𝔖 Bobbio Scriptorium
✦   LIBER   ✦

Solution/solid-phase synthesis of partially modified retro-ψ[NHCH(CF3)]-peptidyl hydroxamates

✍ Scribed by Alessandro Volonterio; Pierfrancesco Bravo; Matteo Zanda

Book ID
104230446
Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
115 KB
Volume
42
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

The synthesis of a novel family of partially-modified (PM) retropeptidyl hydroxamates incorporating a [CH(CF 3 )CH 2 CO] unit as a surrogate of the conventional malonyl group, has been accomplished both in solution and in solid-phase. The key step is the Michael-type N-addition of free or polymer bound a-amino hydroxamates to 3-(E-enoyl)-1,3-oxazolidin-2-ones, which takes place very effectively, although with low stereocontrol. A number of tri-and tetra-peptidyl hydroxamates were obtained either in diastereomerically pure form (by solution-phase synthesis, after chromatographic purification), or as mixtures of two epimers in very good chemical purity (by solid-phase, after release from the resin), demonstrating that this method is suitable for preparing combinatorial libraries of PM retro-[NHCH(CF 3 )]-peptidyl hydroxamates for screening as metalloprotease inhibitors.

📜 SIMILAR VOLUMES

Solid-phase synthesis of partially-modif
Solid-phase synthesis of partially-modified retro and retro-inverso ψ[NHCH(CF3)]-peptides
✍ Alessandro Volonterio; Pierfrancesco Bravo; Nathalie Moussier; Matteo Zanda * 📂 Article 📅 2000 🏛 Elsevier Science 🌐 French ⚖ 193 KB

The solid-phase synthesis of a novel class of retro and retro-inverso peptides featuring a 2[NHCH(CF 3 )] surrogate of the classical (NHÀCO) retro-peptide bond has been accomplished. Wang resin bound a-amino esters 2 were engaged in Michael-type N-additions with 3-(E-enoyl)-1,3-oxazolidin-2one 3, wh

Synthesis, Structure and Conformation of
Synthesis, Structure and Conformation of Partially-Modified Retro- and Retro-Inverso ψ[NHCH(CF3)]Gly Peptides
✍ Alessandro Volonterio; Stefano Bellosta; Fabio Bravin; Maria Cristina Bellucci; 📂 Article 📅 2003 🏛 John Wiley and Sons 🌐 English ⚖ 401 KB

## Abstract Partially modified retro‐ (PMR) and retro‐inverso (PMRI) ψ[NHCH(CF~3~)]Gly peptides, a conceptually new class of peptidomimetics, have been synthesized in wide structural diversity and variable length by aza‐Michael reaction of enantiomerically pure α‐amino esters and peptides with enan