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Issue 28, 2011
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Stereoselective self-sorting in the self-assembly of a Phe–Phe extended guanidiniocarbonyl pyrrole carboxylate zwitterion: formation of two diastereomeric dimers with significantly different stabilities

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Abstract

The ‘dipeptide extended’ guanidiniocarbonyl pyrrole carboxylate zwitterion GCP–Phe–Phe 1 forms stable dimers in DMSO. However, dimerization is highly stereoselective. Only homochiral dimers are formed and the (L,L)·(L,L) dimer (Kdim > 105 M−1) is significantly more stable by a factor of 103 than the diastereomeric (D,L)·(D,L) dimer (Kdim = 120 M−1).

Graphical abstract: Stereoselective self-sorting in the self-assembly of a Phe–Phe extended guanidiniocarbonyl pyrrole carboxylate zwitterion: formation of two diastereomeric dimers with significantly different stabilities

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Publication details

The article was received on 29 Apr 2011, accepted on 31 May 2011 and first published on 13 Jun 2011


Article type: Communication
DOI: 10.1039/C1CC12520F
Chem. Commun., 2011,47, 7953-7955

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    Stereoselective self-sorting in the self-assembly of a Phe–Phe extended guanidiniocarbonyl pyrrole carboxylate zwitterion: formation of two diastereomeric dimers with significantly different stabilities

    F. Rodler, W. Sicking and C. Schmuck, Chem. Commun., 2011, 47, 7953
    DOI: 10.1039/C1CC12520F

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