Alanine analogs

The success of the studies on experimental tumors and of the clinical trials prompted the synthesis of a wide range of Melphalan-related compounds such as the ortho isomer [12—15], the meta isomer [16—20], 3-alanine analogs [19], esters, N-acyl derivatives, and peptides. Despite controversial reports of greater activity or better therapeutical index, none of these analogs replaced Melphalan in clinical use. 

M o o H " V Acyl-sulfonamides Glycine, GABA, and p-alanine analogs Antiatherosclerotics pKj, 4,5 Adrenergic receptor agonist hepatitis C virus Drummond and Johnson Albright et alP Uehling el alP Johansson et alP )... 

Cycloserine, an isoxizolidone, d-alanine analog (250 mg p.o. q. 12 hours), is indicated as an adjunctive treatment in pulmonary or extrapulmonary mberculosis. 

Lee ST, Gardner DR, Chang CW, Panter KE, Molyneux RJ (2008) Separation and measurement of plant alkaloid enantiomers by RP-HPLC analysis of their Fmoc-Alanine analogs. Phytochem Anal 9 395-402... 

This material has an absorption spectrum with maxima at 475, 290 (sh), and 260 nm in H2O. The 475 nm band is characteristic of arylazido-yS-alanine analogs. The concentration of the material is determined from the absorbance at 275 nm by utilizing the molar extinction coefficient, 5.9 X 10 , as previously determined for aryIazido-/3-alanine at 460 nm. ... 

The arylazido- 8-alanine analog has been found to be as well a potent inhibitor of yeast hexokinase and firefly luciferase. ... 

The free amino boronic acid CH3CH(NH2)B(OH)2, an alanine analog, survives for a few hours after its N-silylated-O-isopropyl protected form contacts water. It is an inhibitor of Bacillus stearothermophilus alanine racemase and Salmonella typhimurium D-alanine D-alanine ligase [66]. 

No compound other than the methyl ester of N-benzoyl-Lphenylalanine, 33, is an obvious choice for an open-chain analog of the locked substrate 25 but D-24, on the other hand, may be a locked analog of either N-benzoyl-D-alanine methyl ester 34 or of N-formyl-D-phenylalanine methyl ester 35 (75). If 24 is an analog of 34 rather than 35, the comparison of the two locked analogs made in Section V.B. is not valid the phenyl of 24 would then correspond to the benzoyl phenyl of 34. 

Ribavirin is a guanosine analog synthesized more than 35 years ago, which possesses broad-spectrum antiviral activity against several RNA and DNA viruses in vitro (Sidwell et al. 1972). When administered as monotherapy in patients with chronic hepatitis C, ribavirin induces a decline of serum alanine aminotransferase (ALT) levels while no effect on sustained virologic response is detectable (Di Bisceglie et al. 1992). 

Head-Gordon, T., M. Head-Gordon, M. J. Frisch, C. Brooks HI, and J. A. Pople. 1989. A Theoretical Study of Alanine Dipeptide and Analogs. Int. J. Quantum Chem. Quantum Biol. Symp. 16, 311-322. 

Ai-Stearoylamino acids and their methyl esters were synthesized from enantiomeric and racemic forms of tyrosine, serine, alanine, and tryptophan (Fig. 16). Analogs of these molecules were investigated initially over 30 years ago by Zeelen and Havinga, who found stereochemical differentiation in the monolayer HjA isotherms of these materials (Zeelen, 1956 Zeelen and Havinga, 1958). We have extended this study using more sensitive Langmuir balances, a wider array of dynamic and equilibrium techniques, and the A-stearoyl methyl esters of the amino acids (Harvey et al., 1989 Harvey and Arnett, 1989). 

---