31795-93-4Relevant articles and documents
Conformational analysis and mu-opioid receptor affinity of short peptides, endomorphin models in a low polarity solvent.
Cardillo, Giuliana,Gentilucci, Luca,Tolomelli, Alessandra,Qasem, Ahmed R,Spampinato, Santi,Calienni, Maria
, p. 3010 - 3014 (2003)
Peptide carbamates containing the sequence H-Pro-Trp-PheNH2 showed in CDCl3 restricted conformations stabilized by the presence of a gamma-turn. To test the reliability of the peptides as endomorphin conformational models, we measured the affinities for mu-receptors labelled with [3H]-DAMGO. In particular, Cbz-Pro-Trp-PheNH2 displayed a nanomolar affinity.
Improved synthesis of proline-derived Ni(II) complexes of glycine: Versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids
Ueki, Hisanori,Ellis, Trevor K.,Martin, Collin H.,Boettiger, Tomas U.,Bolene, Shawna B.,Soloshonok, Vadim A.
, p. 7104 - 7107 (2003)
A synthetically practical and operationally convenient method for preparing (S)-2-[N-(N′-benzylprolyl)-amino]benzophenone (BPBP) and hitherto unknown (S)-2-[N-(N′-benzylprolyl)amino]-4-methylbenzophenone (4-Me-BPBP), (S)-2-[N-(N′-benzylprolyl)amino]-5-nitrobenzophenone (5-NO2-BPBP), and their corresponding Ni(II) complexes with glycine [GlyNi(II)BPBP], a widely used chiral equivalent of nucleophilic glycine, and new analogues [GlyNi(II)-4-Me-BPBP] and [GlyNi(II)-5-NO2-BPBP] is described. The key step of the method is the synthetically efficient amid bond formation between the corresponding o-aminobenzophenones, featuring significant steric shielding and low nucleophilicity of the amino functionality as well as sterically constrained (S)-N-benzylproline (BP).
Preparation of labeled aromatic amino acids: Via late-stage18F-fluorination of chiral nickel and copper complexes
Craig, Austin,Kolks, Niklas,Urusova, Elizaveta A.,Zischler, Johannes,Brugger, Melanie,Endepols, Heike,Neumaier, Bernd,Zlatopolskiy, Boris D.
supporting information, p. 9505 - 9508 (2020/09/03)
A general protocol for the preparation of 18F-labeled AAAs and α-methyl-AAAs applying alcohol-enhanced Cu-mediated radiofluorination of Bpin-substituted chiral complexes using Ni/Cu-BPX templates as double protecting groups is reported. The chiral auxiliaries are easily accessible from commercially available starting materials in a few synthetic steps. The versatility of the method was demonstrated by the high-yielding preparation of a series of [18F]F-AAAs and the successful implementation of the protocol into automated radiosynthesis modules. This journal is
Catalytic Transfer Hydrodebenzylation with Low Palladium Loading
Yakukhnov, Sergey A.,Ananikov, Valentine P.
supporting information, p. 4781 - 4789 (2019/09/16)
A highly-efficient catalytic system for hydrodebenzylation reaction is described. The cleavage of O-benzyl and N-benzyl protecting groups was performed using an uncommonly low palladium loading (0.02–0.3 mol%; TON up to 5000) in a relatively short reaction time. The approach was used for a variety of substrates including pharmaceutically important precursors, and gram-scale deprotection reaction was shown. Transfer conditions together with easy-to-make Pd/C catalyst are the key features of this debenzylation scheme. (Figure presented.).