page_title: Nebraskanic acid
section_title: Biosynthesis
hierarchical_section_title: Nebraskanic acid / Biosynthesis
caption_attribution_description: English: Discontinuous elongation pathway for nebraskanic acid biosynthesis.
context_page_description: Nebraskanic acid is a 24-carbon dihydroxy fatty acid with the chemical formula C
  ₂₄H
  ₄₆O
  ₄ and molecular weight 398.6 g/mol.
  Nebraskanic acid was identified as a major component of the seed oil of Chinese violet cress. This fatty acid also occurs in Chinese violet cress oil with a second 24-carbon dihydroxy fatty acid wuhanic acid [-7,18-dihydroxytetracosa-15,21-dienoic acid]. Nebraskanic and wuhanic acids were named in recognition of the location of their co-discoverers at the University of Nebraska-Lincoln and Huazhong Agricultural University, Wuhan, Hubei, China.
context_section_description: The proposed biosynthetic pathway of nebraskanic acid is based on biochemical and genetic data obtained from Chinese violet cress seeds.  These data are consistent with a biosynthetic pathway that originates from the 12-hydroxylation of oleoyl-CoA by a variant fatty acid desaturase 2 (FAD2) enzyme, followed by partial elongation to a C20 3-OH-CoA intermediate. This intermediate is pulled from the elongation cycle through a process termed "discontinuos elongation" by a variant 3-keotacyl-CoA synthetase or FAE1 and elongated through a continuous or complete cycle.  The resulting C22 5-OH fatty acyl-CoA then goes through a continuous elongation cycle that results in the hydroxyl group at the C-7 carbon of the 24-carbon fatty acid chain.  This pathway for the biosynthesis of the C-7 hydroxyl group of nebraskanic acid is conceptually similar to the anaerobic pathway for fatty acid desaturation in bacteria. This pathway is genetically supported by the reconstruction of nebraskanic acid synthesis in Arabidopsis seeds by co-expression of a 12-fatty acid hydroxylase gene and a variant FAE1 gene from Orychophragmus violaceus.
caption: Discontinuous fatty acid elongation pathway for nebraskanic acid biosynthesis.
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