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Identification |
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YMDB ID | YMDB00202 |
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Name | Guanosine diphosphate mannose |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Guanosine diphosphate mannose, also known as gdpmannose or GDP-alpha-D-mannose, belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. Guanosine diphosphate mannose is a strong basic compound (based on its pKa). Guanosine diphosphate mannose exists in all living species, ranging from bacteria to humans. Within yeast, guanosine diphosphate mannose participates in a number of enzymatic reactions. In particular, (N-acetylglucosaminyl)2-diphosphodolichol and guanosine diphosphate mannose can be converted into mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol; which is mediated by the enzyme chitobiosyldiphosphodolichol beta-mannosyltransferase. In addition, mannosyl-(N-acetylglucosaminyl)2-diphosphodolichol and guanosine diphosphate mannose can be converted into (mannosyl)2-(N-acetylglucosaminyl)2-diphosphodolichol; which is catalyzed by the enzyme Alpha-1,3/1,6-mannosyltransferase ALG2. In yeast, guanosine diphosphate mannose is involved in the metabolic pathway called n-glycan biosynthesis pathway. |
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Structure | |
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Synonyms | - GDP mannose
- GDP-D-mannose
- GDP-glucose
- GDP-mannose
- Guanosine Diphosphate Mannose
- Guanosine diphosphomannose
- Guanosine pyrophosphate mannose
- GDPmannose
- Guanosine 5'-(trihydrogen diphosphate), mono-alpha-D-mannopyranosyl ester
- GDP-alpha-D-Mannose
- Guanosine 5'-(trihydrogen diphosphate), mono-a-D-mannopyranosyl ester
- Guanosine 5'-(trihydrogen diphosphate), mono-α-D-mannopyranosyl ester
- Guanosine 5'-(trihydrogen diphosphoric acid), mono-a-D-mannopyranosyl ester
- Guanosine 5'-(trihydrogen diphosphoric acid), mono-alpha-D-mannopyranosyl ester
- Guanosine 5'-(trihydrogen diphosphoric acid), mono-α-D-mannopyranosyl ester
- Guanosine pyrophosphoric acid mannose
- GDP-a-D-Mannose
- GDP-Α-D-mannose
- Guanosine diphosphoric acid mannose
- Pyrophosphate mannose, guanosine
- Diphosphomannose, guanosine
- Mannose, guanosine diphosphate
- Diphosphate mannose, guanosine
- Mannose, guanosine pyrophosphate
- Mannose, GDP
- Guanosine 5'-(trihydrogen diphosphate) p'-mannosyl ester
- Guanosine 5'-(trihydrogen pyrophosphate) mono-D-mannosyl ester
- Guanosine 5'-(trihydrogen pyrophosphate) monomannopyranosyl ester
- Guanosine 5'-(trihydrogen pyrophosphate) monomannosyl ester
- Guanosine 5'-diphosphate D-mannose
- Guanosine 5'-pyrophosphate D-mannosyl ester
- Guanosine 5'-pyrophosphate alpha-D-mannosyl ester
- Guanosine 5'-pyrophosphate α-D-mannosyl ester
- Guanosine 5’-(trihydrogen diphosphate) p’-mannosyl ester
- Guanosine 5’-(trihydrogen pyrophosphate) mono-D-mannosyl ester
- Guanosine 5’-(trihydrogen pyrophosphate) monomannopyranosyl ester
- Guanosine 5’-(trihydrogen pyrophosphate) monomannosyl ester
- Guanosine 5’-diphosphate D-mannose
- Guanosine 5’-pyrophosphate D-mannosyl ester
- Guanosine 5’-pyrophosphate α-D-mannosyl ester
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CAS number | 3123-67-9 |
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Weight | Average: 605.3411 Monoisotopic: 605.077152801 |
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InChI Key | MVMSCBBUIHUTGJ-GDJBGNAASA-N |
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InChI | InChI=1S/C16H25N5O16P2/c17-16-19-12-6(13(28)20-16)18-3-21(12)14-10(26)8(24)5(34-14)2-33-38(29,30)37-39(31,32)36-15-11(27)9(25)7(23)4(1-22)35-15/h3-5,7-11,14-15,22-27H,1-2H2,(H,29,30)(H,31,32)(H3,17,19,20,28)/t4-,5-,7-,8-,9+,10-,11+,14-,15-/m1/s1 |
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IUPAC Name | [({[(2R,3S,4R,5R)-5-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid |
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Traditional IUPAC Name | guanosine diphosphomannose |
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Chemical Formula | C16H25N5O16P2 |
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SMILES | [H]OC([H])([H])[C@@]1([H])O[C@]([H])(OP(=O)(O[H])OP(=O)(O[H])OC([H])([H])[C@@]2([H])O[C@@]([H])(N3C([H])=NC4=C3N=C(N([H])[H])N([H])C4=O)[C@]([H])(O[H])[C@]2([H])O[H])[C@@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as purine nucleotide sugars. These are purine nucleotides bound to a saccharide derivative through the terminal phosphate group. |
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Kingdom | Organic compounds |
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Super Class | Nucleosides, nucleotides, and analogues |
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Class | Purine nucleotides |
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Sub Class | Purine nucleotide sugars |
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Direct Parent | Purine nucleotide sugars |
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Alternative Parents | |
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Substituents | - Purine nucleotide sugar
- Purine ribonucleoside diphosphate
- Purine ribonucleoside monophosphate
- Pentose phosphate
- Pentose-5-phosphate
- Glycosyl compound
- N-glycosyl compound
- Monosaccharide phosphate
- Organic pyrophosphate
- Imidazopyrimidine
- Purine
- Hydroxypyrimidine
- Monoalkyl phosphate
- Monosaccharide
- N-substituted imidazole
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Alkyl phosphate
- Pyrimidine
- Heteroaromatic compound
- Tetrahydrofuran
- Imidazole
- Azole
- Secondary alcohol
- Polyol
- Oxacycle
- Organoheterocyclic compound
- Azacycle
- Organic oxygen compound
- Alcohol
- Organic oxide
- Primary alcohol
- Hydrocarbon derivative
- Organonitrogen compound
- Organooxygen compound
- Organic nitrogen compound
- Organopnictogen compound
- Aromatic heteropolycyclic compound
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Molecular Framework | Aromatic heteropolycyclic compounds |
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External Descriptors | |
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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 | Amino sugar and nucleotide sugar metabolism | ec00520 | | Fructose and mannose metabolism | ec00051 | | N-Glycan biosynthesis | ec00510 | |
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SMPDB Reactions |
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KEGG Reactions | |
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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 GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-05bu-5842490000-d73f755e03b8ad234b29 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-01r6-7882509000-02adbc06a0f79e803d88 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_8) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_9) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_1_10) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_4) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_5) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_6) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_7) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_8) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_9) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_10) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_11) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_12) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_13) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (TMS_2_14) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 32V, positive | splash10-0a4i-0000209000-fa2b35ba4f2fbdff74a3 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF 32V, negative | splash10-0udi-3401309000-93213e14894fde4ba5c2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0001309000-586a7f020650fe518e5f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-0900000000-bba5489b865ff8d5ba78 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0100900000-d5b51af9c9e096503197 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900400000-3410bfae1c82b5e08999 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-00b9-9434300000-661dad8f3e9cd9b10a38 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0000009000-c84788b57e1d68c3a299 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0910510000-30a5518df6f0f53ad7b7 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0910000000-48aef418f3aa94cc35f8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udi-1900000000-438261daf883fac47d6c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-1901325000-e5d0bcd5db4a59b606f8 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-1901100000-a8c00836fd0ca5a71ad1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0pdl-3900000000-358726d071759c859d9e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0000009000-3f663b5fce4f431e1e25 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-4701986000-bb5e3a66be23d7de55e6 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05i0-3911810000-ee275d8a12bcf1e5065c | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0udi-0900002000-37d2f661727ecc1c915a | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0udi-0900001000-de8f3c7c7e6a620f0e90 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0udr-2930000000-7a0fc600f843201b86c4 | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | 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
- Romero, P. A., Lussier, M., Sdicu, A. M., Bussey, H., Herscovics, A. (1997). "Ktr1p is an alpha-1,2-mannosyltransferase of Saccharomyces cerevisiae. Comparison of the enzymic properties of soluble recombinant Ktr1p and Kre2p/Mnt1p produced in Pichia pastoris." Biochem J 321 ( Pt 2):289-295.9020857
- Huh, W. K., Falvo, J. V., Gerke, L. C., Carroll, A. S., Howson, R. W., Weissman, J. S., O'Shea, E. K. (2003). "Global analysis of protein localization in budding yeast." Nature 425:686-691.14562095
- Lobsanov, Y. D., Romero, P. A., Sleno, B., Yu, B., Yip, P., Herscovics, A., Howell, P. L. (2004). "Structure of Kre2p/Mnt1p: a yeast alpha1,2-mannosyltransferase involved in mannoprotein biosynthesis." J Biol Chem 279:17921-17931.14752117
- Funato, K., Vallee, B., Riezman, H. (2002). "Biosynthesis and trafficking of sphingolipids in the yeast Saccharomyces cerevisiae." Biochemistry 41:15105-15114.12484746
- Lussier, M., Sdicu, A. M., Camirand, A., Bussey, H. (1996). "Functional characterization of the YUR1, KTR1, and KTR2 genes as members of the yeast KRE2/MNT1 mannosyltransferase gene family." J Biol Chem 271:11001-11008.8631921
- Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
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Synthesis Reference: | Huang, Gang-Liang; Liu, Xiang; Zhang, Hou-Cheng; Wang, Peng-George. A facile two-step chemo-enzymatic synthesis of GDP-mannose. Letters in Organic Chemistry (2006), 3(9), 668-669. |
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