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Solid-phase synthesis of partially-modified retro and retro-inverso ψ[NHCH(CF3)]-peptides

✍ Scribed by Alessandro Volonterio; Pierfrancesco Bravo; Nathalie Moussier; Matteo Zanda *

Book ID
104210664
Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
193 KB
Volume
41
Category
Article
ISSN
0040-4039

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✦ Synopsis

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, which took place very eectively. Highly chemoselective exocyclic oxazolidinone cleavage, followed by parallel couplings of the resulting polymer bound pseudo-peptides 6 with further a-amino esters, and ®nal release from the resins 7 delivered a library of nine 2[NHCH(CF 3 )] retro and retro-inverso pseudo-tripeptides 8 with purity ranging from 75 to>95%.

📜 SIMILAR VOLUMES

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

Solution/solid-phase synthesis of partia
Solution/solid-phase synthesis of partially modified retro-ψ[NHCH(CF3)]-peptidyl hydroxamates
✍ Alessandro Volonterio; Pierfrancesco Bravo; Matteo Zanda 📂 Article 📅 2001 🏛 Elsevier Science 🌐 French ⚖ 115 KB

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 bo