16201-54-0

Upstream product

• 4870-65-9 2-bromophenylacetic acid 
• 4695-09-4 α-mercaptophenylacetic acid 
• 16201-51-7 (R)-2-mercapto-3-phenylacetic acid (R-thiomandelic acid) 

Downstream Products

• 103-82-2 phenylacetic acid 
• 103499-60-1 (S)-methyl 2-mercapto-2-phenylacetate 
• 53256-03-4 (S)-((S)-Methoxycarbonyl-phenyl-methyldisulfanyl)-phenyl-acetic acid methyl ester 
• 611-73-4 Benzoylformic acid 
• 4695-09-4 α-mercaptophenylacetic acid 
• 65-85-0 benzoic acid 

Relevant academic research and scientific papers

Thiol-Containing Metallo-β-Lactamase Inhibitors Resensitize Resistant Gram-Negative Bacteria to Meropenem

The prevalence of infections caused by metallo-β-lactamase (MBL) expressing Gram-negative bacteria has grown at an alarming rate in recent years. Despite the fact that MBLs can deactivate virtually all β-lactam antibiotics, there are as of yet no approved

Combining a Clostridial Enzyme Exhibiting Unusual Active Site Plasticity with a Remarkably Facile Sigmatropic Rearrangement: Rapid, Stereocontrolled Entry into Densely Functionalized Fluorinated Phosphonates for Chemical Biology

Described is an efficient stereocontrolled route into valuable, densely functionalized fluorinated phosphonates that takes advantage of (i) a Clostridial enzyme to set the absolute stereochemistry and (ii) a new [3,3]-sigmatropic rearrangement of the thiono-Claisen variety that is among the fastest sigmatropic rearrangements yet reported. Here, a pronounced rate enhancement is achieved by distal fluorination. This rearrangement is completely stereoretentive, parlaying the enzymatically established β-C-O stereochemistry in the substrate into the δ-C-S stereochemistry in the product. The final products are of interest to chemical biology, with a platform for Zn-aminopeptidase A inhibitors being constructed here. The enzyme, Clostridium acetobutylicum (CaADH), recently expressed by our group, reduces a spectrum of γ,δ-unsaturated β-keto-α,α-difluorophosphonate esters (93-99% ee; 10 examples). The resultant β-hydroxy-α,α-difluorophosphonates possess the L -stereochemistry, opposite to that previously observed for the CaADH-reduction of ω-keto carboxylate esters ( D ), indicating an unusual active site plasticity. For the thiono-Claisen rearrangement, a notable structure-reactivity relationship is observed. Measured rate constants vary by over 3 orders of magnitude, depending upon thiono-ester structure. Temperature-dependent kinetics reveal an unusually favorable entropy of activation (ΔS? = 14.5 ± 0.6 e.u.). Most notably, a 400-fold rate enhancement is seen upon fluorination of the distal arene ring, arising from favorable enthalpic (ΔΔH? = -2.3 kcal/mol) and entropic (ΔΔS? = 4 e.u., i.e. 1.2 kcal/mol at rt) contributions. The unusual active site plasticity seen here is expected to drive structural biology studies on CaADH, while the exceptionally facile sigmatropic rearrangement is expected to drive computational studies to elucidate its underlying entropic and enthalpic basis. (Chemical Presented).

Chiroptical Properties of 2,2'-Dithio- and 2,2'-Diselenobisacetic Acids

Circular dichroism (CD) studies of 2,2'-dithiobisacetic acids substituted with alkyl or phenyl groups and their diselenide analogues show that considerable interaction occurs between the disulfide (or diselenide) chromophore and the carboxyl or phenyl groups, giving rise to intense Cotton effects (CE's) which dominate the near UV region of CD spectrum.In contrast, when the disulfide and carboxyl chromophores are separated by two carbon atoms, each chromophore gives a separate CE of normal intensity at the expected wavelength with no evidence of interaction between them.