209252-15-3Relevant articles and documents
Solid phase synthesis of novel α/β-tetrapeptides, electrospray ionization mass spectrometric evaluation of their metal cation complexation behavior, and conformational analysis using density functional theory (DFT)
Bandala, Yamir,Avina, Judit,Gonzalez, Tania,Rivero, Ignacio A.,Juaristi, Eusebio
, p. 349 - 358 (2008/12/20)
Thirty-four novel α/β-tetrapeptides (1-34) have been prepared employing solid-phase and in-parallel synthetic protocols. α/β- Tetrapeptides 1-34 were prepared by a combination of three α-amino acid residues (alanine (Ala), phenylalanine (Phe), and isoleucine (Ile)) with one β-amino acid residue (β3-homophenylglycine). The corresponding complexes of several selected α/β-tetrapeptides with alkali, alkaline earth, and transition metals, [tP + M+], were evaluated using ion electrospray-ionization mass spectrometry (ESI-MS). According to the results from analysis of mixtures, we can conclude that the position of the β-amino acid is determinant in the affinity toward different metal cations. Computational modeling (DFT, B3LYP 6-311++G) provided useful information regarding the most likely coordination sites of the metal ions on the receptor α/β-tetrapeptide 12, HO2C-α- Phe-α-Phe-α-Ile-β3-hPhg-NH2, as well as the conformational changes induced by the metal upon [tP + M+] complex formation. Copyright
Synthesis of Fmoc-β-homoamino acids by ultrasound-promoted wolff rearrangement
Müller, Annett,Vogt, Carla,Sewald, Norbert
, p. 837 - 841 (2007/10/03)
A highly efficient protocol for Amdt-Eistert chain elongation of the base-labile fluorenylmethoxycarbonyl (Fmoc) protected α-amino acids by Ag+- catalyzed, ultrasound-promoted Wolff rearrangement of the corresponding α- diazo ketones at room temperature is described. The enantiomeric purity of the products was examined by capillary zone electrophoresis with chiral buffer systems.
