55666-46-1

Basic information

• Product Name: C₂₀H₃₁NO₆S
• Synonyms: C₂₀H₃₁NO₆S
• CAS NO: 55666-46-1
• Molecular Weight: 413.535
• Mol File: 55666-46-1.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: C₂₀H₃₁NO₆S(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₀H₃₁NO₆S(55666-46-1)
• EPA Substance Registry System: C₂₀H₃₁NO₆S(55666-46-1)

Safety Data

• Hazardous Substances Data: 55666-46-1(Hazardous Substances Data)

Upstream product

• 32677-01-3 L-glutamic acid di-tert-butyl ester hydrochloride 
• 98-59-9 p-toluenesulfonyl chloride 
• 200806-94-6 2-(4-methylbenzenesulfonamido)pentanedioic acid 
• 115-11-7 isobutene 

Downstream Products

• 4816-80-2 N-tosyl-L-glutamic acid 

Relevant articles and documents

N-Substituted Glutamyl Sulfonamides as Inhibitors of Glutamate Carboxypeptidase II (GCP2)

Glutamate carboxypeptidase II (GCP2) is a membrane-bound cell-surface peptidase which is implicated in several neurological disorders and is also over-expressed in prostate tumor cells. There is a significant interest in the inhibition of GCP2 as a means of neuroprotection, while GCP2 inhibition as a method to treat prostate cancer remains a topic of further investigation. The key zinc-binding functional group of the well-characterized classes of GCP2 inhibitors (phosphonates and phosphoramidates) is tetrahedral and negatively charged at neutral pH, while glutamyl urea class of inhibitors possesses a planar and neutral zinc-binding group. This study introduces a new class of GCP2 inhibitors, N-substituted glutamyl sulfonamides, which possess a neutral tetrahedral zinc-binding motif. A library containing 15 secondary sulfonamides and 4 tertiary (N-methyl) sulfonamides was prepared and evaluated for inhibitory potency against purified GCP2 enzyme activity. While most inhibitors lacked potency at 100μm, short alkyl sulfonamides exhibited promising low micromolar potency, with the optimal inhibitor in this series being glutamyl N-(propylsulfonamide) (2g). Lastly, molecular docking was used to develop a model to formulate an explanation for the relative inhibitory potencies employed for this class of inhibitors. A small library of glutamyl sulfonamides was prepared and evaluated for in vitro potency against glutamate carboxypeptidase II (GCP2). Short alkyl sulfonamide inhibitors were the most potent, demonstrating low micromolar IC50 values.