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Revision as of 11:01, 9 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'DrugBank_Ref', 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref') per Chem/Drugbox validation (report [[Wikipedia_talk:Wi← Previous edit Latest revision as of 12:14, 21 October 2024 edit undoMarbletan (talk | contribs)Extended confirmed users5,333 edits no longer a stub 
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{{chembox {{chembox
| verifiedrevid = 443850622 | verifiedrevid = 443851992
| ImageFile = GDP-mannose.png | ImageFile = GDP-mannose.svg
| ImageSize = | ImageSize = 250px
| IUPACName = Guanosine 5′-(α-<small>D</small>-mannopyranosyl dihydrogen diphosphate)
| IUPACName = methyl (2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl dihydrogen diphosphate | SystematicName = ''O''<sup>1</sup>-<nowiki/>{methyl} ''O''<sup>3</sup>- dihydrogen diphosphate
| OtherNames = | OtherNames =
| Section1 = {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 17372 | ChemSpiderID = 17372
| InChI = 1/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 | InChI = 1/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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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = MVMSCBBUIHUTGJ-GDJBGNAASA-N | StdInChIKey = MVMSCBBUIHUTGJ-GDJBGNAASA-N
⚫ | CASNo_Ref = {{cascite|correct|??}}
| CASNo = 3123-67-9 | CASNo = 3123-67-9
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | PubChem = 18396
| UNII = SA0B77H8CS
⚫ | ChEBI_Ref = {{ebicite|correct|EBI}}
⚫ | PubChem = 18396
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 15820 | ChEBI = 15820
| SMILES = O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC4O(n2c3NC(=N/C(=O)c3nc2)\N)(O)4O | SMILES = O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC4O(n2c3NC(=N/C(=O)c3nc2)\N)(O)4O
| MeSHName = Guanosine+Diphosphate+Mannose | MeSHName = Guanosine+Diphosphate+Mannose
}} }}
| Section2 = {{Chembox Properties |Section2={{Chembox Properties
| Formula = C<sub>16</sub>H<sub>25</sub>N<sub>5</sub>O<sub>16</sub>P<sub>2</sub> | Formula = C<sub>16</sub>H<sub>25</sub>N<sub>5</sub>O<sub>16</sub>P<sub>2</sub>
| MolarMass = 605.341 g/mol | MolarMass = 605.341 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
}} }}
| Section3 = {{Chembox Hazards |Section3={{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}
'''Guanosine diphosphate mannose''' or '''GDP-mannose''' is a ] that is a substrate for ] reactions in ]. This compound is a substrate for enzymes called ]s. '''Guanosine diphosphate mannose''' or '''GDP-mannose''' is a ] that is a substrate for ] reactions in ]. This compound is a substrate for enzymes called ]s.

Known as donor of activated mannose in all glycolytic reactions, GDP-mannose is essential in eukaryotes.<ref>{{Cite journal|last1=Stewart|first1=James|last2=Curtis|first2=Joan|last3=Spurck|first3=Timothy P.|last4=Ilg|first4=Thomas|last5=Garami|first5=Attila|last6=Baldwin|first6=Tracey|last7=Courret|first7=Nathalie|last8=McFadden|first8=Geoffrey I.|last9=Davis|first9=Antony|last10=Handman|first10=Emanuela|date=July 2005 |title=Characterisation of a Leishmania mexicana knockout lacking guanosine diphosphate-mannose pyrophosphorylase|journal=International Journal for Parasitology|language=en|volume=35|issue=8|pages=861–873|doi=10.1016/j.ijpara.2005.03.008|pmid=15936761}}</ref>

==Biosynthesis== ==Biosynthesis==
GDP-mannose is produced from ] and ] by the enzyme ].<ref name="Reeves">{{cite journal |author=Samuel G, Reeves P |title=Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly |journal=Carbohydr. Res. |volume=338 |issue=23 |pages=2503–19 |year=2003 |pmid=14670712 |doi=10.1016/j.carres.2003.07.009}}</ref> GDP-mannose is produced from ] and ] by the enzyme ] (GDP-mannose pyrophosphorylase, GDP-MP).<ref name="Reeves">{{cite journal |vauthors=Samuel G, Reeves P |title=Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly |journal=Carbohydrate Research |volume=338 |issue=23 |pages=2503–19 |year=2003 |pmid=14670712 |doi=10.1016/j.carres.2003.07.009}}</ref> This enzyme belongs to a family of nucleotidyl-transferases and is a pervasive enzyme found in bacteria, fungi, plants, and animals.<ref>{{Cite journal|last1=Pomel|first1=Sébastien|last2=Mao|first2=Wei|last3=Ha-Duong|first3=Tâp|last4=Cavé|first4=Christian|last5=Loiseau|first5=Philippe M.|date=2019-05-31|title=GDP-Mannose Pyrophosphorylase: A Biologically Validated Target for Drug Development Against Leishmaniasis|journal=Frontiers in Cellular and Infection Microbiology|volume=9|pages=186|doi=10.3389/fcimb.2019.00186|issn=2235-2988|pmc=6554559|pmid=31214516|doi-access=free}}</ref>


==References== ==References==
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] ]


{{biochem-stub}}

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Latest revision as of 12:14, 21 October 2024

Guanosine diphosphate mannose
Names
IUPAC name Guanosine 5′-(α-D-mannopyranosyl dihydrogen diphosphate)
Systematic IUPAC name O-{methyl} O- dihydrogen diphosphate
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
MeSH Guanosine+Diphosphate+Mannose
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: MVMSCBBUIHUTGJ-GDJBGNAASA-N
  • InChI=1/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/s1Key: MVMSCBBUIHUTGJ-GDJBGNAABK
SMILES
  • O=P(O1O((O)(O)1O)CO)(O)OP(=O)(O)OC4O(n2c3NC(=N/C(=O)c3nc2)\N)(O)4O
Properties
Chemical formula C16H25N5O16P2
Molar mass 605.341 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). checkY verify (what is  ?) Infobox references
Chemical compound

Guanosine diphosphate mannose or GDP-mannose is a nucleotide sugar that is a substrate for glycosyltransferase reactions in metabolism. This compound is a substrate for enzymes called mannosyltransferases.

Known as donor of activated mannose in all glycolytic reactions, GDP-mannose is essential in eukaryotes.

Biosynthesis

GDP-mannose is produced from GTP and mannose-6-phosphate by the enzyme mannose-1-phosphate guanylyltransferase (GDP-mannose pyrophosphorylase, GDP-MP). This enzyme belongs to a family of nucleotidyl-transferases and is a pervasive enzyme found in bacteria, fungi, plants, and animals.

References

  1. Stewart, James; Curtis, Joan; Spurck, Timothy P.; Ilg, Thomas; Garami, Attila; Baldwin, Tracey; Courret, Nathalie; McFadden, Geoffrey I.; Davis, Antony; Handman, Emanuela (July 2005). "Characterisation of a Leishmania mexicana knockout lacking guanosine diphosphate-mannose pyrophosphorylase". International Journal for Parasitology. 35 (8): 861–873. doi:10.1016/j.ijpara.2005.03.008. PMID 15936761.
  2. Samuel G, Reeves P (2003). "Biosynthesis of O-antigens: genes and pathways involved in nucleotide sugar precursor synthesis and O-antigen assembly". Carbohydrate Research. 338 (23): 2503–19. doi:10.1016/j.carres.2003.07.009. PMID 14670712.
  3. Pomel, Sébastien; Mao, Wei; Ha-Duong, Tâp; Cavé, Christian; Loiseau, Philippe M. (2019-05-31). "GDP-Mannose Pyrophosphorylase: A Biologically Validated Target for Drug Development Against Leishmaniasis". Frontiers in Cellular and Infection Microbiology. 9: 186. doi:10.3389/fcimb.2019.00186. ISSN 2235-2988. PMC 6554559. PMID 31214516.

See also

Types of nucleotide sugars
Categories: