Enantio- and diastereoselective syntheses of cyclic C-alpha-tetrasubstituted alpha-amino acids and their use to induce stable conformations in short peptides

Maity, Prantik and Koenig, Burkhard (2008) Enantio- and diastereoselective syntheses of cyclic C-alpha-tetrasubstituted alpha-amino acids and their use to induce stable conformations in short peptides. BIOPOLYMERS, 90 (1). pp. 8-27. ISSN 0006-3525, 1097-0282

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Abstract

C-alpha-Tetrasubstituted alpha-amino acids are widely used to design and prepare peptides and peptide mimics with constrained conformations. Subcategories of these compounds are cyclic C-alpha-tetrasubstituted alpha-amino acids, in which both alpha-substituents are covalently connected. This survey presents recent advances in the synthesis and application of cyclic C-alpha-tetrasubstituted alpha-amino acids in a systematic order beginning with cyclopropane amino acids, continuing with four, five, six membered rings, and ring structures larger than six-membered. We discuss synthetic routes to the cyclic C-alpha-tetrasubstituted alpha-amino acids and their use as conformation determining elements in peptides. (C) 2007 Wiley Periodicals, Inc.

Item Type: Article
Uncontrolled Keywords: BIOLOGICALLY-ACTIVE PEPTIDES; RING-CLOSING METATHESIS; CHAIN CHIRAL CENTERS; ASYMMETRIC-SYNTHESIS; SIDE-CHAIN; ETHYLENE BIOSYNTHESIS; ORGANIC-SYNTHESIS; ALPHA,ALPHA-DIALKYL-ALPHA-AMINO ACIDS; 1-AMINOCYCLOPROPANE-1-CARBOXYLIC ACID; C-ALPHA,ALPHA-DIALKYLATED GLYCINES; artificial amino acids; cyclic compounds; synthesis; conformation
Subjects: 500 Science > 540 Chemistry & allied sciences
Divisions: Chemistry and Pharmacy > Institut für Organische Chemie > Lehrstuhl Prof. Dr. Burkhard König
Depositing User: Petra Gürster
Date Deposited: 18 Dec 2020 09:40
Last Modified: 18 Dec 2020 09:40
URI: https://pred.uni-regensburg.de/id/eprint/31562

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