Identification |
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YMDB ID | YMDB00937 |
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Name | dolichyl D-mannosyl phosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Dolichyl D-mannosyl phosphate is involved in dolichyl-diphosphooligosaccharide biosynthesis (N-linked glycosylation) pathway. N-linked glycosylation is an important process found in eukaryotes and archaea, and very rarely in bacteria. During this process certain oligosaccharides are attached to an asparagine residue in the polypeptide chain of the target protein. [Biocyc MANNOSYL-CHITO-DOLICHOL-BIOSYNTHESIS] |
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Structure | |
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Synonyms | - Dolichyl D-mannosyl phosphate
- Dolichyl phosphate D-mannose
- Dolichyl D-mannosyl phosphoric acid
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CAS number | Not Available |
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Weight | Average: 1624.4921 Monoisotopic: 1623.29737371 |
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InChI Key | IPAOLVGASNLKMS-RABFXOQVSA-N |
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InChI | InChI=1S/C106H175O9P/c1-82(2)41-22-42-83(3)43-23-44-84(4)45-24-46-85(5)47-25-48-86(6)49-26-50-87(7)51-27-52-88(8)53-28-54-89(9)55-29-56-90(10)57-30-58-91(11)59-31-60-92(12)61-32-62-93(13)63-33-64-94(14)65-34-66-95(15)67-35-68-96(16)69-36-70-97(17)71-37-72-98(18)73-38-74-99(19)75-39-76-100(20)77-40-78-101(21)79-80-113-116(111,112)115-106-105(110)104(109)103(108)102(81-107)114-106/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,101-110H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-81H2,1-21H3,(H,111,112)/b83-43+,84-45+,85-47+,86-49+,87-51-,88-53+,89-55+,90-57+,91-59+,92-61+,93-63+,94-65+,95-67+,96-69-,97-71+,98-73+,99-75+,100-77+/t101?,102-,103-,104+,105+,106?/m1/s1 |
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IUPAC Name | {[(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,62E,66E,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-yl]oxy}({[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid |
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Traditional IUPAC Name | [(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,62E,66E,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-yl]oxy[(3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphosphinic acid |
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Chemical Formula | C106H175O9P |
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SMILES | OC[C@H]1OC(OP(O)(=O)OCCC(C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(\C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CC\C=C(/C)CCC=C(C)C)[C@@H](O)[C@@H](O)[C@@H]1O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as dolichyl monophosphates. These are polyprenyl compounds consisting of a monophosphate group substituted by a dolichyl moiety. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Prenol lipids |
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Sub Class | Polyprenols |
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Direct Parent | Dolichyl monophosphates |
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Alternative Parents | |
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Substituents | - Polyterpenoid
- Polyprenyl monophosphate
- Dolichyl monophosphate
- Hexose monosaccharide
- Monosaccharide phosphate
- Dialkyl phosphate
- Alkyl phosphate
- Phosphoric acid ester
- Oxane
- Organic phosphoric acid derivative
- Monosaccharide
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Solid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | |
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SMPDB Reactions | Not Available |
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KEGG Reactions | 6-O-{alpha-D-mannosyl-(1->6)-2-O-[(2-aminoethyl)phosphoryl]-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl}-O-acyl-1-phosphatidyl-1D-myo-inositol
+
dolichyl D-mannosyl phosphate
↔
6-O-{alpha-D-mannosyl-(1->2)-alpha-D-mannosyl-(1->6)-2-O-[(2-aminoethyl)phosphoryl]-alpha-D-mannosyl-(1->4)-alpha-D-glucosaminyl}-O-acyl-1-phosphatidyl-1D-myo-inositol
| protein
+
dolichyl D-mannosyl phosphate
↔
conjugated protein
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Concentrations |
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Intracellular Concentrations | Not Available |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-2530509000-e5f9fef0171eb1f7d2db | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9031101000-bf96349fd299766d8cc4 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-88f52928fa1d1bc675fd | JSpectraViewer | MS | Mass Spectrum (Electron Ionization) | Not Available | JSpectraViewer |
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References |
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References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Banerjee, D. K., Carrasquillo, E. A., Hughey, P., Schutzbach, J. S., Martinez, J. A., Baksi, K. (2005). "In vitro phosphorylation by cAMP-dependent protein kinase up-regulates recombinant Saccharomyces cerevisiae mannosylphosphodolichol synthase." J Biol Chem 280:4174-4181.15548536
- Lamani, E., Mewbourne, R. B., Fletcher, D. S., Maltsev, S. D., Danilov, L. L., Veselovsky, V. V., Lozanova, A. V., Grigorieva, N. Y., Pinsker, O. A., Xing, J., Forsee, W. T., Cheung, H. C., Schutzbach, J. S., Shibaev, V. N., Jedrzejas, M. J. (2006). "Structural studies and mechanism of Saccharomyces cerevisiae dolichyl-phosphate-mannose synthase: insights into the initial step of synthesis of dolichyl-phosphate-linked oligosaccharide chains in membranes of endoplasmic reticulum." Glycobiology 16:666-678.16549409
- Tettelin, H., Agostoni Carbone, M. L., Albermann, K., Albers, M., Arroyo, J., Backes, U., Barreiros, T., Bertani, I., Bjourson, A. J., Bruckner, M., Bruschi, C. V., Carignani, G., Castagnoli, L., Cerdan, E., Clemente, M. L., Coblenz, A., Coglievina, M., Coissac, E., Defoor, E., Del Bino, S., Delius, H., Delneri, D., de Wergifosse, P., Dujon, B., Kleine, K., et, a. l. .. (1997). "The nucleotide sequence of Saccharomyces cerevisiae chromosome VII." Nature 387:81-84.9169869
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Synthesis Reference: | Not Available |
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External Links: | |
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