925451-46-3

Upstream product

• 2393-23-9 4-methoxy-benzylamine 
• 106018-85-3 2-trimethylsilanyl-ethanesulfonyl chloride 
• 925451-36-1 N-(2'-trimethylsilyl)ethanesulfonyl-N-(4''-chlorobutyl)-4-methoxybenzylamine 
• 925451-33-8 N-(2'-trimethylsilyl)ethanesulfonyl-4-methoxybenzylamine 
• 925451-40-7 (1R,2S)-trans-2-[2'-(β-naphthyl)-2'-propyl]cyclohexyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-vinyllysinate 
• 925451-44-1 (1R,2S)-trans-2-[2'-(β-naphthyl)-2'-propyl]cyclohexyl N^α-benzoyl-N^ε-4''-methoxybenzyl-L-α-vinyllysinate 
• 925451-38-3 N-(2'-trimethylsilyl)ethanesulfonyl-N-4''-iodobutyl-4-methoxybenzylamine 

Downstream Products

• 925451-52-1 methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'E-benzenesulfonyl-2'-fluoro)vinyllysinate 
• 925451-54-3 methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-N^ε-4'''-methoxybenzyl-L-α-(2'Z-fluoro)vinyllysinate 
• 925451-50-9 methyl N^α-benzoyl-N^ε-(2'-trimethylsilyl)ethanesulfonyl-N^ε-4''-methoxybenzyl-L-α-vinyllysinate 
• 925451-51-0 methyl N^α-benzoyl-N^ε-(2'-trimethylsilyl)ethanesulfonyl-N^ε-4''-methoxybenzyl-L-α-formyllysinate 
• 925451-55-4 methyl N^α-benzoyl-N^ε-(2''-trimethylsilyl)ethanesulfonyl-L-α-(2'Z-fluorovinyl)lysinate 
• 925451-49-6 N^α-benzoyl-N^ε-(2'-trimethylsilyl)ethanesulfonyl-N^ε-4''-methoxybenzyl-L-α-vinyllysine 

Relevant academic research and scientific papers

Examination of the new α-(2′Z-fluoro)vinyl trigger with lysine decarboxylase: The absolute stereochemistry dictates the reaction course

The first examination of a terminal α-fluorovinyl trigger in an amino acid decarboxylase active site is reported. To investigate the enantiospecificity of inactivation with this new AADC trigger, an enantioselective synthesis of l-α-(2′Z-fluoro)vinyllysine and its d-antipode has been developed. Control of stereochemistry is achieved through introduction of the amino acid side chain via alkylation of a chiral vinylglycine-derived dienolate. Facial selectivity is conferred by a trans-2′(β-naphthyl)-2′-propylcyclohexyl ester auxiliary, available in both antipodal forms (Comins protocol). The alkylation employs a new electrophile, N-p-methoxybenzyl-N-(2′-trimethylsilylethanesulfonyl)-4-iodobutylamine, for convergent installation of the lysine side chain. Vinyl to 2′-fluorovinyl interconversion then provides l- and d-α-(2′Z-fluoro)vinyllysine in 97-99% ee, as demonstrated by chiral HPLC. Both time-dependent enzyme kinetics and 19F NMR reveal striking differences in the behavior of these two antipodes in the lysine decarboxylase active site. The l-antipode displays time dependent inactivation (t1/2 = 3 ± 1 min; KI = 86 ± 22 μM), whereas the d-antipode behaves as a substrate, being completely turned over to α-(2′Z-fluoro)vinylcadaverine. Titration of LDC with varying amounts of l-α-(2′Z-fluoro)vinyllysine provides an estimate of 20 ± 3 for the partition ratio for this antipode. 19F NMR provides a more detailed account of the inactivation with the l-antipode, revealing that 1 in 3.4 turnovers of this mechanism-based inhibitor results in errant protonation (required by design), with 1 in 5 errant protonation events leading to LDC inactivation. This gives an overall partition ratio of 16 ± 2. Fluoride-selective electrode measurements are in agreement with 19F NMR estimates of [fluoride] released. Copyright