CAS 15839-78-8

UDP-arabinose

Description:

UDP-arabinose, or uridine diphosphate arabinose, is a nucleotide sugar that plays a crucial role in the biosynthesis of polysaccharides, particularly in the formation of plant cell wall components. It is a derivative of uridine diphosphate (UDP) and arabinose, a five-carbon sugar. UDP-arabinose serves as a glycosyl donor in various glycosylation reactions, facilitating the transfer of arabinose residues to growing polysaccharide chains. This compound is essential in the synthesis of pectin and hemicellulose, which are vital for plant structure and integrity. UDP-arabinose is typically found in the cytoplasm of plant cells and is involved in metabolic pathways that contribute to cell wall modification and expansion. Its role in plant biology makes it a subject of interest in studies related to plant development, stress responses, and bioengineering for improved crop traits. The compound is characterized by its stability under physiological conditions, although it can be sensitive to hydrolysis in the presence of certain enzymes.

Formula: C₁₄H₂₂N₂O₁₆P₂

InChI: InChI=1S/C14H22N2O16P2/c17-5-3-28-13(11(22)8(5)19)31-34(26,27)32-33(24,25)29-4-6-9(20)10(21)12(30-6)16-2-1-7(18)15-14(16)23/h1-2,5-6,8-13,17,19-22H,3-4H2,(H,24,25)(H,26,27)(H,15,18,23)/t5-,6+,8-,9+,10+,11+,12+,13+/m0/s1

InChI key: InChIKey=DQQDLYVHOTZLOR-IAZOVDBXSA-N

SMILES: O[C@H]1[C@@H](O[C@H](COP(OP(O[C@@H]2[C@H](O)[C@@H](O)[C@@H](O)CO2)(=O)O)(=O)O)[C@H]1O)N3C(=O)NC(=O)C=C3

Synonyms:

• UDP-<span class="text-smallcaps">L</span>-arabinose
• UDP-arabinose
• UDP-β-<span class="text-smallcaps">L</span>-arabinopyranose
• Uridine 5′-(trihydrogen diphosphate) mono-<span class="text-smallcaps">L</span>-arabinopyranosyl ester
• Uridine 5′-(trihydrogen diphosphate), P′-β-<span class="text-smallcaps">L</span>-arabinopyranosyl ester
• Uridine 5′-(trihydrogen pyrophosphate) mono-<span class="text-smallcaps">L</span>-arabinopyranosyl ester
• Uridine 5′-(trihydrogen pyrophosphate) mono-<span class="text-smallcaps">L</span>-arabinosyl ester
• Uridine 5′-(trihydrogen pyrophosphate), mono-β-<span class="text-smallcaps">L</span>-arabinopyranosyl ester
• Uridine 5′-diphosphate arabinoside
• Uridine 5′-pyrophosphate, β-<span class="text-smallcaps">L</span>-arabinopyranosyl ester
• Uridine 5′-pyrophosphate, β-<span class="text-smallcaps">L</span>-arabinosyl ester
• Uridine diphosphate arabinose
• Uridine diphospho-β-<span class="text-smallcaps">L</span>-arabinopyranose
• Uridine diphosphoarabinose
• [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl (2R,3R,4S,5S)-3,4,5-trihydroxytetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)
• Uridine 5′-pyrophosphate, β-L-arabinopyranosyl ester
• Uridine 5′-(trihydrogen diphosphate), P′-β-L-arabinopyranosyl ester

UDP-b-L-arabinopyranose

CAS: 15839-78-8

UDP-b-L-arabinopyranose is a nucleotide sugar that is used in the synthesis of proteins and other macromolecules. It is synthesized from uridine and d-ribulose 5-phosphate by the enzyme ribulokinase. The reaction between UDP, b-L-arabinofuranose, and ATP, catalyzed by arabinofuranosyl transferase, produces UDP-b-L-arabinopyranose. This nucleotide sugar can be converted to UDP-b-(1→4)-glucuronate by the enzyme glucuronosyltransferase. This process plays an important role in plant physiology as well as in cell wall biosynthesis. The optimal pH for this conversion is 7.5 to 8.2.

Formula: C₁₄H₂₂N₂O₁₆P₂

Purity: Min. 95%

Color and Shape: Powder

Molecular weight: 536.28 g/mol

Ref: 3D-MU07659