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Synthesis 2004(11): 1821-1829  
DOI: 10.1055/s-2004-829131
PAPER
© Georg Thieme Verlag Stuttgart · New York

Hexafluoroacetone as a Protecting and Activating Reagent: Synthesis of New Types of Fluoro-Substituted α-Amino, α-Hydroxy and α-Mercapto Acids

Sergej N. Osipova, Torsten Langeb, Pavel Tsoukerb, Jan Spenglerb, Lothar Hennigb, Beate Kokschb, Stefan Bergerc, Salah M. El-Kousyd, Klaus Burger*b
a A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov str. 18, GSP-1, 117813 Moscow, Russia
b Department of Organic Chemistry, University of Leipzig, Johannisallee 29, 04103 Leipzig, Germany
Fax: +49(341)9736599; e-Mail: burger@organik.chemie.uni-leipzig.de;
c Department of Analytical Chemistry, University of Leipzig, Linnéstrasse 3, 04103 Leipzig, Germany
d Faculty of Science, Minufia University, Shebin El-Kom, Egypt
Further Information

Publication History

Received 7 January 2004
Publication Date:
05 July 2004 (online)

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Abstract

Starting from (S)-aspartic, (S)-malic, (S)-citramalic and (S,R)-thiomalic acid, new types of 4,4-difluoro-substituted α-amino-, α-hydroxy- and α-mercaptopentanoic acids have been synthesized, applying hexafluoroacetone as protecting and activating reagent. The new partially fluorinated α-functionalized carboxylic acids represent interesting monomers for peptide and depsipeptide modification and for rational design and elucidation of secondary structure.

Key words

amino acids - hydroxy acids - mercapto acids - fluorine - peptides

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18

Burger, K.; Radics, G., unpublished results.