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CAS 18186-48-6

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GDP-4-keto-6-deoxy-D-mannose

Description:
GDP-4-keto-6-deoxy-D-mannose, with the CAS number 18186-48-6, is a nucleotide sugar that plays a crucial role in the biosynthesis of polysaccharides and glycoconjugates. It is a derivative of GDP-mannose, where the hydroxyl group at the 4-position is replaced by a keto group, and the 6-position is deoxygenated. This compound is involved in various biochemical pathways, particularly in the synthesis of glycoproteins and glycolipids, which are essential for cell signaling and structural integrity. GDP-4-keto-6-deoxy-D-mannose is typically characterized by its molecular structure, which includes a guanosine diphosphate moiety linked to a modified sugar. Its reactivity is influenced by the presence of the keto group, which can participate in enzymatic reactions. The compound is of interest in both biochemical research and potential therapeutic applications, particularly in understanding glycosylation processes and developing inhibitors for related pathways. As with many nucleotide sugars, it is generally soluble in water and may be sensitive to hydrolysis under certain conditions.
Formula:C16H23N5O15P2
InChI:InChI=1S/C16H23N5O15P2/c1-4-7(22)9(24)11(26)15(33-4)35-38(30,31)36-37(28,29)32-2-5-8(23)10(25)14(34-5)21-3-18-6-12(21)19-16(17)20-13(6)27/h3-5,8-11,14-15,23-26H,2H2,1H3,(H,28,29)(H,30,31)(H3,17,19,20,27)/t4-,5-,8-,9+,10-,11+,14-,15-/m1/s1
InChI key:InChIKey=PNHLMHWWFOPQLK-BKUUWRAGSA-N
SMILES:O[C@H]1[C@H](N2C3=C(N=C2)C(=O)N=C(N)N3)O[C@H](COP(OP(O[C@@H]4[C@@H](O)[C@@H](O)C(=O)[C@@H](C)O4)(=O)O)(=O)O)[C@H]1O
Synonyms:
  • Guanosine 5′-pyrophosphate, ester with 4-keto-α-D-rhamnopyranose
  • GDP-4-keto-6-deoxy-D-mannose
  • GDP-4-keto-6-deoxymannose
  • Guanosine 5′-(trihydrogen pyrophosphate), mono(6-deoxy-α-D-lyxo-hexopyranos-4-ulosyl) ester
  • GDP-4-Dehydro-6-deoxy-D-mannose
  • Guanosine 5′-diphosphate 4-keto-6-deoxy-D-mannose
  • Guanosine 5′-(trihydrogen diphosphate), P′-(6-deoxy-α-D-lyxo-hexopyranos-4-ulos-1-yl) ester
  • [(2R,3S,4R,5R)-5-(2-amino-6-oxo-3,6-dihydro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3S,4R,6R)-3,4-dihydroxy-6-methyl-5-oxotetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)
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