CAS 2627-73-8

3-Deoxy-D-arabino-heptulosonate 7-phosphate

Description:

3-Deoxy-D-arabino-heptulosonate 7-phosphate (often abbreviated as DAAHP) is a biochemical compound that plays a crucial role in the shikimic acid pathway, which is essential for the biosynthesis of aromatic amino acids in plants, fungi, and some bacteria. This compound is characterized by its phosphate group, which contributes to its solubility and reactivity in biological systems. DAAHP is a key intermediate in the synthesis of chorismate, a precursor for the production of essential metabolites such as phenylalanine, tyrosine, and tryptophan. The structure of DAAHP features a heptulose sugar backbone, which is a seven-carbon sugar, and its configuration is critical for its biological function. The compound is typically found in a phosphorylated form, which is important for its enzymatic interactions. Due to its role in metabolic pathways, DAAHP is of interest in studies related to plant biochemistry and microbial metabolism, and it may also have implications in the development of herbicides and antibiotics targeting the shikimic acid pathway.

Formula: C₇H₁₃O₁₀P

InChI: InChI=1S/C7H13O10P/c8-3(1-4(9)7(12)13)6(11)5(10)2-17-18(14,15)16/h3,5-6,8,10-11H,1-2H2,(H,12,13)(H2,14,15,16)/t3-,5-,6+/m1/s1

InChI key: InChIKey=PJWIPEXIFFQAQZ-PUFIMZNGSA-N

SMILES: [C@H]([C@@H]([C@@H](COP(=O)(O)O)O)O)(CC(C(O)=O)=O)O

Synonyms:

• D-arabino-Heptulosonic acid, 3-deoxy-, 7-phosphate
• D-arabino-2-Heptulosonic acid, 3-deoxy-, 7-(dihydrogen phosphate)
• DAHP
• D-arabino-Heptulosonic acid, 3-deoxy-, 7-(dihydrogen phosphate)
• Glucoheptonic acid, 3-deoxy-2-keto-, 7-phosphate, D-

3-Deoxy-D-arabinoheptulosonic Acid 7-Phosphate Disodium Salt

Controlled Product

CAS: 2627-73-8

Applications It stands at the beginning of the enzyme-catalyzed cascade that starts with this seven-carbon carbohydrate and ends with the aromatic amino acids phenylalanine, tyrosine, and tryptophan.
References Frost, J.W., et al.: Biochemistry, 23, 4465 (1984)

Formula: C₇H₁₁Na₂O₁₀P

Color and Shape: Neat

Molecular weight: 332.11

Ref: TR-D232050

3-Deoxy-D-arabino-heptulosonic acid 7-phosphate disodium salt

CAS: 2627-73-8

3-Deoxy-D-arabinonoheptulosonic acid 7-phosphate disodium salt is a phosphate derivative of 3-deoxy-D-arabinoheptulosonic acid (DAHP), which is an intermediate in the biosynthesis of heparin. DAHP is synthesized by the enzyme DAHP synthetase, which catalyses the conversion of D-xylose to DAHP. The enzyme can be activated by adding xylose or other sugar phosphates, and it can be inhibited by adding anthranilate or arabinose. 3-Deoxy-D-arabinonoheptulosonic acid 7-phosphate disodium salt is used as a substrate for various enzymes, including enzymes in biological samples and model systems. It was also used to study the rate constant for the polymerase chain reaction (PCR).

Formula: C₇H₁₁Na₂O₁₀P

Purity: Min. 95%

Color and Shape: Off-White Powder

Molecular weight: 332.11 g/mol

Ref: 3D-MD00561

3-Deoxy-D-arabino-heptulosonate 7-Phosphate

CAS: 2627-73-8

Formula: C₇H₁₃O₁₀P

Molecular weight: 288.14

Ref: ST-EA-CP-A333001

3-Deoxy-D-arabino-heptulosonate 7-Phosphate

CAS: 2627-73-8

Formula: C₇H₁₃O₁₀P

Molecular weight: 288.14

Ref: 4Z-A-316003