kamm, W., Hauptmann, J., Behrens, I., Sturzebecher, J., Dullweber, F., Gohlke, H., Stubbs, M., Klebe, G., Kissel, T., Transport of peptido-mimetic thrombin inhibitors with a 3-amidino-phenylalanine structure permeability and efflux mechanism in monolayers of a human intestinal cell line (Caco-2), Pharm. Res. 2001, 18, 1110-1118. 

Because of the similarity of the active sites of renin and HIV protease, the approach used was one that had been developed for renin inhibitors. HIV protease cleaves the linkage between two amino acids — phenylalanine (Structure 4.3) and proline (Structure 4.4). 

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

Figure 2-32. Structure diagrams of a) phenylalanine and b) 1-isopropyladamantane c), d) different representations of 1 f ,4S,4aS,6fi,SaS-octahydro-4,8a,9,9-tetraiTiethyl-l, 6-methano-iiaphthalen-1 (2H -ol.

Figure 2 40. To illustrate the isomorphism problem, phenylalanine is simplified to a core without representing the substituents. Then every core atom is numbered arbitrarily (first line). On this basis, the substituents of the molecule can be permuted without changing the constitution (second line). Each permutation can be represented through a permutation group (third line). Thus the first line of the mapping characterizes the numbering of the atoms before changing the numbering, and the second line characterizes the numbering afterwards. In the initial structure (/) the two lines are identical. Then, for example, the substituent number 6 takes the place of substituent number 4 in the second permutation (P2), when compared with the reference molecule.

Figure 2-62. The substituted phenyl derivative is an example of a typical Markush structure. Herein, a number of compounds are described in one structure diagram by fill-ins. Phenylalanine is one of these structures when r is COOH, is H, and X is H.

D, J Sturzebecher and WBode 1991. Geometry of Binding of the N-Alpha-Tosylated Piperidides of weffl-Amidino-Phenylalanine, Para Amidino-Phenylalanine and para-Guanidino-Phenylalanine to Thrombin and Trypsin - X-ray Crystal Structures of Their Trypsin Complexes and Modeling of their Thrombin Complexes. FEBS Letters 287 133-138. 

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... 

Page 1176 (Figure 28 11) is adapted from crystallographic coordinates deposited with the Protein Data Bank PDB ID 6TNA Sussman J L Holbrook S R Warrant R W Church G M Kim S H Crystal Structure of Yeast Phenylalanine tRNA I Crystallographic Refinement / Mol Biol 1978 126 607 (1978)... 

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). 

The nonpolar amino acids (Figure 4.3a) include all those with alkyl chain R groups (alanine, valine, leucine, and isoleucine), as well as proline (with its unusual cyclic structure), methionine (one of the two sulfur-containing amino acids), and two aromatic amino acids, phenylalanine and tryptophan. Tryptophan is sometimes considered a borderline member of this group because it can interact favorably with water via the N-H moiety of the indole ring. Proline, strictly speaking, is not an amino acid but rather an a-imino acid. 

The Henry reactions of A, ALdibenzyl-L-phenylalaninal with nitroalkanes using 1.2 equiv of tetrabutylammonium fluoride (TBAF) as the catalyst proceed in ahighly stereoselective manner, as shown in Eqs. 3.82 and 3.83. This reaction provides rapid and stereoselective access to important molecules containing 1,3-diamino-2-hydroxypropyl segments, which are cenhal structural subunit of the HIV protease inhibitor amprenavir (in Scheme 3.21). 

Therapeutic Function Cancer chemotherapy Chemical Name 4-[bis(2-chloroethyl)amino]-L-phenylalanine Common Name Alanine nitrogen mustard L-sarcolysine Structural Formula... 

An interesting aspect of the benzofuran cationic polymerization was uncovered by Natta, Farina, Peraldo and Bressan who reported in 196160,61 that an asymmetric synthesis of an optically active poly(benzofuran) could be achieved by using AlCl2Et coupled with (-)j3-phenylalanine, (+)camphorsulphonic acid or with (-)brucine. The optical activity was definitely due to the asymmetric carbon atoms in the polymer chain, indicating that at least some of the polymer s macromolecules possessed a di-isotactic structure, v/ z.62 ... 

---