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• W2051552 endingPage "10865" @default.
• W2051552 startingPage "10857" @default.
• W2051552 abstract "Prolyl 4-hydroxylases install a hydroxyl group in the 4R configuration on the γ-carbon atom of certain (2S)-proline (Pro) residues in tropocollagen, elastin, and other proteins to form (2S,4R)-4-hydroxyproline (Hyp). The gauche effect arising from this prevalent post-translational modification enforces a Cγ-exo ring pucker and stabilizes the collagen triple helix. The Hyp diastereomer (2S,4S)-4-hydroxyproline (hyp) has not been observed in a protein, despite the ability of electronegative 4S substituents to enforce the more common Cγ-endo ring pucker of Pro. Here, we use density functional theory, spectroscopy, crystallography, and calorimetry to explore the consequences of hyp incorporation on protein stability using a collagen model system. We find that the 4S-hydroxylation of Pro to form hyp does indeed enforce a Cγ-endo ring pucker but a transannular hydrogen bond between the hydroxyl moiety and the carbonyl of hyp distorts the main-chain torsion angles that typically accompany a Cγ-endo ring pucker. This same transannular hydrogen bond enhances an n→π* interaction that stabilizes the trans conformation of the peptide bond preceding hyp, endowing hyp with the unusual combination of a Cγ-endo ring pucker and high trans/cis ratio. O-Methylation of hyp to form (2S,4S)-4-methoxyproline (mop) eliminates the transannular hydrogen bond and restores a prototypical Cγ-endo pucker. mop residues endow the collagen triple helix with much more conformational stability than do hyp residues. These findings highlight the critical importance of the configuration of the hydroxyl group installed on Cγ of proline residues." @default.
• W2051552 created "2016-06-24" @default.
• W2051552 creator A5007275012 @default.
• W2051552 creator A5019213891 @default.
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• W2051552 creator A5040701048 @default.
• W2051552 creator A5084471611 @default.
• W2051552 date "2010-07-16" @default.
• W2051552 modified "2023-10-16" @default.
• W2051552 title "The Aberrance of the 4<i>S</i> Diastereomer of 4-Hydroxyproline" @default.
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• W2051552 doi "https://doi.org/10.1021/ja103082y" @default.
• W2051552 hasPubMedCentralId "https://www.ncbi.nlm.nih.gov/pmc/articles/2931826" @default.
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• W2051552 hasPublicationYear "2010" @default.
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