MetaCyc Pathway: palmitoleate biosynthesis II (plants and bacteria)
Inferred from experiment

Enzyme View:

Pathway diagram: palmitoleate biosynthesis II (plants and bacteria)

This view shows enzymes only for those organisms listed below, in the list of taxa known to possess the pathway. If an enzyme name is shown in bold, there is experimental evidence for this enzymatic activity.

Synonyms: palmitoleic acid biosynthesis

Superclasses: BiosynthesisFatty Acid and Lipid BiosynthesisFatty Acid BiosynthesisUnsaturated Fatty Acid BiosynthesisPalmitoleate Biosynthesis

Some taxa known to possess this pathway include : Arabidopsis thaliana col, Asclepias syriaca, Psychrobacter urativorans

Expected Taxonomic Range: Bacteria , Eukaryota

Palmitoleate (16:1Δ9) is a common unsaturated fatty acid, found in bacteria, fungi [Casey94], plants [Gibson93] and animals [Goeransson65, Keith67]. It comprises from 10% to 65% of the seed oil of several plants.

Palmitoleate can be formed directly from the saturated fatty acid palmitate by the action of Δ9 desaturase enzymes. Such enzymes have been reported from cyanobacteria [Sakamoto94, Kiseleva00, Chintalapati06, Maali07], fungi [Stukey89, MacKenzie02], higher plants [Marillia02, Lindqvist96], fish [Chang01a] and mammals [Miyazaki06].

Desaturase enzyme do not operate on a free acid substrate. Three types of desaturases are known, that act on acyl-CoA, acyl-[acp], and acyl-lipid conjugates, respectively. In many bacteria and some plants palmitoleate is derived from a palmitoyl-[acp], as shown in this pathway [Cahoon97]. In mammals the enzyme acts only on CoA-derivatives [Miyazaki06], while in some plants and cyanobacteria the desaturase acts on fatty acids embedded within the structure of lipids [Sakamoto94] (see palmitoleate biosynthesis III (cyanobacteria)).

For an alternative pathway for the biosynthesis of palmitoleate, found in the bacterium Escherichia coli, see palmitoleate biosynthesis I (from (5Z)-dodec-5-enoate).

Variants: palmitoleate biosynthesis I (from (5Z)-dodec-5-enoate), palmitoleate biosynthesis III (cyanobacteria)

Created 05-Oct-2006 by Zhang P, TAIR
Revised 11-Jul-2008 by Caspi R, SRI International


Cahoon97: Cahoon EB, Coughlan SJ, Shanklin J (1997). "Characterization of a structurally and functionally diverged acyl-acyl carrier protein desaturase from milkweed seed." Plant Mol Biol 33(6);1105-10. PMID: 9154992

Casey94: Casey WM, Gibson KJ, Parks LW (1994). "Covalent attachment of palmitoleic acid (C16:1 delta 9) to proteins in Saccharomyces cerevisiae. Evidence for a third class of acylated proteins." J Biol Chem 269(3);2082-5. PMID: 8294460

Chang01a: Chang BE, Hsieh SL, Kuo CM (2001). "Molecular cloning of full-length cDNA encoding delta-9 desaturase through PCR strategies and its genomic organization and expression in grass carp (Ctenopharyngodon idella)." Mol Reprod Dev 58(3);245-54. PMID: 11170264

Chintalapati06: Chintalapati S, Prakash JS, Gupta P, Ohtani S, Suzuki I, Sakamoto T, Murata N, Shivaji S (2006). "A novel Delta9 acyl-lipid desaturase, DesC2, from cyanobacteria acts on fatty acids esterified to the sn-2 position of glycerolipids." Biochem J 398(2);207-14. PMID: 16689682

Gibson93: Gibson KJ (1993). "Palmitoleate formation by soybean stearoyl-acyl carrier protein desaturase." Biochim Biophys Acta 1169(3);231-5. PMID: 7548115

Goeransson65: Goeransson G (1965). "The metabolism of fatty acids in the rat. V. palmitoleic acid." Acta Physiol Scand 63;428-33. PMID: 14321753

Keith67: Keith AD (1967). "Fatty acid metabolism in D. melanogaster: formation of palmitoleate." Life Sci 6(2);213-8. PMID: 6030882

Kiseleva00: Kiseleva LL, Serebriiskaya TS, Horvath I, Vigh L, Lyukevich AA, Los DA (2000). "Expression of the gene for the delta9 acyl-lipid desaturase in the thermophilic cyanobacterium." J Mol Microbiol Biotechnol 2(3);331-8. PMID: 10937442

Lindqvist96: Lindqvist Y, Huang W, Schneider G, Shanklin J (1996). "Crystal structure of delta9 stearoyl-acyl carrier protein desaturase from castor seed and its relationship to other di-iron proteins." EMBO J 15(16);4081-92. PMID: 8861937

Maali07: Maali R, Shimshilashvili KhR, Pchelkin VP, Tsydendambaev VD, Nosov AM, Los' DA, Goldenkova-Pavlova IV (2007). "[Comparative expression in Escherichia coli of the native and hybrid genes for acyl-lipid delta(9) desaturase]." Genetika 43(2);176-82. PMID: 17385315

MacKenzie02: MacKenzie DA, Carter AT, Wongwathanarat P, Eagles J, Salt J, Archer DB (2002). "A third fatty acid delta9-desaturase from Mortierella alpina with a different substrate specificity to ole1p and ole2p." Microbiology 148(Pt 6);1725-35. PMID: 12055292

Marillia02: Marillia EF, Giblin EM, Covello PS, Taylor DC (2002). "A desaturase-like protein from white spruce is a Delta(9) desaturase." FEBS Lett 526(1-3);49-52. PMID: 12208502

Miyazaki06: Miyazaki M, Bruggink SM, Ntambi JM (2006). "Identification of mouse palmitoyl-coenzyme A Delta9-desaturase." J Lipid Res 47(4);700-4. PMID: 16443825

Sakamoto94: Sakamoto T, Wada H, Nishida I, Ohmori M, Murata N (1994). "delta 9 Acyl-lipid desaturases of cyanobacteria. Molecular cloning and substrate specificities in terms of fatty acids, sn-positions, and polar head groups." J Biol Chem 269(41);25576-80. PMID: 7929259

Stukey89: Stukey JE, McDonough VM, Martin CE (1989). "Isolation and characterization of OLE1, a gene affecting fatty acid desaturation from Saccharomyces cerevisiae." J Biol Chem 264(28);16537-44. PMID: 2674136

Other References Related to Enzymes, Genes, Subpathways, and Substrates of this Pathway

Bonner72: Bonner WM, Bloch K (1972). "Purification and properties of fatty acyl thioesterase I from Escherichia coli." J Biol Chem 1972;247(10);3123-33. PMID: 4554913

Buist04: Buist PH (2004). "Fatty acid desaturases: selecting the dehydrogenation channel." Nat Prod Rep 21(2);249-62. PMID: 15042148

Byers07: Byers DM, Gong H (2007). "Acyl carrier protein: structure-function relationships in a conserved multifunctional protein family." Biochem Cell Biol 85(6);649-62. PMID: 18059524

Latendresse13: Latendresse M. (2013). "Computing Gibbs Free Energy of Compounds and Reactions in MetaCyc."

Li08a: Li Y, Dietrich M, Schmid RD, He B, Ouyang P, Urlacher VB (2008). "Identification and functional expression of a Delta9-fatty acid desaturase from Psychrobacter urativorans in Escherichia coli." Lipids 43(3);207-13. PMID: 18256868

Park06: Park YJ, Yoo CB, Choi SY, Lee HB (2006). "Purifications and characterizations of a ferredoxin and its related 2-oxoacid:ferredoxin oxidoreductase from the hyperthermophilic archaeon, Sulfolobus solfataricus P1." J Biochem Mol Biol 39(1);46-54. PMID: 16466637

Salas02: Salas JJ, Ohlrogge JB (2002). "Characterization of substrate specificity of plant FatA and FatB acyl-ACP thioesterases." Arch Biochem Biophys 403(1);25-34. PMID: 12061798

Shanklin91: Shanklin J, Somerville C (1991). "Stearoyl-acyl-carrier-protein desaturase from higher plants is structurally unrelated to the animal and fungal homologs." Proc Natl Acad Sci U S A 88(6);2510-4. PMID: 2006187

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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