312311-58-3Relevant academic research and scientific papers
Lipase-involved strategy to the enantiomers of 4-benzyl-β-lactam as a key intermediate in the preparation of β-phenylalanine derivatives
Li, Xiang-Guo,Kanerva, Liisa T.
, p. 197 - 205 (2007/10/03)
A simple chemoenzymatic method for the preparation of the enantiomers of 4-benzyl-β-lactam (4-benzylazetidin-2-one) from allylbenzene has been described. The enantiomers of this key intermediate have been used to produce the corresponding enantiomers of β-phenylalanine and N-Boc-protected β-phenylalanine amide through the simple cleavage of the lactam ring by acid-catalyzed hydrolysis and by ammonolysis, respectively. Burkholderia cepacia lipase-catalyzed kinetic double resolution techniques were responsible for achieving enantiopurity in the products. This was performed through the acylation of N-hydroxymethylated β-lactam followed by the butanolysis of the obtained (S)-ester. Direct lipase-catalyzed cleavage of the β-lactam ring has also been studied.
Endomorphin-1 analogues containing β-proline are μ-opioid receptor agonists and display enhanced enzymatic hydrolysis resistance
Cardillo, Giuliana,Gentilucci, Luca,Qasem, Ahmed R.,Sgarzi, Fabio,Spampinato, Santi
, p. 2571 - 2578 (2007/10/03)
In this paper we describe the synthesis and affinity toward the μ-opioid receptor of some tetrapeptides obtained from endomorphin-1, H-Tyr-Pro-Trp-Phe-NH2 (1), by substituting each amino acid in turn with its homologue. The ability to bind μ -opioid receptors depends on the β-amino acid, and in particular 4, which contains β-L-Pro, has a KI, in the nanomolar range. The peptides 4 and 5 are significantly more resistant to enzymatic hydrolysis than 1. The same compounds, as well as the μ-opioid receptor agonist DAMGO, produced a concentration-dependent inhibition of forskolin-stimulated cyclic AMP formation, thus behaving as μ-opioid agonists. These features suggest that this novel class of endomorphin-1 analogues may represent suitable candidates for the in vivo investigation as potential μ-opioid receptor agonists.
Pseudoaxially disubstituted cyclo-β3-tetrapeptide scaffolds
Sutton, Peter W.,Bradley, Adrian,Farràs, Jaume,Romea, Pedro,Urpí, Fèlix,Vilarrasa, Jaume
, p. 7947 - 7958 (2007/10/03)
An N,N-disubstituted cyclo-β3-tetrapeptide, identified as a potential molecular scaffold, has been synthesised on a multigram scale from β-homophenylalanine by employing a nosylate-based protection strategy. C2-Symmetric derivatives containing pseudoaxial, combinatorially addressable functionalities have been prepared from the parent cyclopeptide. (C) 2000 Elsevier Science Ltd.
