2.0 2012-05-31 14:58:17 -0600 2015-06-03 17:20:37 -0600 ECMDB21089 M2MDB001505 LPS (4-O-antigen) Lipopolysaccharides (LPS), also known as lipoglycans, are large molecules consisting of a lipid and a polysaccharide joined by a covalent bond; they are found in the outer membrane of Gram-negative bacteria, act as endotoxins and elicit strong immune responses in animals. LPS consists of three parts: O antigen (or O polysaccharide), core polysaccharide and lipid A.When LPS contains a repetitive glycan polymer this is referred to as the O antigen, O polysaccharide, or O side chain of the bacteria. LPS (1-o-antigen) contains four units of O antigen. The O antigen is attached to the core oligosaccharide, and comprises the outermost domain of the LPS molecule. The composition of the O chain varies from strain to strain, for example there are over 160 different O antigen structures produced by different E. coli strains. The presence or absence of O chains determine whether the LPS is considered rough or smooth. Full length O-chains would render the LPS smooth while the absence or reduction of O-chains would make the LPS rough. Bacteria with rough LPS usually have more penetrable cell membranes to hydrophobic antibiotics since a rough LPS is more hydrophobic. O antigen is exposed on the very outer surface of the bacterial cell, and as a consequence, is a target for recognition by host antibodies. Lipopolysaccharide C320H560N22O198P6 8069.7416 8065.285310258 (2R,3S,4R,5R,6R)-5-{[(3S,4R,5R,6R)-5-[({[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]-4-{[(3S,4S,5R,6R)-4-{[(3R,4S,5R,6R)-4-{[(2R,3R,4S,5R,6R)-3-{[(3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(2R,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-6-[(2S)-1-{[(3S,4R,5S,6R)-3,4-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]-5-(phosphonooxy)oxan-2-yl]oxy}propan-2-yl]-3,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-4-{[(2S,3S,4S,5R,6R)-4-{[(2S,3S,4S,5R,6R)-4-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-carboxy-3,5-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-2-carboxy-3,5-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-{[(3R)-1,3-dihydroxytetradecylidene]amino}-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[(3R)-3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-3-(phosphonooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-3-hydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxane-2-carboxylic acid (2R,3S,4R,5R,6R)-5-{[(3S,4R,5R,6R)-5-({[2-aminoethoxy(hydroxy)phosphoryl]oxy(hydroxy)phosphoryl}oxy)-4-{[(3S,4S,5R,6R)-4-{[(3R,4S,5R,6R)-4-{[(2R,3R,4S,5R,6R)-3-{[(3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-(C-hydroxycarbonimidoylamino)-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(C-hydroxycarbonimidoylamino)-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(C-hydroxycarbonimidoylamino)-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(C-hydroxycarbonimidoylamino)-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-(C-hydroxycarbonimidoylamino)-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(2R,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-6-[(2S)-1-{[(3S,4R,5S,6R)-3,4-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]-5-(phosphonooxy)oxan-2-yl]oxy}propan-2-yl]-3,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-4-{[(2S,3S,4S,5R,6R)-4-{[(2S,3S,4S,5R,6R)-4-{[2-aminoethoxy(hydroxy)phosphoryl]oxy}-2-carboxy-3,5-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-2-carboxy-3,5-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-{[(3R)-1,3-dihydroxytetradecylidene]amino}-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[(3R)-3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-3-(phosphonooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-3-hydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxane-2-carboxylic acid P(O[C@]1(O[C@@]([H])([C@@]([H])(O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@]1(N=C(O)C[C@]([H])(O)CCCCCCCCCCC)[H])CO[C@@]1(O[C@]([H])(CO[C@]2(O[C@]([H])([C@@]([H])(C)CO)[C@]([H])([C@@](O[C@]3(O[C@]([H])([C@@]([H])(C)CO)[C@@]([H])(O)[C@@](O[C@]4(O[C@]([H])([C@@]([H])(C)CO)[C@@]([H])(O)[C@@](OP(O)(=O)OCCN)([H])[C@]4([H])O)C(O)=O)([H])[C@]3([H])O)C(O)=O)([H])[C@]2([H])O)OC2(O[C@]([H])([C@@]([H])(C)CO)[C@](OP(OP(O)(=O)OCCN)(O)=O)([H])[C@@]([H])([C@]2([H])O)OC2(O[C@]([H])([C@@]([H])(C)COC3(O[C@]([H])([C@@]([H])(C)CO)[C@](OP(O)(O)=O)([H])[C@]([H])(O)[C@]3([H])O)[H])[C@@]([H])(O)[C@@]([H])([C@]2([H])O)OC2(O[C@@]([H])([C@@]([H])(O)[C@@]([H])([C@@]2([H])O)O[C@]2(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]2([H])OC2(O[C@@]([H])([C@@]([H])(O)[C@@]([H])([C@@]2([H])O[C@@]2(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]2([H])NC(O)=N)CO)[H])O[C@@]2(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]2(N=C(C)O)[H])O[C@@]2(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]3(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]3([H])O[C@@]3(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]3(N=C(C)O)[H])O[C@@]3(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]4(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]4([H])O[C@@]4(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]4(N=C(C)O)[H])O[C@@]4(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]5(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]5([H])O[C@@]5(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]5(N=C(C)O)[H])O[C@@]5(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]6(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]6([H])O)CO[C@]6(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]6([H])O)CO)[H])[H])[C@]5(N=C(C)O)[H])CO)[H])CO[C@@]5(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]5([H])NC(O)=N)CO)[H])[H])CO[C@]5(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]5([H])O)CO)[H])[H])[C@]4(N=C(C)O)[H])CO)[H])CO[C@@]4(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]4([H])NC(O)=N)CO)[H])[H])CO[C@]4(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)CO)[H])[H])[C@]3(N=C(C)O)[H])CO)[H])CO[C@@]3(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]3([H])NC(O)=N)CO)[H])[H])CO[C@]3(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)CO)[H])[H])[C@]2(N=C(C)O)[H])CO)[H])CO[C@@]2(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]2([H])NC(O)=N)CO)[H])[H])CO)[H])CO)[H])CO[C@]2(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)CO)[H])[H])[H])[H])C(O)=O)[C@](OP(O)(O)=O)([H])[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@]1(N=C(O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[H])[H])[H])(O)(O)=O InChI=1S/C320H560N22O198P6/c1-21-27-33-39-45-51-52-58-64-70-76-82-172(377)479-141(80-74-68-62-56-49-43-37-31-25-5)90-174(379)508-261-189(337-170(375)89-140(79-73-67-61-55-48-42-36-30-24-4)478-171(376)81-75-69-63-57-50-44-38-32-26-6)284(469-121-166-210(400)252(507-173(378)88-139(373)78-72-66-60-54-47-41-35-29-23-3)188(294(500-166)539-543(455,456)457)336-169(374)87-138(372)77-71-65-59-53-46-40-34-28-22-2)506-168(251(261)535-541(449,450)451)123-475-318(310(438)439)279(437)275(534-319(311(440)441)277(435)267(240(430)246(530-319)124(7)91-343)533-320(312(442)443)278(436)268(537-544(458,459)476-85-83-321)241(431)247(531-320)125(8)92-344)273(250(532-318)128(11)95-347)528-304-244(434)265(274(249(511-304)127(10)94-346)538-546(462,463)540-545(460,461)477-86-84-322)523-303-243(433)263(239(429)245(509-303)129(12)112-464-300-238(428)231(421)266(536-542(452,453)454)248(510-300)126(9)93-345)520-302-242(432)262(215(405)167(502-302)122-474-299-236(426)225(415)199(389)151(105-357)493-299)521-305-272(227(417)200(390)152(106-358)494-305)527-309-276(529-285-179(342-317(327)448)220(410)194(384)146(100-352)484-285)264(209(399)157(111-363)495-309)522-290-184(332-134(17)368)257(211(401)162(496-290)117-465-280-175(338-313(323)444)216(406)190(380)142(96-348)480-280)512-287-181(329-131(14)365)254(206(396)154(108-360)486-287)517-306-270(229(419)203(393)159(503-306)114-471-296-233(423)222(412)196(386)148(102-354)490-296)525-292-186(334-136(19)370)259(213(403)164(498-292)119-467-282-177(340-315(325)446)218(408)192(382)144(98-350)482-282)514-289-183(331-133(16)367)256(208(398)156(110-362)488-289)519-308-271(230(420)204(394)161(505-308)116-473-298-235(425)224(414)198(388)150(104-356)492-298)526-293-187(335-137(20)371)260(214(404)165(499-293)120-468-283-178(341-316(326)447)219(409)193(383)145(99-351)483-283)515-288-182(330-132(15)366)255(207(397)155(109-361)487-288)518-307-269(228(418)202(392)160(504-307)115-472-297-234(424)223(413)197(387)149(103-355)491-297)524-291-185(333-135(18)369)258(212(402)163(497-291)118-466-281-176(339-314(324)445)217(407)191(381)143(97-349)481-281)513-286-180(328-130(13)364)253(205(395)153(107-359)485-286)516-301-237(427)226(416)201(391)158(501-301)113-470-295-232(422)221(411)195(385)147(101-353)489-295/h124-129,138-168,175-309,343-363,372-373,380-437H,21-123,321-322H2,1-20H3,(H,328,364)(H,329,365)(H,330,366)(H,331,367)(H,332,368)(H,333,369)(H,334,370)(H,335,371)(H,336,374)(H,337,375)(H,438,439)(H,440,441)(H,442,443)(H,458,459)(H,460,461)(H,462,463)(H3,323,338,444)(H3,324,339,445)(H3,325,340,446)(H3,326,341,447)(H3,327,342,448)(H2,449,450,451)(H2,452,453,454)(H2,455,456,457) MNCUCRNHEGQSDI-UHFFFAOYSA-N Solid Cytoplasm Membrane Periplasm logp -22 ChemAxon pka_strongest_acidic 0.38 ChemAxon iupac (2R,3S,4R,5R,6R)-5-{[(3S,4R,5R,6R)-5-[({[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]-4-{[(3S,4S,5R,6R)-4-{[(3R,4S,5R,6R)-4-{[(2R,3R,4S,5R,6R)-3-{[(3R,4S,5R,6R)-3-{[(2S,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-4-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-{[(2R,3R,4R,5R,6R)-4-{[(2S,3R,4S,5R,6R)-3-{[(2S,3R,4R,5R,6R)-6-({[(2R,3R,4R,5S,6R)-4,5-dihydroxy-3-[(C-hydroxycarbonimidoyl)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-5-hydroxy-4-{[(2R,3R,4R,5R,6R)-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)-4-{[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-4,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-5-hydroxy-3-[(1-hydroxyethylidene)amino]oxan-2-yl]oxy}-5-hydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxy-6-({[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-6-[(2S)-1-{[(3S,4R,5S,6R)-3,4-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]-5-(phosphonooxy)oxan-2-yl]oxy}propan-2-yl]-3,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-4-{[(2S,3S,4S,5R,6R)-4-{[(2S,3S,4S,5R,6R)-4-{[(2-aminoethoxy)(hydroxy)phosphoryl]oxy}-2-carboxy-3,5-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-2-carboxy-3,5-dihydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxan-2-yl]oxy}-2-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-5-{[(3R)-1,3-dihydroxytetradecylidene]amino}-3-hydroxy-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-5-{[(3R)-3-(dodecanoyloxy)-1-hydroxytetradecylidene]amino}-3-(phosphonooxy)-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-3-hydroxy-6-[(2S)-1-hydroxypropan-2-yl]oxane-2-carboxylic acid ChemAxon average_mass 8069.7416 ChemAxon mono_mass 8065.285310258 ChemAxon smiles P(O[C@]1(O[C@@]([H])([C@@]([H])(O)[C@]([H])(OC(=O)C[C@]([H])(O)CCCCCCCCCCC)[C@]1(N=C(O)C[C@]([H])(O)CCCCCCCCCCC)[H])CO[C@@]1(O[C@]([H])(CO[C@]2(O[C@]([H])([C@@]([H])(C)CO)[C@]([H])([C@@](O[C@]3(O[C@]([H])([C@@]([H])(C)CO)[C@@]([H])(O)[C@@](O[C@]4(O[C@]([H])([C@@]([H])(C)CO)[C@@]([H])(O)[C@@](OP(O)(=O)OCCN)([H])[C@]4([H])O)C(O)=O)([H])[C@]3([H])O)C(O)=O)([H])[C@]2([H])O)OC2(O[C@]([H])([C@@]([H])(C)CO)[C@](OP(OP(O)(=O)OCCN)(O)=O)([H])[C@@]([H])([C@]2([H])O)OC2(O[C@]([H])([C@@]([H])(C)COC3(O[C@]([H])([C@@]([H])(C)CO)[C@](OP(O)(O)=O)([H])[C@]([H])(O)[C@]3([H])O)[H])[C@@]([H])(O)[C@@]([H])([C@]2([H])O)OC2(O[C@@]([H])([C@@]([H])(O)[C@@]([H])([C@@]2([H])O)O[C@]2(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]2([H])OC2(O[C@@]([H])([C@@]([H])(O)[C@@]([H])([C@@]2([H])O[C@@]2(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]2([H])NC(O)=N)CO)[H])O[C@@]2(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]2(N=C(C)O)[H])O[C@@]2(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]3(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]3([H])O[C@@]3(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]3(N=C(C)O)[H])O[C@@]3(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]4(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]4([H])O[C@@]4(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]4(N=C(C)O)[H])O[C@@]4(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]5(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]5([H])O[C@@]5(O[C@@]([H])([C@]([H])(O)[C@@]([H])([C@]5(N=C(C)O)[H])O[C@@]5(O[C@@]([H])([C@]([H])(O)[C@]([H])(O[C@]6(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]6([H])O)CO[C@]6(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]6([H])O)CO)[H])[H])[C@]5(N=C(C)O)[H])CO)[H])CO[C@@]5(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]5([H])NC(O)=N)CO)[H])[H])CO[C@]5(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]5([H])O)CO)[H])[H])[C@]4(N=C(C)O)[H])CO)[H])CO[C@@]4(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]4([H])NC(O)=N)CO)[H])[H])CO[C@]4(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]4([H])O)CO)[H])[H])[C@]3(N=C(C)O)[H])CO)[H])CO[C@@]3(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]3([H])NC(O)=N)CO)[H])[H])CO[C@]3(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]3([H])O)CO)[H])[H])[C@]2(N=C(C)O)[H])CO)[H])CO[C@@]2(O[C@@]([H])([C@@]([H])(O)[C@]([H])(O)[C@@]2([H])NC(O)=N)CO)[H])[H])CO)[H])CO)[H])CO[C@]2(O[C@@]([H])([C@]([H])(O)[C@]([H])(O)[C@@]2([H])O)CO)[H])[H])[H])[H])C(O)=O)[C@](OP(O)(O)=O)([H])[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@]1(N=C(O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)[H])[H])[H])(O)(O)=O ChemAxon formula C320H560N22O198P6 ChemAxon inchi InChI=1S/C320H560N22O198P6/c1-21-27-33-39-45-51-52-58-64-70-76-82-172(377)479-141(80-74-68-62-56-49-43-37-31-25-5)90-174(379)508-261-189(337-170(375)89-140(79-73-67-61-55-48-42-36-30-24-4)478-171(376)81-75-69-63-57-50-44-38-32-26-6)284(469-121-166-210(400)252(507-173(378)88-139(373)78-72-66-60-54-47-41-35-29-23-3)188(294(500-166)539-543(455,456)457)336-169(374)87-138(372)77-71-65-59-53-46-40-34-28-22-2)506-168(251(261)535-541(449,450)451)123-475-318(310(438)439)279(437)275(534-319(311(440)441)277(435)267(240(430)246(530-319)124(7)91-343)533-320(312(442)443)278(436)268(537-544(458,459)476-85-83-321)241(431)247(531-320)125(8)92-344)273(250(532-318)128(11)95-347)528-304-244(434)265(274(249(511-304)127(10)94-346)538-546(462,463)540-545(460,461)477-86-84-322)523-303-243(433)263(239(429)245(509-303)129(12)112-464-300-238(428)231(421)266(536-542(452,453)454)248(510-300)126(9)93-345)520-302-242(432)262(215(405)167(502-302)122-474-299-236(426)225(415)199(389)151(105-357)493-299)521-305-272(227(417)200(390)152(106-358)494-305)527-309-276(529-285-179(342-317(327)448)220(410)194(384)146(100-352)484-285)264(209(399)157(111-363)495-309)522-290-184(332-134(17)368)257(211(401)162(496-290)117-465-280-175(338-313(323)444)216(406)190(380)142(96-348)480-280)512-287-181(329-131(14)365)254(206(396)154(108-360)486-287)517-306-270(229(419)203(393)159(503-306)114-471-296-233(423)222(412)196(386)148(102-354)490-296)525-292-186(334-136(19)370)259(213(403)164(498-292)119-467-282-177(340-315(325)446)218(408)192(382)144(98-350)482-282)514-289-183(331-133(16)367)256(208(398)156(110-362)488-289)519-308-271(230(420)204(394)161(505-308)116-473-298-235(425)224(414)198(388)150(104-356)492-298)526-293-187(335-137(20)371)260(214(404)165(499-293)120-468-283-178(341-316(326)447)219(409)193(383)145(99-351)483-283)515-288-182(330-132(15)366)255(207(397)155(109-361)487-288)518-307-269(228(418)202(392)160(504-307)115-472-297-234(424)223(413)197(387)149(103-355)491-297)524-291-185(333-135(18)369)258(212(402)163(497-291)118-466-281-176(339-314(324)445)217(407)191(381)143(97-349)481-281)513-286-180(328-130(13)364)253(205(395)153(107-359)485-286)516-301-237(427)226(416)201(391)158(501-301)113-470-295-232(422)221(411)195(385)147(101-353)489-295/h124-129,138-168,175-309,343-363,372-373,380-437H,21-123,321-322H2,1-20H3,(H,328,364)(H,329,365)(H,330,366)(H,331,367)(H,332,368)(H,333,369)(H,334,370)(H,335,371)(H,336,374)(H,337,375)(H,438,439)(H,440,441)(H,442,443)(H,458,459)(H,460,461)(H,462,463)(H3,323,338,444)(H3,324,339,445)(H3,325,340,446)(H3,326,341,447)(H3,327,342,448)(H2,449,450,451)(H2,452,453,454)(H2,455,456,457) ChemAxon inchikey MNCUCRNHEGQSDI-UHFFFAOYSA-N ChemAxon polar_surface_area 3472.5 ChemAxon refractivity 1822.66 ChemAxon rotatable_bond_count 217 ChemAxon acceptor_count 208 ChemAxon donor_count 120 ChemAxon physiological_charge -2 ChemAxon formal_charge 0 ChemAxon Lipopolysaccharide biosynthesis E. coli lipid A is synthesized on the cytoplasmic surface of the inner membrane. The pathway can start from the fructose 6-phosphate that is either produced in the glycolysis and pyruvate dehydrogenase or be obtained from the interaction with D-fructose interacting with a mannose PTS permease. Fructose 6-phosphate interacts with L-glutamine through a D-fructose-6-phosphate aminotransferase resulting into a L-glutamic acid and a glucosamine 6-phosphate. The latter compound is isomerized through a phosphoglucosamine mutase resulting a glucosamine 1-phosphate. This compound is acetylated, interacting with acetyl-CoA through a bifunctional protein glmU resulting in a Coenzyme A, hydrogen ion and N-acetyl-glucosamine 1-phosphate. This compound interact with UTP and hydrogen ion through the bifunctional protein glmU resulting in a pyrophosphate and a UDP-N-acetylglucosamine. This compound interacts with (3R)-3-hydroxymyristoyl-[acp] through an UDP-N-acetylglucosamine acyltransferase resulting in a holo-[acp] and a UDP-3-O[(3R)-3-hydroxymyristoyl]-N-acetyl-alpha-D-glucosamine. This compound interacts with water through UDP-3-O-acyl-N-acetylglucosamine deacetylase resulting in an acetic acid and UDP-3-O-(3-hydroxymyristoyl)-α-D-glucosamine. The latter compound interacts with (3R)-3-hydroxymyristoyl-[acp] through UDP-3-O-(R-3-hydroxymyristoyl)-glucosamine N-acyltransferase releasing a hydrogen ion, a holo-acp and UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine. The latter compound is hydrolase by interacting with water and a UDP-2,3-diacylglucosamine hydrolase resulting in UMP, hydrogen ion and 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate. This last compound then interacts with a UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine through a lipid A disaccharide synthase resulting in a release of UDP, hydrogen ion and a lipid A disaccharide. The lipid A disaccharide is phosphorylated by an ATP mediated tetraacyldisaccharide 4'-kinase resulting in the release of hydrogen ion and lipid IVA. A D-ribulose 5-phosphate is isomerized with D-arabinose 5-phosphate isomerase 2 to result in a D-arabinose 5-phosphate. This compounds interacts with water and phosphoenolpyruvic acid through a 3-deoxy-D-manno-octulosonate 8-phosphate synthase resulting in the release of phosphate and 3-deoxy-D-manno-octulosonate 8-phosphate. This compound interacts with water through a 3-deoxy-D-manno-octulosonate 8-phosphate phosphatase thus releasing a phosphate and a 3-deoxy-D-manno-octulosonate. The latter compound interacts with CTP through a 3-deoxy-D-manno-octulosonate cytidylyltransferase resulting in a pyrophosphate and CMP-3-deoxy-α-D-manno-octulosonate. CMP-3-deoxy-α-D-manno-octulosonate and lipid IVA interact with each other through a KDO transferase resulting in CMP, hydrogen ion and alpha-Kdo-(2-->6)-lipid IVA. The latter compound reacts with CMP-3-deoxy-α-D-manno-octulosonate through a KDO transferase resulting in a CMP, hydrogen ion, and a a-Kdo-(2->4)-a-Kdo-(2->6)-lipid IVA. The latter compound interacts with a dodecanoyl-[acp] lauroyl acyltransferase resulting in a holo-[acp] and a (KDO)2-(lauroyl)-lipid IVA. The latter compound reacts with a myristoyl-[acp] through a myristoyl-acyl carrier protein (ACP)-dependent acyltransferase resulting in a holo-[acp], (KDO)2-lipid A. The latter compound reacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase I resulting hydrogen ion, ADP, heptosyl-KDO2-lipid A. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through ADP-heptose:LPS heptosyltransferase II resulting in ADP, hydrogen ion and (heptosyl)2-Kdo2-lipid A. The latter compound UDP-glucose interacts with (heptosyl)2-Kdo2-lipid A resulting in UDP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A. Glucosyl-(heptosyl)2-Kdo2-lipid A (Escherichia coli) is phosphorylated through an ATP-mediated lipopolysaccharide core heptose (I) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)2-Kdo2-lipid A-phosphate. The latter compound interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core heptosyl transferase III resulting in ADP, hydrogen ion, and glucosyl-(heptosyl)3-Kdo2-lipid A-phosphate. The latter compound is phosphorylated through an ATP-driven lipopolysaccharide core heptose (II) kinase resulting in ADP, hydrogen ion and glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-alpha-D-galactose through a UDP-D-galactose:(glucosyl)lipopolysaccharide-1,6-D-galactosyltransferase resulting in a UDP, a hydrogen ion and a galactosyl-glucosyl-(heptosyl)3-Kdo2-lipid A-bisphosphate. The latter compound interacts with UDP-glucose through a (glucosyl)LPS α-1,3-glucosyltransferase resulting in a hydrogen ion, a UDP and galactosyl-(glucosyl)2-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with UDP-glucose through a UDP-glucose:(glucosyl)LPS α-1,2-glucosyltransferase resulting in UDP, a hydrogen ion and galactosyl-(glucosyl)3-(heptosyl)3-Kdo2-lipid A-bisphosphate. This compound then interacts with ADP-L-glycero-beta-D-manno-heptose through a lipopolysaccharide core biosynthesis; heptosyl transferase IV; probably hexose transferase resulting in a Lipid A-core. A lipid A-core is then exported into the periplasmic space by a lipopolysaccharide ABC transporter. The lipid A-core is then flipped to the outer surface of the inner membrane by the ATP-binding cassette (ABC) transporter, MsbA. An additional integral membrane protein, YhjD, has recently been implicated in LPS export across the IM. The smallest LPS derivative that supports viability in E. coli is lipid IVA. However, it requires mutations in either MsbA or YhjD, to suppress the normally lethal consequence of an incomplete lipid A . Recent studies with deletion mutants implicate the periplasmic protein LptA, the cytosolic protein LptB, and the IM proteins LptC, LptF, and LptG in the subsequent transport of nascent LPS to the outer membrane (OM), where the LptD/LptE complex flips LPS to the outer surface. PW000831 ec00540 Metabolic ABC transporters ec02010 superpathway of lipopolysaccharide biosynthesis LPSSYN-PWY 11970143 C00338 16412 Keseler, 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. 21097882 Kanehisa, 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. 22080510 Lipopolysaccharide export system permease protein lptG P0ADC6 LPTG_ECOLI lptG http://ecmdb.ca/proteins/P0ADC6.xml Lipopolysaccharide export system permease protein lptF P0AF98 LPTF_ECOLI lptF http://ecmdb.ca/proteins/P0AF98.xml Lipopolysaccharide export system permease protein lptG P0ADC6 LPTG_ECOLI lptG http://ecmdb.ca/proteins/P0ADC6.xml Lipopolysaccharide export system permease protein lptF P0AF98 LPTF_ECOLI lptF http://ecmdb.ca/proteins/P0AF98.xml