PMID: 9164839May 15, 1997Paper

Structural characterization of the products of hydroxyl-radical damage to leucine and their detection on proteins

The Biochemical Journal
S L Fu, Roger T Dean

Abstract

We have previously reported the formation of valine hydroperoxides and aldehydes from hydroxyl-radical attack on free valine and protein molecules. We have also demonstrated that the major degradation products of valine hydroperoxides by several biochemical and cellular systems are the corresponding hydroxides, and therefore proposed that hydroxyvalines may serve as useful in vivo markers for studying protein oxidation. Here we have undertaken the structural elucidation of the oxidation products of leucine, another amino acid which is very susceptible to peroxidation. Hydroxyl-radical (HO.) attack on l-leucine in the presence of oxygen, followed by NaBH4 reduction, gave rise to five major oxidation products which have been isolated and identified. On the basis of chemical and spectroscopic evidence, the five products have been identified as (2S)-gamma-hydroxyleucine, (2S,4S)-delta-hydroxyleucine, (2S,4R)-delta-hydroxyleucine, (2S,4R)-4-methylproline (trans-4-methyl-l-proline) and (2S,4S)-4-methylproline (cis-4-methyl-l-proline). The three hydroxyleucines have been confirmed to be the reduction products of the corresponding hydroperoxyleucines, while the two proline analogues are from reduction of their corresponding cyclic Schi...Continue Reading

Citations

Sep 3, 2010·Journal of the Science of Food and Agriculture·Karin J Larsson, Ingrid K Undeland
Sep 10, 2014·Annual Review of Genetics·Tammy BullwinkleMichael Ibba
Sep 23, 2018·Protein Science : a Publication of the Protein Society·Jimin WangPeter B Moore
Sep 24, 2004·Journal of Biomedical Materials Research. Part B, Applied Biomaterials·Michael DiCiccoSusan A Jansen-Varnum
Nov 2, 2005·Redox Report : Communications in Free Radical Research·Gregorio Martínez-SánchezOlga Sonia León-Fernández
Jan 30, 2009·Journal of Clinical Biochemistry and Nutrition·Shoichi EzakiMasanori Tamura
Apr 21, 2010·International Journal of Developmental Neuroscience : the Official Journal of the International Society for Developmental Neuroscience·Preeticia Dkhar, Ramesh Sharma
Mar 31, 2016·The Biochemical Journal·Michael J Davies
Mar 29, 2019·Angewandte Chemie·Michael Hellwig
Oct 24, 1998·The Journal of Biological Chemistry·S FuR Truscott
Sep 16, 2010·The Biochemical Journal·Alexander V PeskinChristine C Winterbourn
Dec 2, 2008·Neurological Research·Prem KumarAnjali Rao
Apr 25, 2013·Molecular and Cellular Biochemistry·Preeticia Dkhar, Ramesh Sharma
Dec 19, 2006·Nature Chemical Biology·Alexandre AmbrogellyDieter Söll
Nov 27, 2009·European Journal of Mass Spectrometry·Ana ReisPedro Domingues
Jun 22, 2013·American Journal of Epidemiology·Yan ZhengJennifer A Nettleton
Jul 25, 2008·Biomedical Chromatography : BMC·Conceição FonsecaM Rosário M Domingues
Apr 14, 2016·Protein Science : a Publication of the Protein Society·Jimin Wang
Dec 3, 2020·Frontiers in Molecular Biosciences·Frances M Smith, Daniel J Kosman
Feb 6, 2020·International Journal of Biological Macromolecules·Zarina ArifKhursheed Alam
Sep 26, 2007·Chemical Research in Toxicology·Elena S DreminaChristian Schöneich
Mar 21, 1998·Archives of Biochemistry and Biophysics·J A SilvesterM J Davies
Jan 21, 2000·Free Radical Biology & Medicine·M J DaviesR T Dean
Apr 9, 2002·Free Radical Biology & Medicine·Kenneth J RodgersRoger T Dean
Mar 14, 2001·Biochimica Et Biophysica Acta·C L Hawkins, M J Davies
May 29, 2002·Chemistry & Biology·Brenda ValderramaRafael Vazquez-Duhalt
Nov 27, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Yu YamaguchiJun Haginaka
Nov 27, 2002·Journal of Chromatography. B, Analytical Technologies in the Biomedical and Life Sciences·Fu-Chou ChengTung-Hu Tsai
Dec 25, 2002·Free Radical Biology & Medicine·Henrietta A Headlam, Michael J Davies
Apr 11, 2003·Journal of the American Society for Mass Spectrometry·M Rosário M DominguesAntónio J V Ferrer-Correia
Apr 15, 2004·Free Radical Biology & Medicine·Henrietta A Headlam, Michael J Davies
Sep 29, 2004·Free Radical Biology & Medicine·Benedicta N NukunaVernon E Anderson
Feb 1, 2005·Biochimica Et Biophysica Acta·Michael J Davies
Apr 25, 2006·Free Radical Biology & Medicine·Henrietta A HeadlamMichael J Davies

❮ Previous
Next ❯

Related Concepts

Related Feeds

ApoE, Lipids & Cholesterol

Serum cholesterol, triglycerides, apolipoprotein B (APOB)-containing lipoproteins (very low-density lipoprotein (VLDL), immediate-density lipoprotein (IDL), and low-density lipoprotein (LDL), lipoprotein A (LPA)) and the total cholesterol/high-density lipoprotein (HDL) cholesterol ratio are all connected in diseases. Here is the latest research.