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Amino acid derivatives that stabilize secondary structures of polypeptides—IV. Practical synthesis of 4-alkyamino-3-cyano-azabicyclo[3.2.1.]oct-3-enes (Ben derivatives) as γ-turn templates

✍ Scribed by D.S. Kemp; Jeffrey S. Carter

Book ID: 104227896
Publisher: Elsevier Science
Year: 1987
Tongue: French
Weight: 189 KB
Volume: 28
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)96586-9

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✦ Synopsis

Ben derivatives have been prepared in five steps from 4-hydroxyproline by Barton cyanoethylation, ring closure, and derivitization. Proof of absolute configuration and practical synthesis of pure Ben enantiomers are described.

In the accompanying communication we note that E-enaminonitriles can mimic secondary amides and therefore have promise as building blocks for conformationally restricted analogs of polypeptides. Monocyclic B-enaminonitriles have the disadvantages of partial flexibility and a I CN E Y-Ben-X X

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✍ D.S. Kemp; Jeffrey S. Carter 📂 Article 📅 1987 🏛 Elsevier Science 🌐 French ⚖ 211 KB