4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A (PAMDB001582)
Record Information | ||||||||||||||||||||||||||||||||||||||||||||||
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Version | 1.0 | |||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 12:54:54 PM | |||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB001582 | |||||||||||||||||||||||||||||||||||||||||||||
Identification | ||||||||||||||||||||||||||||||||||||||||||||||
Name: | 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A | |||||||||||||||||||||||||||||||||||||||||||||
Description: | 4-amino-4-deoxy-l-arabinose modified core oligosaccharide lipid a belongs to the class of Polyhexoses. These are polysaccharides in which the saccharide units are hexoses. (inferred from compound structure) | |||||||||||||||||||||||||||||||||||||||||||||
Structure | ||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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Chemical Formula: | C181H314N3O103P4 | |||||||||||||||||||||||||||||||||||||||||||||
Average Molecular Weight: | 4304.2832 | |||||||||||||||||||||||||||||||||||||||||||||
Monoisotopic Molecular Weight: | 4301.837534177 | |||||||||||||||||||||||||||||||||||||||||||||
InChI Key: | IOAOXSQGQQYOQU-WSFSDJJVSA-E | |||||||||||||||||||||||||||||||||||||||||||||
InChI: | InChI=1S/C181H323N3O103P4/c1-8-14-20-26-32-38-39-45-51-57-63-69-116(206)259-95(67-61-55-49-43-36-30-24-18-12-5)73-118(208)267-157-120(184-114(204)72-94(66-60-54-48-42-35-29-23-17-11-4)258-115(205)68-62-56-50-44-37-31-25-19-13-6)164(253-88-110-127(215)156(266-117(207)71-93(194)65-59-53-47-41-34-28-22-16-10-3)119(165(262-110)286-290(246,247)248)183-113(203)70-92(193)64-58-52-46-40-33-27-21-15-9-2)265-112(155(157)285-291(249,250)287-169-137(225)122(210)96(182)85-251-169)90-256-179(176(234)235)75-105(279-181(178(238)239)76-106(278-180(177(236)237)74-97(195)123(211)148(280-180)100(198)79-187)154(152(282-181)103(201)82-190)272-170-141(229)129(217)121(209)91(7)257-170)153(151(281-179)102(200)81-189)273-173-144(232)159(162(283-288(240,241)242)149(270-173)101(199)80-188)276-174-145(233)160(163(284-289(243,244)245)150(271-174)104(202)86-252-167-139(227)132(220)135(223)146(268-167)98(196)77-185)275-172-143(231)158(128(216)111(264-172)89-254-166-138(226)130(218)124(212)107(83-191)260-166)274-175-161(134(222)125(213)108(84-192)261-175)277-171-142(230)131(219)126(214)109(263-171)87-255-168-140(228)133(221)136(224)147(269-168)99(197)78-186/h91-112,119-175,185-202,209-233H,8-90,182H2,1-7H3,(H,183,203)(H,184,204)(H,234,235)(H,236,237)(H,238,239)(H,249,250)(H2,240,241,242)(H2,243,244,245)(H2,246,247,248)/p-9/t91?,92-,93-,94-,95-,96?,97?,98?,99?,100?,101?,102?,103?,104?,105?,106?,107?,108?,109?,110-,111?,112?,119-,120-,121?,122?,123?,124?,125?,126?,127-,128?,129?,130?,131?,132?,133?,134?,135?,136?,137?,138?,139?,140?,141?,142?,143?,144?,145?,146?,147?,148?,149?,150?,151?,152?,153?,154?,155-,156-,157-,158?,159?,160?,161?,162?,163?,164-,165?,166?,167?,168?,169?,170?,171?,172?,173?,174?,175?,179?,180?,181?/m1/s1 | |||||||||||||||||||||||||||||||||||||||||||||
CAS number: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
IUPAC Name: | 2-{[(3S,4R,5R,6R)-3-({[(5-amino-3,4-dihydroxyoxan-2-yl)oxy](hydroxy)phosphoryl}oxy)-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-[(2-carboxylato-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-6-(1,2-dihydroxyethyl)-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl)-4-({4-[(3-{[6-({[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl}oxy)-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}oxane-2-carboxylate | |||||||||||||||||||||||||||||||||||||||||||||
Traditional IUPAC Name: | 2-{[(3S,4R,5R,6R)-3-{[(5-amino-3,4-dihydroxyoxan-2-yl)oxy(hydroxy)phosphoryl]oxy}-5-{[(3R)-3-(dodecanoyloxy)-1-oxidotetradecylidene]amino}-6-{[(2R,3S,4R,5R)-3-hydroxy-5-{[(3R)-3-hydroxy-1-oxidotetradecylidene]amino}-4-{[(3R)-3-hydroxytetradecanoyl]oxy}-6-(phosphonooxy)oxan-2-yl]methoxy}-4-{[(3R)-3-(tetradecanoyloxy)tetradecanoyl]oxy}oxan-2-yl]methoxy}-4-[(2-carboxylato-4-{[2-carboxylato-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxan-2-yl]oxy}-6-(1,2-dihydroxyethyl)-5-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl)oxy]-6-(1,2-dihydroxyethyl)-5-{[6-(1,2-dihydroxyethyl)-4-{[6-(2-{[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-1-hydroxyethyl)-4-({4-[(3-{[6-({[6-(1,2-dihydroxyethyl)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-3,5-dihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl}oxy)-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}-3-hydroxy-5-(phosphonatooxy)oxan-2-yl]oxy}oxane-2-carboxylate | |||||||||||||||||||||||||||||||||||||||||||||
SMILES: | [H][C@@](O)(CCCCCCCCCCC)CC(=O)O[C@@]1([H])[C@]([H])(O)[C@@]([H])(CO[C@]2([H])OC([H])(COC3(CC([H])(OC4(CC([H])(OC5(CC([H])(O)C([H])(O)C([H])(O5)C([H])(O)CO)C([O-])=O)C([H])(OC5([H])OC([H])(C)C([H])(O)C([H])(O)C5([H])O)C([H])(O4)C([H])(O)CO)C([O-])=O)C([H])(OC4([H])OC([H])(C([H])(O)CO)C([H])(OP([O-])([O-])=O)C([H])(OC5([H])OC([H])(C([H])(O)COC6([H])OC([H])(C([H])(O)CO)C([H])(O)C([H])(O)C6([H])O)C([H])(OP([O-])([O-])=O)C([H])(OC6([H])OC([H])(COC7([H])OC([H])(CO)C([H])(O)C([H])(O)C7([H])O)C([H])(O)C([H])(OC7([H])OC([H])(CO)C([H])(O)C([H])(O)C7([H])OC7([H])OC([H])(COC8([H])OC([H])(C([H])(O)CO)C([H])(O)C([H])(O)C8([H])O)C([H])(O)C([H])(O)C7([H])O)C6([H])O)C5([H])O)C4([H])O)C([H])(O3)C([H])(O)CO)C([O-])=O)[C@@]([H])(OP(O)(=O)OC3([H])OCC([H])(N)C([H])(O)C3([H])O)[C@]([H])(OC(=O)C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCCCC)[C@@]2([H])N=C([O-])C[C@@]([H])(CCCCCCCCCCC)OC(=O)CCCCCCCCCCC)OC([H])(OP(O)(O)=O)[C@]1([H])N=C([O-])C[C@]([H])(O)CCCCCCCCCCC | |||||||||||||||||||||||||||||||||||||||||||||
Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||
Taxonomy Description | This compound belongs to the class of organic compounds known as polysaccharides. These are compounds containing more than ten saccharide units. | |||||||||||||||||||||||||||||||||||||||||||||
Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||
Super Class | Organic Polymers | |||||||||||||||||||||||||||||||||||||||||||||
Class | Polysaccharides | |||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Polysaccharides | |||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents |
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Substituents |
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Molecular Framework | Aliphatic heteromonocyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||
External Descriptors | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Charge: | -8 | |||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||
Cellular Locations: | Cytoplasm | |||||||||||||||||||||||||||||||||||||||||||||
Reactions: | Adenosine triphosphate + Water + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A > ADP + Hydrogen ion + Phosphate + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A Adenosine triphosphate + Water + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A > ADP + Hydrogen ion + Phosphate + 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A core oligosaccharide lipid A + undecaprenyl phosphate-4-amino-4-deoxy-L-arabinose > 4-Amino-4-deoxy-L-arabinose modified core oligosaccharide lipid A + Undecaprenyl phosphate | |||||||||||||||||||||||||||||||||||||||||||||
Pathways: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Spectra | ||||||||||||||||||||||||||||||||||||||||||||||
Spectra: | ||||||||||||||||||||||||||||||||||||||||||||||
References | ||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||
Links | ||||||||||||||||||||||||||||||||||||||||||||||
External Links: |
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Enzymes
- General function:
- Involved in transferase activity, transferring pentosyl groups
- Specific function:
- Catalyzes the transfer of the L-Ara4N moiety of the glycolipid undecaprenyl phosphate-alpha-L-Ara4N to lipid A. The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
- Gene Name:
- arnT
- Locus Tag:
- PA3556
- Molecular weight:
- 61.7 kDa
Reactions
4-amino-4-deoxy-alpha-L-arabinopyranosyl di-trans,octa-cis-undecaprenyl phosphate + lipid IV(A) = lipid II(A) + di-trans,octa-cis-undecaprenyl phosphate. |
- General function:
- Involved in lipopolysaccharide transport
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptG
- Locus Tag:
- PA3827
- Molecular weight:
- 39.2 kDa
- General function:
- Involved in lipopolysaccharide-transporting ATPase acti
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptF
- Locus Tag:
- PA3828
- Molecular weight:
- 41.3 kDa
- General function:
- Involved in nucleotide binding
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. Probably responsible for energy coupling to the transport system
- Gene Name:
- lptB
- Locus Tag:
- PA4461
- Molecular weight:
- 26.5 kDa
- General function:
- Involved in lipopolysaccharide transmembrane transporter activity
- Specific function:
- Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptC
- Locus Tag:
- PA4459
- Molecular weight:
- 21.4 kDa
- General function:
- Involved in lipopolysaccharide binding
- Specific function:
- Required for the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane. May act as a chaperone that facilitates LPS transfer across the aquaeous environment of the periplasm. Interacts specifically with the lipid A domain of LPS
- Gene Name:
- lptA
- Locus Tag:
- PA0005
- Molecular weight:
- 28.7 kDa
Transporters
- General function:
- Involved in lipopolysaccharide transport
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptG
- Locus Tag:
- PA3827
- Molecular weight:
- 39.2 kDa
- General function:
- Involved in lipopolysaccharide-transporting ATPase acti
- Specific function:
- Part of the ABC transporter complex lptBFG involved in the translocation of lipopolysaccharide (LPS) from the inner membrane to the outer membrane
- Gene Name:
- lptF
- Locus Tag:
- PA3828
- Molecular weight:
- 41.3 kDa