CAS 6815-91-4

GDP-L-galactose

Description:

GDP-L-galactose, or guanosine diphosphate L-galactose, is a nucleotide sugar that plays a crucial role in carbohydrate metabolism and biosynthesis. It is a derivative of galactose, a monosaccharide, and is involved in the synthesis of polysaccharides and glycoproteins. The compound consists of a guanosine moiety linked to two phosphate groups and a galactose sugar, which is in the L-configuration. GDP-L-galactose serves as a donor of galactose residues in various glycosylation reactions, facilitating the transfer of galactose to acceptor molecules. This process is essential for the formation of complex carbohydrates and is significant in cellular functions, including cell signaling and structural integrity. The compound is typically found in the cytoplasm of cells and is synthesized from UDP-galactose through specific enzymatic pathways. Its role in metabolic pathways highlights its importance in both plant and animal systems, particularly in the synthesis of glycoproteins and glycolipids.

Formula: C₁₆H₂₅N₅O₁₆P₂

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+/m0/s1

InChI key: InChIKey=MVMSCBBUIHUTGJ-JGQUBWHWSA-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]4O[C@@H](CO)[C@@H](O)[C@@H](O)[C@@H]4O)(=O)O)(=O)O)[C@H]1O

Synonyms:

• GDP-<span class="text-smallcaps">L</span>-galactose
• GDP-Gal
• GDP-L-galactose
• GDP-b-L-galactose
• GDP-galactose
• GDP-β-<span class="text-smallcaps">L</span>-galactose
• Guanosine 5'-(trihydrogen diphosphate), P'-L-galactopyranosyl ester
• Guanosine 5'-(trihydrogenpyrophosphate), mono-b-L-galactopyranosyl ester(8CI)
• Guanosine 5'-pyrophosphate, b-L-galactopyranosyl ester (6CI)
• Guanosine 5'-pyrophosphate, b-L-galactosyl ester
• Guanosine 5'-pyrophosphate, galactosylester
• Guanosine 5′-(trihydrogen diphosphate), P′-<span class="text-smallcaps">L</span>-galactopyranosyl ester
• Guanosine 5′-(trihydrogen diphosphate), P′-<span class="text-smallcaps">L</span>-galactosyl ester
• Guanosine 5′-(trihydrogen diphosphate), P′-β-<span class="text-smallcaps">L</span>-galactopyranosyl ester
• Guanosine 5′-(trihydrogen pyrophosphate), mono-β-<span class="text-smallcaps">L</span>-galactopyranosyl ester
• Guanosine 5′-diphosphate-<span class="text-smallcaps">L</span>-galactose
• Guanosine 5′-pyrophosphate, <span class="text-smallcaps">L</span>-galactosyl ester
• Guanosine 5′-pyrophosphate, galactosyl ester
• Guanosine 5′-pyrophosphate, β-<span class="text-smallcaps">L</span>-galactopyranosyl ester
• Guanosine 5′-pyrophosphate, β-<span class="text-smallcaps">L</span>-galactosyl ester
• Guanosine diphosphate galactose
• Guanosine diphosphogalactose
• Guanosine5'-(trihydrogen diphosphate),P'-L-galactosyl ester
• Guanosine5'-diphosphate-L-galactose
• Guanosine5'-pyrophosphate, L-galactosyl ester
• Guanosine 5′-(trihydrogen pyrophosphate), mono-β-L-galactopyranosyl ester
• Guanosine 5′-(trihydrogen diphosphate), P′-β-L-galactopyranosyl ester

GDP-L-galactose sodium salt

CAS: 6815-91-4

GDP-L-galactose is a sugar molecule that is an intermediate in the biosynthesis of ascorbate. GDP-L-galactose is synthesized from GDP-D-mannose and GDP-L-glucose by the enzyme GDP-mannose 4,6 dehydratase. The enzyme GDP-L-galactose dehydrogenase then converts GDP-L-galactose to ascorbic acid (vitamin C). Ascorbate is essential for many biological functions such as synthesis of collagen and neurotransmitters, regulation of gene expression, and protection against oxidative stress. The biosynthesis of ascorbate occurs in a light dependent reaction involving L -galactono 1,4 diphosphate synthase and UDP glucose 6 phosphate uridylyl transferase. This process is regulated by transcriptional factors such as MYB and NAC2/NAC4.

Formula: C₁₆H₂₃N₅O₁₆P₂Na₂

Purity: (Hplc-Ms) Min. 95 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 649.3 g/mol

Ref: 3D-MG01735