Rediscovering Pasteur's Quasiracemates

Wheeler, Kraig A.; Grove, Rebecca C.; Davis, R.; Kassel, W. Scott

doi:10.1002/anie.200704007

Cited by 32 publications

(14 citation statements)

References 12 publications

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“…6a In a quasiracemic pair of molecules, one partner is very similar to the enantiomer of the other. Pasteur first noted that such pairs could co-crystallize (e.g., (+)-bitartrate and (-)-bimalate salts), 9 and the phenomenon has subsequently been documented extensively among small molecules. 9b,10 We were intrigued by the prospect that quasiracemic protein crystallization should provide a sensitive test for the ability of a polypeptide bearing at least one non-canonical subunit to mimic the three-dimensional shape of a prototype containing only canonical residues.…”

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confidence: 99%

Quasiracemic Crystallization as a Tool To Assess the Accommodation of Noncanonical Residues in Nativelike Protein Conformations

et al. 2012

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Quasiracemic crystallization has been used to obtain high-resolution structures of two variants of the villin headpiece subdomain (VHP) that contain a pentafluorophenylalanine (F5Phe) residue in the hydrophobic core. In each case, the crystal contained the variant constructed from L-amino acids and the native sequence constructed from D-amino acids. We were motivated to undertake these studies by reports that racemic proteins crystallize more readily than homochiral forms, and the prospect that quasiracemic crystallization would enable us to determine whether a polypeptide containing a non-canonical residue can closely mimic the tertiary structure of the native sequence. The results suggest that quasiracemic crystallization may prove to be generally useful for assessing mimicry of naturally evolved protein folding patterns by polypeptides that contain unnatural side chain or backbone subunits.

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confidence: 99%

Quasiracemic Crystallization as a Tool To Assess the Accommodation of Noncanonical Residues in Nativelike Protein Conformations

et al. 2012

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“…[23,24] On Cu(110) racemic TA forms a 2D conglomerate of homochiral (1 2, -8 2) and (1 -2, 8 2) domains. [10b] When the TA racemate is mixed with (R)-MA, (S,S)-TA prefers a mixture with (R)-MA which leaves only (R,R)-TA domains to be observed.…”

Section: Close-packing Of Pentagonal Moleculesmentioning

confidence: 99%

Stereochemistry of 2D Molecular Crystallization

Ernst

2014

Chimia

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Different stereochemical aspects of molecular recognition in two-dimensional crystallization on metal surfaces are discussed. Scanning tunneling microscopy, a powerful tool with submolecular resolution capabilities, provides detailed insight into the implications of molecular geometry for the two-dimensional crystal lattice. The examples presented here include a homo- to heterochiral phase transition, tiling with pentagonal molecules, chiral restructuring of a metal surface and diastereomeric recognition between enantiomers of different molecular species via polar forces as well as van der Waals interactions.

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“…Our recent reinvestigation of Pasteur's 1853 quasiracemates (Pasteur, 1853;Wheeler et al, 2008) has motivated us to explore other examples of these unusual materials of historical and supramolecular importance. In 1899, Centnerzwer reported that mixtures of (+)-chlorosuccinic acid and (-)-bromosuccinic acid formed a binary compound that also exhibited quasiracemic behavior (Centnerzwer, 1899).…”

Section: S1 Commentmentioning

confidence: 99%