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Chemical Compound Review:

NCIMech_000236 2-hydroxytetradecanoic acid

Synonyms: AG-E-75759, AG-L-63468, BSPBio_001417, KBioGR_000137, KBioSS_000137, ...

Kim, B.C. et al., Chen, H.Q. et al., Vaandrager, A.B. et al., Ishitani, M. et al., Matsunaga, I. et al., et al.

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Disease relevance of alpha-Hydroxymyristic acid

Here, we describe cloning of the FAAH gene from Sphingomonas paucimobilis, a sphingolipid- and 2-hydroxymyristic acid-rich bacterium [1].

High impact information on alpha-Hydroxymyristic acid

Treatment of young Arabidopsis seedlings with the myristoylation inhibitor 2-hydroxymyristic acid caused the swelling of root tips, mimicking the phenotype of the salt-hypersensitive mutant sos3-1 [2].
Moreover, incubation of cGK II-expressing 293 cells with the myristoylation inhibitor 2-hydroxymyristic acid (1 mM) significantly increased the proportion of cGK II in the cytosol from 10 +/- 5 to 35 +/- 4% [3].
Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck [4].
In cultured cells, however, 2-hydroxymyristic acid was by far the more effective inhibitor of protein myristoylation [5].
2-Bromopalmitate, a structurally distinct inhibitor of protein palmitoylation, but not 2-hydroxymyristic acid, an inhibitor of protein myristoylation, also reduced (-67%) IL-1 beta-induced NO release from HIT cells [6].

Biological context of alpha-Hydroxymyristic acid

Strain SA3 was identified as a Sphingomonas sp., based on the partial nucleotide sequence analysis of 16S ribosomal RNA, the presence of 2-hydroxymyristic acid (14:O 2-OH) and sphingolipids with d-17:0, d-18:0, d-19:1, and d-20:1 as the main dihydrosphingosines [7].

References

Molecular cloning and expression of fatty acid alpha-hydroxylase from Sphingomonas paucimobilis. Matsunaga, I., Yokotani, N., Gotoh, O., Kusunose, E., Yamada, M., Ichihara, K. J. Biol. Chem. (1997) [Pubmed]
SOS3 function in plant salt tolerance requires N-myristoylation and calcium binding. Ishitani, M., Liu, J., Halfter, U., Kim, C.S., Shi, W., Zhu, J.K. Plant Cell (2000) [Pubmed]
N-terminal myristoylation is required for membrane localization of cGMP-dependent protein kinase type II. Vaandrager, A.B., Ehlert, E.M., Jarchau, T., Lohmann, S.M., de Jonge, H.R. J. Biol. Chem. (1996) [Pubmed]
Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. Nadler, M.J., Harrison, M.L., Ashendel, C.L., Cassady, J.M., Geahlen, R.L. Biochemistry (1993) [Pubmed]
Metabolic activation of 2-substituted derivatives of myristic acid to form potent inhibitors of myristoyl CoA:protein N-myristoyltransferase. Paige, L.A., Zheng, G.Q., DeFrees, S.A., Cassady, J.M., Geahlen, R.L. Biochemistry (1990) [Pubmed]
Novel roles for palmitoylation of Ras in IL-1 beta-induced nitric oxide release and caspase 3 activation in insulin-secreting beta cells. Chen, H.Q., Tannous, M., Veluthakal, R., Amin, R., Kowluru, A. Biochem. Pharmacol. (2003) [Pubmed]
Degradation of polyvinyl alcohol by Sphingomonas sp. SA3 and its symbiote. Kim, B.C., Sohn, C.K., Lim, S.K., Lee, J.W., Park, W. J. Ind. Microbiol. Biotechnol. (2003) [Pubmed]

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