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:||Biosynthesis → Fatty Acid and Lipid Biosynthesis → Fatty Acid Biosynthesis → Unsaturated Fatty Acid Biosynthesis → Palmitoleate Biosynthesis|
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 [Sakamoto94a, Kiseleva00, Chintalapati06, Maali07], fungi [Stukey89, MacKenzie02], higher plants [Marillia02, Lindqvist96], fish [Chang01] and mammals [Miyazaki06a].
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 [Miyazaki06a], while in some plants and cyanobacteria the desaturase acts on fatty acids embedded within the structure of lipids [Sakamoto94a] (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).
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
Chang01: 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
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
Sakamoto94a: 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
Li08: 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
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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