Effect of 3-hydroxyproline residues on collagen stability

Journal of the American Chemical Society
C L JenkinsR T Raines

Abstract

Collagen is an integral part of many types of connective tissue in animals, especially skin, bones, cartilage, and basement membranes. A fibrous protein, collagen has a triple-helical structure, which is comprised of strands with a repeating Xaa-Yaa-Gly sequence. l-Proline (Pro) and 4(R)-hydroxy-l-proline (4-Hyp) residues occur most often in the Xaa and Yaa positions. The 4-Hyp residue is known to increase markedly the conformational stability of a collagen triple helix. In natural collagen, a 3(S)-hydroxy-l-proline (3-Hyp) residue occurs in the sequence: 3-Hyp-4-Hyp-Gly. Its effect on collagen stability is unknown. Here, two host-guest peptides containing 3-Hyp are synthesized: (Pro-4-Hyp-Gly)(3)-3-Hyp-4-Hyp-Gly-(Pro-4-Hyp-Gly)(3) (peptide 1) and (Pro-4-Hyp-Gly)(3)-Pro-3-Hyp-Gly-(Pro-4-Hyp-Gly)(3) (peptide 2). The 3-Hyp residues in these two peptides diminish triple-helical stability in comparison to Pro. This destabilization is small when 3-Hyp is in the natural Xaa position (peptide 1). There, the inductive effect of its 3-hydroxyl group diminishes slightly the strength of the interstrand 3-HypC=O.H-NGly hydrogen bond. The destabilization is large when 3-Hyp is in the nonnatural Yaa position (peptide 2). There, its pyrrolidi...Continue Reading

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Citations

Apr 29, 2010·Current Osteoporosis Reports·Roy Morello, Frank Rauch
Aug 5, 2010·Journal of the American Chemical Society·Matthew D ShouldersRonald T Raines
Jun 9, 2009·Chemical Communications : Chem Comm·Colin A ThomasJames G Bann
Jul 16, 2011·The Journal of Biological Chemistry·Russell J FernandesDavid R Eyre
Oct 13, 2012·The Journal of Biological Chemistry·Chenxi YangDaniel S Greenspan
Nov 7, 2013·Acta Crystallographica. Section C, Crystal Structure Communications·P RajalakshmiMohd Mustaqim Rosli
Apr 7, 2009·Annual Review of Biochemistry·Matthew D Shoulders, Ronald T Raines
Jan 28, 2014·PLoS Genetics·Erica P HomanBrendan H L Lee
Mar 6, 2010·Organic & Biomolecular Chemistry·Gregg B Fields
Jan 20, 2015·Molecular Neurobiology·Yu Tang, Weidong Le
Jun 19, 2013·Connective Tissue Research·David M Hudson, David R Eyre
Mar 5, 2010·Critical Reviews in Biochemistry and Molecular Biology·Kelly L Gorres, Ronald T Raines
Sep 12, 2015·Materials Science & Engineering. C, Materials for Biological Applications·Punitha VelmuruganAruna Dhathathreyan
Sep 19, 2008·Genesis : the Journal of Genetics and Development·Terence D CapelliniAnna Di Gregorio
Apr 28, 2006·Protein Science : a Publication of the Protein Society·Ronald T Raines
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