A short synthesis of 4-amino-3-hydroxybutyric acid (GABOB) via allyl cyanide

4-Amino-3-hydroxybutyric acid was synthesized from allyl cyanide in four steps in an overall yield of 38%. Ultrasonically promoted epoxidation of allyl cyanide with m-chloroperoxybenzoic acid giving oxiranylacetonitrile was used as a key step.     

Ein einfacher Zugang zu (R)-γ-Amino-β-hydroxybuttersäure (GABOB) aus natürlichem (2S, 4R)-4-Hydroxyprolin

The oxidative decarboxylation sequence (1a 2a 3a 4a 5a) affording -aminobutanoic acid (5a) is adapted to the synthesis of its hydroxy derivative5b. A facile high yield conversion of (2S, 4R)-4-hydroxyproline-methylester-hydrochloride (7) to (R)-GABOB (5b) on a preparative scale is reported with the hydroxypyrrolidone8 as the intermediate.

     

Fluorinated peptidomimetics: synthesis, conformational and biological features

Peptides modified with fluoroalkyl functions in key backbone positions have been scarcely studied so far. Thus, little is known about their synthesis, their structural and physico-chemical properties, and their biological features. Our interest in this field of research led to the development of stereocontrolled synthetic protocols, both in solution and in solid phase, for many different fluoroalkyl peptidomimetics, some of which are overviewed in this paper: (a) ψ[CH(CF₃)NH]-peptide mimics holding a great potential as hybrids between natural peptides and hydrolytic transition state analogs; (b) trifluoromethyl (Tfm) malic peptidomimetics as micromolar inhibitors of some matrix metalloproteinases; (c) bis-Tfm analogs of Pepstatin A, that are nanomolar and selective inhibitors of the protozoal aspartyl protease Plasmepsin II.