1186404-59-0Relevant academic research and scientific papers
'backdoor Induction' of chirality: Asymmetric hydrogenation with rhodium(I) complexes of triphenylphosphane-substituted β-turn Mimetics
Kokan, Zoran,Glasovac, Zoran,Majeric Elenkov, Maja,Gredicak, Matija,Jeric, Ivanka,Kirin, Srecko I.
, p. 4005 - 4015 (2014/11/07)
Bioconjugate bidentate ligands 2-10 were obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based β-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodium-catalyzed asymmetric hydrogenation of α,β-unsaturated amino acids. The key feature of the catalysts is the prochiral coordination sphere of the catalytic metal while the chirality is transmitted by 'backdoor induction' from distant hydrogen-bonded amino acids. DFT calculations were applied to study the structure and relative stability of the precatalytic organometallic Rh(I) complexes, with particular emphasis on hydrogen-bonded secondary structures.
Synthesis and evaluation of homodimeric GnRHR antagonists having a rigid bis-propargylated benzene core
Bonger, Kimberly M.,van den Berg, Richard J.B.H.N.,Knijnenburg, Annemiek D.,Heitman, Laura H.,IJzerman, Ad P.,Oosterom, Julia,Timmers, Cornelis M.,Overkleeft, Herman S.,van der Marel, Gijsbert A.
, p. 3744 - 3758 (2008/12/21)
The fact that GPCRs might function in a dimeric fashion is currently well accepted. For GnRHR, a GPCR that regulates gonadotropin release, there is evidence that the receptor also functions as a dimer. We here describe the design and synthesis of a set of dimeric GnRHR antagonists in order to understand the interaction of dimeric ligands to the receptor and to address the question whether GnRHR dimerization is a prerequisite for signalling. Biological evaluation of the compounds shows no discrimination between monomeric and dimeric-ligands in respect to binding affinities, however, the dimeric ligands appear to have different functional properties.
