105974-69-4

Basic information

• Product Name: N~3~-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-N-(2-sulfanylethyl)-beta-alaninamide
• Synonyms: 2226-71-3
• CAS NO: 105974-69-4
• Molecular Formula: C₁₁H₂₃N₂O₇PS
• Molecular Weight: 358.3483
• Mol File: 105974-69-4.mol
• Article Data: 4

Chemical Properties

• Density: 1.381g/cm³
• Refractive Index: 1.539
• CAS DataBase Reference: N~3~-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-N-(2-sulfanylethyl)-beta-alaninamide(CAS DataBase Reference)
• NIST Chemistry Reference: N~3~-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-N-(2-sulfanylethyl)-beta-alaninamide(105974-69-4)
• EPA Substance Registry System: N~3~-[(2R)-2-hydroxy-3,3-dimethyl-4-(phosphonooxy)butanoyl]-N-(2-sulfanylethyl)-beta-alaninamide(105974-69-4)

Safety Data

• Hazardous Substances Data: 105974-69-4(Hazardous Substances Data)

Upstream product

• 138148-35-3 D-pantethine 
• 95871-51-5 S-Benzyl-2'-O-benzyl-pantethein 
• 599-04-2 (R)-Pantolacton 
• 55512-69-1 pantetheine 
• 60-23-1 Cysteamine 

Downstream Products

• 3633-59-8 3′-dephospho-coenzyme A 

Relevant articles and documents

An Efficient Chemoenzymatic Synthesis of Coenzyme A and Its Disulfide

We have developed a chemoenzymatic route to coenzyme A (CoASH) and its disulfide that is amenable to gram-scale synthesis using standard laboratory equipment. By synthesizing the symmetrical disulfide of pantetheine (pantethine), we avoided the need to mask the reactive sulfhydryl and also prevented sulfur oxidation byproducts. No chromatography is required in our synthetic route to pantethine, which facilitates scale-up. Furthermore, we discovered that all three enzymes of the CoASH salvage pathway (pantetheine kinase, phosphopantetheine adenyltransferase, and dephospho-coenzyme A kinase) accept the disulfide of the natural substrates and functionalize both ends of the molecules. This yields CoA disulfide as the product of the enzymatic cascade, a much more stable form of the cofactor. Free CoASH can be prepared by in situ S-S reduction.

Investigations on pantothenic acid and its related compounds. IV. Chemical studies. 3. Syntheses of D-pantetheine 4'-phosphate and N-D-pantothenoyl-L-cysteine 4'-phosphate.

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