Literature DB >> 17152925

Convenient and efficient syntheses of 4-hydroxy-2(E)-nonenal and 4-oxo-2(E)-nonenal.

Reshma F Kurangi1, Santosh G Tilve, Ian A Blair.   

Abstract

Lipid peroxidation products 4-hydroxy-2(E)-nonenal (HNE) and 4-oxo-2(E)-nonenal (ONE) were conveniently synthesized using Wittig and Horner-Wardsworth-Emmons (HWE) reaction. Wittig or HWE reaction between an easily prepared phosphorane or phosphonate with glyoxal dimethyl acetal gave a protected 4-oxo-2(E)-nonenal. Hydrolysis gave 4-oxo-2(E)-nonenal, whereas reduction followed by hydrolysis gave 4-hydroxy-2(E)-nonenal.

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Year:  2006        PMID： 17152925     DOI： 10.1007/s11745-006-5043-4

Source DB:  PubMed          Journal:  Lipids        ISSN： 0024-4201            Impact factor:   1.646


  25 in total

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Authors:  A L Gard; V G Solodushko; G Waeg; T Majic
Journal:  Microsc Res Tech       Date:  2001-03-15       Impact factor: 2.769

2.  A synthesis of 4-hydroxy-2-trans-nonenal and 4-(3H) 4-hydroxy-2-trans-nonenal.

Authors:  A Chandra; S K Srivastava
Journal:  Lipids       Date:  1997-07       Impact factor: 1.880

3.  Histochemical detection of 4-hydroxynonenal protein in Alzheimer amyloid.

Authors:  Y Ando; T Brännström; K Uchida; N Nyhlin; B Näsman; O Suhr; T Yamashita; T Olsson; M El Salhy; M Uchino; M Ando
Journal:  J Neurol Sci       Date:  1998-04-01       Impact factor: 3.181

4.  Crosslinking of apolipoprotein E by products of lipid peroxidation.

Authors:  T J Montine; D Y Huang; W M Valentine; V Amarnath; A Saunders; K H Weisgraber; D G Graham; W J Strittmatter
Journal:  J Neuropathol Exp Neurol       Date:  1996-02       Impact factor: 3.685

5.  Hydroxynonenal adducts indicate a role for lipid peroxidation in neocortical and brainstem Lewy bodies in humans.

Authors:  Rudy J Castellani; George Perry; Sandra L Siedlak; Akihiko Nunomura; Shun Shimohama; Jing Zhang; Thomas Montine; Lawrence M Sayre; Mark A Smith
Journal:  Neurosci Lett       Date:  2002-02-08       Impact factor: 3.046

Review 6.  Oxidative stress in Parkinson's disease.

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Journal:  Ann Neurol       Date:  2003       Impact factor: 10.422

7.  Covalent modifications to 2'-deoxyguanosine by 4-oxo-2-nonenal, a novel product of lipid peroxidation.

Authors:  D Rindgen; M Nakajima; S Wehrli; K Xu; I A Blair
Journal:  Chem Res Toxicol       Date:  1999-12       Impact factor: 3.739

Review 8.  Cytotoxicity and genotoxicity of lipid-oxidation products.

Authors:  H Esterbauer
Journal:  Am J Clin Nutr       Date:  1993-05       Impact factor: 7.045

9.  E-4-hydroxy-2-nonenal is cytotoxic and cross-links cytoskeletal proteins in P19 neuroglial cultures.

Authors:  T J Montine; V Amarnath; M E Martin; W J Strittmatter; D G Graham
Journal:  Am J Pathol       Date:  1996-01       Impact factor: 4.307

10.  Immunohistochemical detection of 4-hydroxynonenal protein adducts in Parkinson disease.

Authors:  A Yoritaka; N Hattori; K Uchida; M Tanaka; E R Stadtman; Y Mizuno
Journal:  Proc Natl Acad Sci U S A       Date:  1996-04-02       Impact factor: 11.205
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  3 in total

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Journal:  J Labelled Comp Radiopharm       Date:  2011-05-15       Impact factor: 1.921

2.  A role for the p75 neurotrophin receptor in axonal degeneration and apoptosis induced by oxidative stress.

Authors:  Bradley R Kraemer; John P Snow; Peter Vollbrecht; Amrita Pathak; William M Valentine; Ariel Y Deutch; Bruce D Carter
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3.  Structure-activity analysis of diffusible lipid electrophiles associated with phospholipid peroxidation: 4-hydroxynonenal and 4-oxononenal analogues.

Authors:  Colleen E McGrath; Keri A Tallman; Ned A Porter; Lawrence J Marnett
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  3 in total

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