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Pure Appl. Chem. 75(2-3), 279-292, 2003

Pure and Applied Chemistry

Vol. 75, Issue 2-3

Stereocontrolled construction of conformationally constrained and rigid bis(a-amino acid) derivatives

K. Undheim, J. Efskind, and G. B. Hoven

Department of Chemistry, University of Oslo, N-0315 Oslo, Norway

Abstract: Cystine is regarded as a four-atom bridged bis(a-amino acid). The bridge between the two glycine moieties in cystine has been replaced with all-carbon C4-bridges between the a-carbon of the glycines. The products are dicarba analogs of cystine. Conformational constraints have been conferred on these molecules by insertion of cis- and trans- double bonds in the bridge, by alkylidene substituents, by insertion of a triple bond, by insertion of aromatic or heteroaromatic rings, or otherwise by ring formation. Particularly rigidified dicarba analogs of cystine have been prepared where the a-amino acid carbon is quaternary and part of tricyclic ring structures. Ru(II)-catalyzed ring-closing metathesis (RCM) reactions have been widely used in the preparation of cyclic amino acids. Conformational constraints in acyclic structures result from substitution by simple alkyl, alkenyl, or alkynyl groups at the a-amino acid carbon in the formation of a-quaternary amino acid derivatives.

*Pure Appl.Chem. 75, 141419 (2003). An issue of reviews and research papers based on lectures presented at the 23rd IUPAC International Symposium on the Chemistry of Natural Products, Florence, Italy, 28 July 2 August 2002.

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