Practical highly enantioselective synthesis of (R)- and (S)-(E)-4-hydroxynon-2-enal

Acta Biochimica Polonica

Volumn 56, Issue 1, 2009, Pages 189-193

  Komisarski, Marek ^a   Kaczmarska, Zuzanna ^a,b   Kuśmierek, Jarosław T ^a  

^a INSTITUTE OF BIOCHEMISTRY AND BIOPHYSICS   (Poland)

^b UNIVERSITY OF WARSAW   (Poland)

Author keywords

(E) 4 hydroxynon 2 enal (4 HNE) synthesis; 4 HNE enantiomers; Asymmetric synthesis; Candida antarctica lipase; Lipid peroxidation

Indexed keywords

CANDIDA ANTARCTICA;

EID: 67249088363     PISSN: 0001527X     EISSN: 1734154X     Source Type: Journal    
DOI: 10.18388/abp.2009_2532     Document Type: Article

References (21)

1. Allevi P, Anastasia M, Cajone F, Ciuffreda P, Sanvito AM (1993) Enzymatic resolution of (R)- and (S)-(E)-4-hydroxyalk-2-enals related to lipid peroxidation. J Org Chem 58: 5000-5002.
2. 2+ dependent. Chem Res Toxicol 20: 887-895.
3. Bringmann G, Gassen M, Schneider S (1994a) Toxic aldehydes formed by lipid peroxidation. I. Sensitive, gas chromatography-based stereoanalysis of 4-hydroxy-alkenal, toxic products of lipid peroxidation. J Chromatog A 670: 153-160.
4. Bringmann G, Gassen M, Lardy R (1994b) 4-Hydroxynon-2-enal, a cytotoxic lipid peroxidation product, and its C5 analog 4-hydroxypent-2-enal: enantioselective synthesis and stereoanalysis. Tetrahedron 50: 10245-10252.
5. 3H) 4-hydroxy-2-trans-nonenal. Lipids 32: 779-782.
6. Chojnacka A, Obara R, Wawrzenczyk C (2007) Kinetic resolution of racemic secondary aliphatic allylic alcohols in lipase catalyzed transesterification. Tetrahedron: Asymmetry 18: 101-107.
7. 2-propanodeoxyguanosine adducts as endogenous DNA lesions in rodents and humans. In: Exocyclic DNA adducts in mutagenesis and carcinogenesis. Singer B, Bartsch H, eds, pp 45-54. International Agency for Research on Cancer, (IARC Sci Publ. No. 150) Lyon, France.
8. de Montarby L, Mosset P, Gree R (1988) Sorbic acid iron tricarbonyl complex as resolving agent. Chiral syntheses of 4-hydroxy nonenal and coriolic acid. Tetrahedron Lett 29: 3937-3940.
9. Esterbauer H, Wegner W (1967) Uber der wirkungen yon aldehyden auf gesundeund maligne zellen. 3. Mitt: Synthesis yon homologen 4-hydroxy-2-alkenale. Monats Chem 98: 1994-2000.
10. 2-deoxyguanosine adducts of trans-4-hydroxynonenal in mammalian cells. Environ Mol Mutagen 42: 68-74.
11. Fujii M, Fukumura M, Hori Y, Hirai Y, Akita H, Nakamura K, Toriizuka K, Ida Y (2006) Chemoenzymatic synthesis of optically active γ-alkyl-γ-butenolides. Tetrahedron: Asymmetry 17: 2292-2298.
12. Gree R, Tourbah H, Carrie R (1986) Fumaraldehyde monodimethyl acetal: an easily accessible and versatile intermediate. Tetrahedron Lett 27: 4983-4986.
13. Hashimoto M, Shibata T, Wasada H, Toyokuni S, Uchida K (2003) Structural basis of protein-bound endogenous aldehydes: chemical and immunochemical characterisations of configurational isomers of a 4-hydroxy-2-nonenal-histidine adduct. J Biol Chem 278: 5044-5051.
14. Kozekov ID, Nechev LV, Moseley MS, Harris CM, Rizzo CJ, Stone MP, Harris TM (2003) DNA interchain cross-links formed by acrolein and crotonaldehyde. J Am Chem Soc 125: 50-61.
15. Kurangi RF, Santosh GT, Blair IA (2006) Convenient and efficient syntheses of 4-hydroxy-2(E)-nonenal and 4-oxo-2(E)-nonenal. Lipids 41: 877-880.
16. 2-Deoxyguanosine adducts of acrolein, crotonaldehyde, and trans-4-hydroxynonenal cross-link to peptides via Schiff base linkage. J Biol Chem 278: 5970-5976.
17. Poli G, Schaur RJ, Siems WG, Leonarduzzi G (2008) 4-Hydroxynonenal: a membrane lipid oxidation product of medicinal interest. Med Res Rev 28: 569-631.
18. Soulère L, Queneau Y, Doutheau A (2007) An expeditious synthesis of 4-hydroxy-2(E)-nonenal (4-HNE), its dimethylacetal and of related compounds. Chem Phys Lipids 150: 239-243.
19. Uchida K, Kanematsu M, Sakai K, Matsuda T, Hattori N, Mizuno Y, Suzuki D, Miyata T, Noguchi N, Niki E, Osawa T (1998) Protein-bound acrolein: potential markers for oxidative stress. Proc Natl Acad Sci USA 95: 4882-4887.
20. Wu YH, Lin JK (1995) Determination of aldehydic lipid peroxidation products with dabsylhydrazine by highper-formance liquid chromatography. Anal Chem 67: 1603-1612.
21. Yang Y, Sharma R, Sharma A, Awasthi S, Awasthi CA (2003) Lipid peroxidation and cell cycle signaling: 4-hydroxynonenal, a key molecule in stress mediated signaling. Acta Biochim Polon 50: 319-336.