Stereoelectronic effects on collagen stability: the dichotomy of 4-fluoroproline diastereomers.

@article{Hodges2003StereoelectronicEO,
  title={Stereoelectronic effects on collagen stability: the dichotomy of 4-fluoroproline diastereomers.},
  author={Jonathan A. Hodges and Ronald T. Raines},
  journal={Journal of the American Chemical Society},
  year={2003},
  volume={125 31},
  pages={9262-3}
}
Collagen is the most abundant protein in animals. Natural collagen consists of a triple helix of (Xaa-Yaa-Gly)n chains, in which the Xaa and Yaa residues are often l-proline. Here, a (2S,4S)-4-fluoroproline (flp) residue is shown to be greatly stabilizing in the Xaa position (but destabilizing in the Yaa position). In contrast, a (2S,4R)-4-fluoroproline (Flp) residue is shown to be greatly destabilizing in the Xaa position (but stabilizing in the Yaa position). The dichotomous effect of the… CONTINUE READING

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Eds.Biomedical Frontiers of Fluorine Chemistry

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