UDP-D-Xyl

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Chemical FormulaC14H20N2O16P2

 

Molecular Weight534.26 Daltons
Monoisotopic Mass536.0444556901999 Daltons
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SMILESC3(OC(OP(OP(OC[C@@H]2([C@H]([C@H]([C@H](N1(\C=C/C(=O)NC1=O))O2)O)O))(=O)[O-])(=O)[O-])[C@H](O)[C@@H](O)[C@H](O)3)
InChIInChI=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)/p-2/t5-,6-,8+,9-,10-,11-,12-,13?/m1/s1
InChIKeyInChIKey=DQQDLYVHOTZLOR-WZNRFRBMSA-L

Description: UDP-D-Xyl (Uridine Diphosphate-D-Xylose) is a nucleotide sugar composed of uridine diphosphate (UDP) linked to D-xylose, a pentose sugar. This molecule plays a vital role in the biosynthesis of glycosaminoglycans, polysaccharides, and other glycoconjugates, particularly in plants, animals, and microorganisms.

Structure & Properties:

  • Molecular Weight (MW): Approximately 536 g/mol (depending on the specific form)
  • Chemical Formula: C14H22N2O16P2
  • Synonyms: UDP-D-Xylose
  • Functional Groups: Contains uridine diphosphate (UDP) linked to D-xylose, a sugar characterized by five carbon atoms in its backbone.

Biological Role:

  • Biosynthesis Pathway: UDP-D-Xyl is synthesized from UDP-D-glucose through the action of UDP-glucose 4-epimerase. It serves as a sugar donor in various glycosylation reactions, particularly for the synthesis of extracellular matrix components in animals and cell wall polysaccharides in plants.
  • Function: UDP-D-Xyl is a key sugar donor in the biosynthesis of glycosaminoglycans, such as heparan sulfate and chondroitin sulfate in animals. It also plays a role in the biosynthesis of hemicelluloses in plants.

Applications:

  • Glycosaminoglycan Biosynthesis: In animals, UDP-D-Xyl is essential for the formation of glycosaminoglycans, which are components of the extracellular matrix and play critical roles in cell signaling, adhesion, and tissue hydration.
  • Plant Cell Wall Biosynthesis: In plants, UDP-D-Xyl is involved in the synthesis of hemicelluloses, such as xylan, which are important for cell wall structure and integrity.

Significance in Research:

  • Extracellular Matrix Research: UDP-D-Xyl is crucial for the study of extracellular matrix biosynthesis, particularly in understanding tissue formation, repair, and the development of therapeutic interventions for connective tissue disorders.
  • Plant Biology: In plant biology, UDP-D-Xyl is important for studying the synthesis of cell wall components, which have implications for biofuel production, agriculture, and the development of crop varieties with improved structural traits.

Key Roles:

  • Glycosaminoglycan Biosynthesis: UDP-D-Xyl is the initial sugar donor in the biosynthesis of glycosaminoglycans, serving as a substrate for xylosyltransferases, which catalyze the transfer of xylose to a serine residue in the core protein of proteoglycans.
  • Hemicellulose Biosynthesis: In plants, UDP-D-Xyl contributes to the production of hemicelluloses, such as xylan, which are vital for maintaining the mechanical strength and flexibility of the cell wall.

Storage and Stability:

  • Storage: UDP-D-Xyl should be stored at -20°C in a dry, moisture-free environment to maintain its stability.
  • Stability: The compound is stable under recommended storage conditions but may degrade upon exposure to moisture, heat, or light.

Research Applications:

  • Connective Tissue Disorders: Research into UDP-D-Xyl has potential implications for understanding and treating connective tissue disorders that involve defects in glycosaminoglycan biosynthesis.
  • Bioengineering: UDP-D-Xyl is used in the engineering of plants and microorganisms to modify cell wall composition, which can lead to advances in biofuel production, crop improvement, and materials science.

Potential Impact:

  • Therapeutic Applications: UDP-D-Xyl can be targeted in therapeutic strategies aimed at modulating glycosaminoglycan biosynthesis, which has potential applications in tissue regeneration, cancer treatment, and inflammatory diseases.
  • Agricultural and Industrial Applications: In plants, manipulation of UDP-D-Xyl metabolism can lead to the development of crops with improved biomass yield and better resistance to environmental stresses, as well as innovations in the production of renewable materials.

Key Research Areas:

  • Extracellular Matrix and Proteoglycans: Understanding how UDP-D-Xyl contributes to the formation of glycosaminoglycans can provide insights into tissue development, repair, and disease mechanisms in animals.
  • Plant Cell Wall Engineering: Research on UDP-D-Xyl in plants focuses on the biosynthesis of cell wall polysaccharides, which is crucial for developing new plant-based materials and improving crop productivity.

Conclusion: UDP-D-Xyl is an essential nucleotide sugar involved in the biosynthesis of glycosaminoglycans in animals and hemicelluloses in plants. Its role in cell wall integrity, tissue repair, and various biological processes makes it a significant molecule for research in both health and agricultural sciences. The potential to manipulate UDP-D-Xyl pathways offers opportunities for therapeutic advancements and innovations in biotechnology and bioengineering

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Size

15 MG, 25 MG, 5 MG

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