2.02015-09-08 19:48:38 -06002015-12-09 12:10:09 -0700ECMDB24593M2MDB006710PS(14:0/15:0cyclo)PS(14:0/15:0cyclo) is a phosphatidylserine. It is a glycerophospholipid in which a phosphorylserine moiety occupies a glycerol substitution site. As is the case with diacylglycerols, phosphatidylserines can have many different combinations of fatty acids of varying lengths and saturation attached to the C-1 and C-2 atoms.. PS(14:0/15:0cyclo), in particular, consists of one tetradecanoyl chain to the C-1 atom, and one cis-9,10-Methylenetetradecanoic acid to the C-2 atom. Phosphatidylserine or 1,2-diacyl-sn-glycero-3-phospho-L-serine is distributed widely among animals, plants and microorganisms. Phosphatidylserine is an acidic (anionic) phospholipid with three ionizable groups, i.e. the phosphate moiety, the amino group and the carboxyl function. As with other acidic lipids, it exists in nature in salt form, but it has a high propensity to chelate to calcium via the charged oxygen atoms of both the carboxyl and phosphate moieties, modifying the conformation of the polar head group. This interaction may be of considerable relevance to the biological function of phosphatidylserine. While most phospholipids have a saturated fatty acid on C-1 and an unsaturated fatty acid on C-2 of the glycerol backbone, the fatty acid distribution at the C-1 and C-2 positions of glycerol within phospholipids is continually in flux, owing to phospholipid degradation and the continuous phospholipid remodeling that occurs while these molecules are in membranes. Phosphatidylserines typically carry a net charge of -1 at physiological pH. They mostly have palmitic or stearic acid on carbon 1 and a long chain unsaturated fatty acid (e.g. 18:2, 20:4 and 22:6) on carbon 2. PS biosynthesis involves an exchange reaction of serine for ethanolamine in PE.C35H66NO10P691.884691.442434327(2S)-2-amino-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acid(2S)-2-amino-3-{[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCC)C(O)=OInChI=1S/C35H66NO10P/c1-3-5-7-8-9-10-11-12-13-16-19-23-33(37)43-26-31(27-44-47(41,42)45-28-32(36)35(39)40)46-34(38)24-20-17-14-15-18-22-30-25-29(30)21-6-4-2/h29-32H,3-28,36H2,1-2H3,(H,39,40)(H,41,42)/t29?,30?,31-,32+/m1/s1BKGQYQWUYBSINS-JWWJSXKFSA-Nlogp3.56logs-6.57solubility1.84e-04 g/llogp7.38pka_strongest_acidic1.47pka_strongest_basic9.38iupac(2S)-2-amino-3-({[(2R)-2-{[8-(2-butylcyclopropyl)octanoyl]oxy}-3-(tetradecanoyloxy)propoxy](hydroxy)phosphoryl}oxy)propanoic acidaverage_mass691.884mono_mass691.442434327smiles[H][C@](N)(COP(O)(=O)OC[C@@]([H])(COC(=O)CCCCCCCCCCCCC)OC(=O)CCCCCCCC1CC1CCCC)C(O)=OformulaC35H66NO10PinchiInChI=1S/C35H66NO10P/c1-3-5-7-8-9-10-11-12-13-16-19-23-33(37)43-26-31(27-44-47(41,42)45-28-32(36)35(39)40)46-34(38)24-20-17-14-15-18-22-30-25-29(30)21-6-4-2/h29-32H,3-28,36H2,1-2H3,(H,39,40)(H,41,42)/t29?,30?,31-,32+/m1/s1inchikeyBKGQYQWUYBSINS-JWWJSXKFSA-Npolar_surface_area171.68refractivity181.12polarizability80.1rotatable_bond_count35acceptor_count7donor_count3physiological_charge-1formal_charge0phospholipid biosynthesis CL(15:0cyclo/16:1(9Z)/15:0cyclo/14:0)"Phospholipids are membrane components in E. coli.
The major phospholipids of E. coli are phosphatidylethanolamine, phosphatidylglycerol and cardiolipin. All phospholipids contain sn-glycerol-3-phosphate esterified with fatty acids at the sn-1 and sn-2 positions.
The reaction starts from a glycerone phosphate (dihydroxyacetone phosphate) produced in glycolysis. The glycerone phosphate is transformed to a sn-glycerol 3-phosphate (glycerol 3 phosphate) by NADPH driven glycerol-3-phosphate dehydrogenase.
Sn-glycerol 3-phosphate is transformed to a 1-acyl-sn-glycerol 3-phosphate(1-oleyl-2-lyso-phosphatidate , 1-palmitoylglycerol 3-phosphate , 1-stearoyl-sn-glycerol 3-phosphate). This can be achieve by a sn-glycerol-3-phosphate 1-0-acyltransferase that interacts either with a long-chain acyl-CoA or with an acyl-[acp]. The 1-acyl-sn-glycerol 3-phosphate is transformed into a 1,2-diacyl-sn-glycerol 3-phosphate through a 1-acylglycerol-3-phosphate O-acyltransferase.
This compound is then converted into a CPD-diacylglycerol through a CTP (phosphatidate cytididyltransferase. CPD-diacylglycerol can be transformed either to a L-1-phosphatidylserine or a L-1-phosphatidylglycerol-phosphate through a phosphatidylserine synthase or a phosphatidylglycerophosphate synthase respectively. The L-1-phosphatidylserine transforms into L-1-phosphatidylethanolamine through a phosphatidylserine decarboxylase, o the other hand L-1-phosphatidylglycerol-phosphate gets transformed into a L-1-phosphatidyl-glycerol through a phosphatidylglycerophosphatase. These 2 products combines produce a cardiolipin and a ethanolamine.
The L-1 phosphatidyl-glycerol can also interact with cardiolipin synthase resulting in a glycerol and a cardiolipin."PW001119MetabolicSpecdb::CMs1087260Specdb::EiMs4329Specdb::NmrOneD304811Specdb::NmrOneD304812Specdb::NmrOneD304813Specdb::NmrOneD304814Specdb::NmrOneD304815Specdb::NmrOneD304816Specdb::NmrOneD304817Specdb::NmrOneD304818Specdb::NmrOneD304819Specdb::NmrOneD304820Specdb::NmrOneD304821Specdb::NmrOneD304822Specdb::NmrOneD304823Specdb::NmrOneD304824Specdb::NmrOneD304825Specdb::NmrOneD304826Specdb::NmrOneD304827Specdb::NmrOneD304828Specdb::NmrOneD304829Specdb::NmrOneD304830Specdb::MsMs3629013Specdb::MsMs3629014Specdb::MsMs3629015Specdb::MsMs3629016Specdb::MsMs3629017Specdb::MsMs3629018Specdb::MsMs3629019Specdb::MsMs3629020Specdb::MsMs3629021Specdb::MsMs3629022Specdb::MsMs3629023Specdb::MsMs3629024Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590.21097882Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114.22080510Yurtsever D. (2007). Fatty acid methyl ester profiling of Enterococcus and Esherichia coli for microbial source tracking. M.sc. Thesis. Villanova University: U.S.AThompson JA, Miles BS, Fennessey PV: Urinary organic acids quantitated by age groups in a healthy pediatric population. Clin Chem. 1977 Sep;23(9):1734-8.890917Chen S: Partial characterization of the molecular species of phosphatidylserine from human plasma by high-performance liquid chromatography and fast atom bombardment mass spectrometry. J Chromatogr B Biomed Appl. 1994 Nov 4;661(1):1-5.7866537Gao F, Tian X, Wen D, Liao J, Wang T, Liu H: Analysis of phospholipid species in rat peritoneal surface layer by liquid chromatography/electrospray ionization ion-trap mass spectrometry. Biochim Biophys Acta. 2006 Jul;1761(7):667-76. Epub 2006 Apr 24.16714143Phosphatidylserine decarboxylase proenzymeP0A8K1PSD_ECOLIpsdhttp://ecmdb.ca/proteins/P0A8K1.xmlPS(14:0/15:0cyclo) + Hydrogen ion > PE(14:0/15:0cyclo) + Carbon dioxidePW_R005814