Communication

Conformational Properties of 4-Mercaptoproline and Related Derivatives†

  1. Sergio A. Cadamuro Dr.1,
  2. Rudolf Reichold2,
  3. Ulrike Kusebauch Dr.1,
  4. Hans-Jürgen Musiol1,
  5. Christian Renner Priv.-Doz. Dr.1,3,
  6. Paul Tavan Prof. Dr.2,
  7. Luis Moroder Prof. Dr.1

Article first published online: 28 JAN 2008

DOI: 10.1002/anie.200704310

Issue

Angewandte Chemie International Edition

Angewandte Chemie International Edition

Volume 47, Issue 11, pages 2143–2146, February 28, 2008

Additional Information

How to Cite

Cadamuro, Sergio A., Reichold, R., Kusebauch, U., Musiol, H.-J., Renner, C., Tavan, P. and Moroder, L. (2008), Conformational Properties of 4-Mercaptoproline and Related Derivatives. Angew. Chem. Int. Ed., 47: 2143–2146. doi: 10.1002/anie.200704310

Author Information

  1. 1

    Max-Planck-Institut für Biochemie, Am Klopferspitz 18, 82152 Martinsried, Germany, Fax: (+49) 89-8578-2847 http://www.biochem.mpg.de/en/rg/moroder/

  2. 2

    Lehrstuhl für Biomolekulare Optik, Ludwig-Maximilians-Universität, Oettingenstrasse 67, 80538 München, Germany

  3. 3

    Current address: Deutsche Forschungsgemeinschaft, Kennedyallee 40, 53170 Bonn/Bad-Godesberg, Germany

  1. †

    This work was supported by the Deutsche Forschungsgemeinschaft (SFB 533, A8, and C3).

Publication History

  1. Issue published online: 22 FEB 2008
  2. Article first published online: 28 JAN 2008
  3. Manuscript Received: 18 SEP 2007

Funded by

  • Deutsche Forschungsgemeinschaft

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Keywords:

  • conformation analysis;
  • peptides;
  • proline;
  • pyrrolidine;
  • stereoelectronic effects
Thumbnail image of graphical abstract

Spot the difference: Conformational analysis of the 2S,4R and 2S,4S epimers of N-acetyl-4-mercaptopyrrolidine-2-carboxylic acid methyl esters reveals ring-pucker preferences that are opposite of those of the hydroxyproline derivatives (see scheme). Replacement of proline or hydroxyproline in polypeptides with the chalcogen analogue should allow for fine-tuning of the complex interplay of noncovalent interactions, steric hindrance, and stereoelectronic effects.

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