106407-83-4Relevant articles and documents
Synthetic macrocyclic peptidomimetics as tunable pH probes for the fluorescence imaging of acidic organelles in live cells
Galindo, Francisco,Burguete, M. Isabel,Vigara, Laura,Luis, Santiago V.,Kabir, Nurul,Gavrilovic, Jelena,Russell, David A.
, p. 6504 - 6508 (2005)
(Chemical Equation Presented) Acid test: Macrocyclic compounds that comprise a 9,10-anthracene subunit linked by a C2-symmetric peptidomimetic chain (see formula) are useful as fluorescent probes in a pH range of biomedical interest. Changes in
Coordination of Cu2+ Ions to C 2 Symmetric pseudopeptides derived from valine
Blasco, Salvador,Burguete, M. Isabel,Clares, M. Paz,Garcia-Espana, Enrique,Escorihuela, Jorge,Luis, Santiago V.
scheme or table, p. 7841 - 7852 (2010/11/16)
The acid-base and coordination properties of a family of pseudopeptidic ligands with C2 symmetry derived from valine (4a-e) have been studied using a variety of techniques as a model for metal coordination in peptides and proteins. The Cu2+ cation has been selected for coordination studies, although, for comparison, some results for Zn2+ are also presented. Good agreement has been obtained between the results obtained by potentiometric titrations, spectroscopic analysis, and mass spectrometry (ESI) studies. These results highlight the potential for the use of ESI MS for characterizing the nature of the complex species formed. Clearly, the Cu 2+ complexes are much more stable than the Zn2+ complexes. While the role of the aliphatic spacer seems to be very minor in the case of the Zn2+ complexes, revealing the ability of this cation to accommodate different coordination environments, this role is critical in the case of Cu2+. Different complexes with 1:1 or 2:2 Cu2+:L stoichiometries can be formed according to the length of the spacer and the basicity of the media. This is fully illustrated by the resolution of the X-ray structures of two different Cu2+ complexes corresponding to the ligands containing a spacer with two methylene groups (ligand 4a, complex 6a [Cu2(H-1L)2](ClO4)2 with a 2:2 stoichiometry) and a propylene spacer (4b, complex 5b [CuH-2L] CH3CH2OH with a 1:1 stoichiometry).
Efficient macrocyclization of U-turn preorganized peptidomimetics: The role of intramolecular H-bond and solvophobic effects
Becerril, Jorge,Bolte, Michael,Burguete, M. Isabel,Galindo, Francisco,Garcia-Espana, Enrique,Luis, Santiago V.,Miravet, Juan F.
, p. 6677 - 6686 (2007/10/03)
Simple peptidomimetic molecules derived from amino acids were reacted with meta- and parabis(bromomethyl) benzene in acetonitrile to very efficiently yield macrocyclic structures. The cyclization reaction does not require high dilution techniques and seems to be insensitive to the size of the formed macrocycle. The analysis of data obtained by 1H NMR, single-crystal X-ray diffraction, fluorescence measurements, and molecular mechanics indicate that folded conformations can preorganize the system for an efficient cyclization. The role played by intramolecular hydrogen-bonding and solvophobic effects in the presence of folded conformations is analyzed.