Details

Autor(en) / Beteiligte

• Woodcock, Steven R
• Salvatore, Sonia R
• Bonacci, Gustavo
• Schopfer, Francisco J
• Freeman, Bruce A

Titel

Biomimetic Nitration of Conjugated Linoleic Acid: Formation and Characterization of Naturally Occurring Conjugated Nitrodienes

Ist Teil von

• Journal of organic chemistry, 2014-01, Vol.79 (1), p.25-33

Ort / Verlag

United States: American Chemical Society

Erscheinungsjahr

2014

Link zum Volltext

Quelle

MEDLINE

Beschreibungen/Notizen

• Nitro-conjugated linoleic acids (NO2-cLA), endogenous nitrodiene lipids which act as inflammatory signaling mediators, were isolated and single isomers purified from the biomimetic acidic nitration products of conjugated linoleic acid (CLA). Structures were elucidated by means of detailed NMR and HPLC–MS/MS spectroscopic analysis and the relative double bond configurations assigned. Additional synthetic methods produced useful quantities and similar isomeric distributions of these unusual and reactive compounds for biological studies and isotopic standards, and the potential conversion of nitro-linoleic to nitro-conjugated linoleic acids was explored via a facile base-catalyzed isomerization. This represents one of the few descriptions of naturally occurring conjugated nitro dienes (in particular, 1-nitro 1,3-diene), an unusual and highly reactive motif with few biological examples extant.