𝔖 Bobbio Scriptorium
✦   LIBER   ✦

A new synthesis of α-amino acids (E)-β,γ-enol ethers

✍ Scribed by M. Daumas; L. Vo-quang; Y. Vo-quang; F. Le Goffic

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
259 KB
Volume
30
Category
Article
ISSN
0040-4039

No coin nor oath required. For personal study only.

✦ Synopsis

Various N-protected amino acids bearing an enol ether side chain were synthesized by a new method allowing a great versatility in the introduction of both the N-protective groups and the enol ether moieties. This method deals with a Wittig-Homer condensation to afford the a$-dehydro homoserine ethers derivatives, followed by a regio and stereo selective isomerization into P,y-enol ethers.

Dehydro-amino acids as well as dehydro peptides have received much attention in recent literature (1). As potent enzyme inhibitors or naturally occurring antimetabolites (2), they are targets of choice in the rational design of new drugs.

Among them, P,y-unsaturated amino acids 1 or 2 have been shown to irreversibly inhibit PLP dependent enzymes (3) and a "suicide substrate" mechanism of action has been postulated (3ab, 4 ).

📜 SIMILAR VOLUMES

Non-proteinogenic amino acid synthesis:
Non-proteinogenic amino acid synthesis: Synthesis of β,γ-unsaturated α-amino acids from asparic acid
✍ Jack E Baldwin; Mark G Moloney; Michael North 📂 Article 📅 1989 🏛 Elsevier Science 🌐 French ⚖ 609 KB

A general, stereospecific, synthesis of S,Y-unsaturated a-amino acids using the S-anion derived from aspartic acid is described . S,Y-Unsaturated amino acids have been found to be reversible or irreversible inhibitors of a number of enzymes,' and this has prompted a number of racemic syntheses of th