2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate (PAMDB006334)
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| Version | 1.0 | |||||||||
| Update Date | 1/22/2018 12:54:54 PM | |||||||||
| Metabolite ID | PAMDB006334 | |||||||||
| Identification | ||||||||||
| Name: | 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate | |||||||||
| Description: | 2,3-bis((3R)-3-Hydroxymyristoyl)-alpha-D-glucosaminyl 1-phosphate is an intermediate in Lipid IVA synthesis which is essesntial for the production of LPS. Lipopolysaccharide (LPS), a major outer membrane component, is composed of three domains: Lipid A, the core, which is an oligosaccharide consisting of an inner and outer region; and a distal repeating unit known as the O-antigen. Lipid A is linked to a beta-1,6-linked glucosamine disaccharide. Attached to this is the inner core containing at least two 3-deoxy-D-manno-octulosonate (KDO) units followed by two units of heptose. The outer core region and the O-antigen are attached to one of the heptose units. For some time it was thought that the minimum structure for cell viability in Pseudomonas aeruginosa had the di-Kdo moiety, but viable mutants lacking Kdo and with the basic tetra-acyl form of lipid A, i.e. lacking the two secondary acyl groups (and termed 'lipid IVA'), have recently been produced. Indeed, lipid IVA may be the minimum structure required for the viability of Pseudomonas aeruginosa. | |||||||||
| Structure |
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| Synonyms: |
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| Chemical Formula: | C34H64NO12P | |||||||||
| Average Molecular Weight: | 709.856 | |||||||||
| Monoisotopic Molecular Weight: | 709.417710663 | |||||||||
| InChI Key: | HEHQDWUWJVPREQ-UHFFFAOYSA-L | |||||||||
| InChI: | InChI=1S/C34H66NO12P/c1-3-5-7-9-11-13-15-17-19-21-26(37)23-29(39)35-31-33(32(41)28(25-36)45-34(31)47-48(42,43)44)46-30(40)24-27(38)22-20-18-16-14-12-10-8-6-4-2/h26-28,31-34,36-38,41H,3-25H2,1-2H3,(H,35,39)(H2,42,43,44)/p-2 | |||||||||
| CAS number: | Not Available | |||||||||
| IUPAC Name: | Not Available | |||||||||
| Traditional IUPAC Name: | Not Available | |||||||||
| SMILES: | CCCCCCCCCCCC(O)CC(=O)NC1C(OP([O-])([O-])=O)OC(CO)C(O)C1OC(=O)CC(O)CCCCCCCCCCC | |||||||||
| Chemical Taxonomy | ||||||||||
| Taxonomy Description | Not Available | |||||||||
| Kingdom | Not Available | |||||||||
| Super Class | Not Available | |||||||||
| Class | Not Available | |||||||||
| Sub Class | Not Available | |||||||||
| Direct Parent | Not Available | |||||||||
| Alternative Parents | Not Available | |||||||||
| Substituents | Not Available | |||||||||
| Molecular Framework | Not Available | |||||||||
| External Descriptors | Not Available | |||||||||
| Physical Properties | ||||||||||
| State: | Not Available | |||||||||
| Charge: | Not Available | |||||||||
| Melting point: | Not Available | |||||||||
| Experimental Properties: |
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| Predicted Properties | ||||||||||
| Biological Properties | ||||||||||
| Cellular Locations: | Cytoplasm | |||||||||
| Reactions: | UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine > Uridine 5'-diphosphate + Hydrogen ion + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) | |||||||||
| SMPDB Pathways: |
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| Biological Properties | ||||||||||
| Cellular Locations: | Cytoplasm | |||||||||
| Reactions: | UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine + Water > Uridine 5'-monophosphate + Hydrogen ion + 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate 2,3-bis[(3R)-3-hydroxymyristoyl]-α-D-glucosaminyl 1-phosphate + UDP-2-N,3-O-bis[(3R)-3-hydroxytetradecanoyl]-α-D-glucosamine > Uridine 5'-diphosphate + Hydrogen ion + (2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl)-(1->6)-(2-N,3-O-bis(3-hydroxytetradecanoyl)-beta-D-glucosaminyl phosphate) | |||||||||
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| References | ||||||||||
| References: | Not Available | |||||||||
| Synthesis Reference: | Not Available | |||||||||
| Material Safety Data Sheet (MSDS) | Not Available | |||||||||
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