83398-52-1

Basic information

• Product Name: (R)-1-fluoro-3-O-ptoluenesulfonyl-2,3-propanediol
• Synonyms: (R)-1-fluoro-3-O-ptoluenesulfonyl-2,3-propanediol
• CAS NO: 83398-52-1
• Molecular Weight: 248.275
• Mol File: 83398-52-1.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (R)-1-fluoro-3-O-ptoluenesulfonyl-2,3-propanediol(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-fluoro-3-O-ptoluenesulfonyl-2,3-propanediol(83398-52-1)
• EPA Substance Registry System: (R)-1-fluoro-3-O-ptoluenesulfonyl-2,3-propanediol(83398-52-1)

Safety Data

• Hazardous Substances Data: 83398-52-1(Hazardous Substances Data)

Upstream product

• 70987-78-9 (S)-Glycidyl tosylate 
• 32860-39-2 (2R)-3-fluoropropane-1,2-diol 
• 98-59-9 p-toluenesulfonyl chloride 

Downstream Products

• 146459-57-6 diisopropyl (R)-({[1-fluoro-3-(tosyloxy)propan-2-yl]oxy}methyl)phosphonate 
• 146459-60-1 (R)-2-acetoxymethoxy-3-fluoropropyl p-toluenesulfonate 
• 146459-59-8 (R)-1-fluoro-2-methoxymethoxypropyl p-toluenesulfonate 

Relevant articles and documents

The Role of Chirality of [18F]SMBT-1 in Imaging of Monoamine Oxidase-B

(S)-(2-Methylpyrid-5-yl)-6-[(3-[18F]fluoro-2-hydroxy)propoxy]quinoline ([18F]SMBT-1) was recently developed as a novel class of selective and reversible monoamine oxidase-B (MAO-B) tracers for in vivo imaging of reactive astrogliosis via positron emission tomography. To investigate the effect of the chirality of [18F]SMBT-1 on tracer performance, we synthesized (S)-[18F]6 ([18F]SMBT-1) and (R)-[18F]6 and compared their binding properties, pharmacokinetics, and metabolism. (S)-6 showed higher binding affinity to MAO-B and lower binding affinity to MAO-A than (R)-6, demonstrating a higher selectivity ratio (MAO-B/MAO-A). A pharmacokinetic study in mice demonstrated that both (S)-[18F]6 and (R)-[18F]6 showed sufficient initial brain uptake. However, (S)-[18F]6 was cleared significantly faster from the body. An abundant sulfoconjugate metabolite M2 was observed in plasma for (S)-[18F]6 but not for (R)-[18F]6. In vitro sulfation assays confirmed that (S)-6 was more reactive than (R)-6, consistent with the in vivo findings. Mefenamic acid, a selective sulfotransferase 1A1 (SULT1A1) inhibitor, strongly inhibited the in vitro sulfation of (S)-6 by mouse liver fractions, human liver cytosol fractions, and human recombinant SULT1A1 enzyme. Genetic polymorphisms of SULT1A1 did not affect the sulfation of (S)-6 in vitro. In conclusion, (S)-[18F]6 had a more favorable binding affinity and binding selectivity for MAO-B than (R)-[18F]6. Additionally, (S)-[18F]6 also possessed better pharmacological and metabolic properties than (R)-[18F]6. These results suggest that (S)-[18F]6 ([18F]SMBT-1) is a promising candidate for application in the imaging of MAO-B in vivo.

Selectively Deuterated and Optically Active Cyclic Ethers

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