2.02012-05-31 14:39:22 -06002015-06-03 17:19:47 -0600ECMDB20325M2MDB001159Decarboxy-SAMdcSAM is a member of the chemical class known as Purine Nucleosides and Analogues. These are compounds comprising a purine base attached to a sugar. [2-(Amino-oxy)ethyl](5'-deoxyadenosin-5'-yl)(methyl)sulphonium+ ++, the amino-oxy analogue of decarboxylated S-adenosylmethionine, is a potent irreversible inhibitor of Escherichia coli S-adenosylmethionine decarboxylase [Khomutov, Zavalova, Syrku, Artamonova & Khomutov (1983) Bioorg. (PMID 1872800)(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulfonium salt(5-deoxy-5-adenosyl)(3-aminopropyl) methylsulphonium salt3-amino-propyl-<i>S</i>-adenosine3-Amino-propyl-S-adenosine<i>S</i>-adenosylmethioninamine<i>S</i>-methyl-<i>S</i>-adenosyl homocysteamineDadometDcSAMDecarboxylated adometDecarboxylated S-adenosylmethionineDecarboxylated samS-Adenosyl-(5')-3-methylthiopropylamineS-Adenosyl-L-methioninamineS-AdenosylmethioninamineS-Methyl-S-adenosyl homocysteamineC14H24N6O3S356.444356.163059354{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-azaniumylpropyl)methylsulfaniumS-adenosylmethioninaminium[H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OInChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/p+1/t8-,10-,11-,14-,24?/m1/s1ZUNBITIXDCPNSD-LSRJEVITSA-OCytoplasmPeriplasmlogp-1.73logs-2.96solubility4.72e-01 g/llogp-2.8pka_strongest_acidic12.45pka_strongest_basic10.09iupac{[(2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl}(3-azaniumylpropyl)methylsulfaniumaverage_mass356.444mono_mass356.163059354smiles[H][C@]1(C[S+](C)CCC[NH3+])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OformulaC14H24N6O3SinchiInChI=1S/C14H23N6O3S/c1-24(4-2-3-15)5-8-10(21)11(22)14(23-8)20-7-19-9-12(16)17-6-18-13(9)20/h6-8,10-11,14,21-22H,2-5,15H2,1H3,(H2,16,17,18)/q+1/p+1/t8-,10-,11-,14-,24?/m1/s1inchikeyZUNBITIXDCPNSD-LSRJEVITSA-Opolar_surface_area146.95refractivity101.7polarizability37.34rotatable_bond_count6acceptor_count7donor_count4physiological_charge2formal_charge2Spermidine Biosynthesis ISpermidine is formed by the addition of a propylamine moiety to putrescine, catalyzed by an aminopropyltransferase termed spermidine synthase, the the product of gene speE. The source of the propylamine group is decarboxylated S-adenosyl-L-methionine (S-adenosyl-L-methioninamine) which is produced by the action of the pyruvoyl-containing enzyme adenosylmethionine decarboxylase. The other product of the aminopropyltransferase reaction is S-methyl-5'-thioadenosine (MTA), which can be recycled back to L-methionine in many organisms, but not in E. coli.
Inhibition of E. coli adenosylmethionine decarboxylase by spermidine appears to be the most significant regulator of polyamine biosynthesis, probably limiting it when the intracellular spermidine concentration becomes excessive. In E. coli most intracellular spermidine is bound to nucleic acids and phospholipids. (EcoCyc)PW002040Metabolicaminopropylcadaverine biosynthesisPolyamines are important for cell growth and are believed to be involved in many processes including DNA, RNA, and protein synthesis, as well as membrane integrity and resistance to stress, to name a few. Cadaverine and aminopropylcadaverine are alternative polyamines that can at least partially substitute for purtrescine and spermidine, the primary polyamines found in E. coli. Lysine is decarboxylated to form cadaverine which is then converted to aminopropylcadaverine by the aminopropyltransferase, SpeE. (EcoCyc)PW002039Metabolicaminopropylcadaverine biosynthesisPWY0-1303spermidine biosynthesis IBSUBPOLYAMSYN-PWYSpecdb::NmrOneD264788Specdb::NmrOneD264789Specdb::NmrOneD264790Specdb::NmrOneD264791Specdb::NmrOneD264792Specdb::NmrOneD264793Specdb::NmrOneD264794Specdb::NmrOneD264795Specdb::NmrOneD264796Specdb::NmrOneD264797Specdb::NmrOneD264798Specdb::NmrOneD264799Specdb::NmrOneD264800Specdb::NmrOneD264801Specdb::NmrOneD264802Specdb::NmrOneD264803Specdb::NmrOneD264804Specdb::NmrOneD264805Specdb::NmrOneD264806Specdb::NmrOneD2648072520349026330790S-ADENOSYLMETHIONINAMINEKeseler, 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-D590.21097882Weitkamp, E. L., Dixon, H. B., Khomutov, A. R., Khomutov, R. M. (1991). "Effect of magnesium ions on the inhibition of S-adenosylmethionine decarboxylase from Escherichia coli by [2-(amino-oxy)ethyl](5'-deoxyadenosin-5'-yl)(methyl)sulphonium ." Biochem J 277 ( Pt 3):643-645.1872800Spermidine synthaseP09158SPEE_ECOLIspeEhttp://ecmdb.ca/proteins/P09158.xmlS-adenosylmethionine decarboxylase proenzymeP0A7F6SPED_ECOLIspeDhttp://ecmdb.ca/proteins/P0A7F6.xmlS-adenosyl-L-methionine + Hydrogen ion > Decarboxy-SAM + Carbon dioxidePW_R005960Cadaverine + Decarboxy-SAM > Aminopropylcadaverine + 5'-Methylthioadenosine + Hydrogen ionPW_R005959Decarboxy-SAM + Putrescine > 5'-Methylthioadenosine + Spermidine + Hydrogen ionPW_R005961