50741-47-4Relevant articles and documents
Tandem Tetrahydroisoquinoline-4-carboxylic Acid/β-Alanine as a New Construct Able To Induce a Flexible Turn
Bucci, Raffaella,Bonetti, Andrea,Clerici, Francesca,Contini, Alessandro,Nava, Donatella,Pellegrino, Sara,Tessaro, Davide,Gelmi, Maria Luisa
, p. 10822 - 10831 (2017)
Tetrahydroisoquinoline-4-carboxylic acid, a constrained β2-amino acid named β-TIC, was synthesised for the first time in enantiopure form. The biocatalytic route applied herein represents one of the few successful examples of enzymatic resolution of β2-amino acids. Model tetrapeptides, namely, Fmoc-l-Ala-β-TIC-β-Ala-l-Val-OBn (Fmoc=fluorenylmethyloxycarbonyl, Bn=benzyl), containing both isomers of β-TIC, were prepared. Both computational and NMR spectroscopy studies were performed. A reverse-turn conformation was observed in the case of (R)-β-TIC enantiomer that was obtained in 99 % enantiomeric excess by enzymatic resolution. The β-TIC/β-Ala construct represents the first example of a flexible turn mimetic containing a cyclic and an acyclic β-amino acid. Furthermore, the presence of an aromatic ring of β-TIC could facilitate non-covalent interactions to increase the potential of this scaffold for the preparation of protein–protein interaction modulators.
PALLADIUM CATALYSED SYNTHESIS OF N AND S HETEROCYCLIC ESTERS
Head, Robert A.,Ibbotson, Arthur
, p. 5939 - 5942 (2007/10/02)
Palladium catalysed alkoxycarbonylation of heterocyclic halides affords a simple and versatile synthesis of both N and S heterocyclic esters where a range of catalysts have been studied and a method to employ inexpensive inorganic bases has been found.
