174231-06-2

Upstream product

• 174231-05-1 (2S,5R,6S)-6-Bromo-6-((R)-1-hydroxy-ethyl)-3,3-dimethyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid 4-nitro-benzyl ester 
• 98510-71-5 4-Nitrobenzyl 6,6-dibromopenicillanate 
• 302904-78-5 C₁₇H₁₉BrN₂O₆S 

Downstream Products

• 1186219-17-9 C₂₃H₃₄N₂O₆SSi 

Relevant academic research and scientific papers

Quantification of the extent of attenuation of the rate of turnover chemistry of the TEM-1 β-lactamase by the α-1R-hydroxyethyl group in substrates

The 6α-1R-hydroxyethyl group of imipenem, a clinically used carbapenem antibacterial agent, is believed to displace the hydrolytic water from its optimal position in the active site of class A β-lactamases. This interaction renders the molecule a poor substrate for these bacterial enzymes, hence preserving the antibacterial property of the antibiotic. The extent of the contribution of the 6α-1R-hydroxyethyl group in substrates toward stabilization of the antibiotic to the hydrolytic action of class A TEM-1 β-lactamase was studied by the synthesis and evaluation of two penicillanic acid derivatives, 6α-(1R-hydroxyethyl)penicillanic acid (2) and 6β-(1R-hydroxyethyl)penicillanic acid (3). The kinetic evaluation of the enzymic hydrolysis of these two penicillanic acid derivatives indicated that the 6α-1R-hydroxyethyl group imparts as much as 104-fold to the hydrolytic stability of the β-lactam substrate. Copyright

Synthesis and biological evaluation of penem inhibitors of bacterial signal peptidase

We report the first synthesis of a 5S penem, known to bind bacterial type I signal peptidase, from the commercially available and inexpensive 6-aminopenicillanic acid. We report the first in vivo activity of the compound and use structure-activity relationship studies to begin to define the determinants of signal peptidase binding and also to begin to optimize the penem as an antibiotic.

Stereoselective reduction of α-bromopenicillanates by tributylphosphine

Diastereoselective reduction of 6-bromo-6-substituted penicillanate esters has been achieved by treatment with tributylphosphine to give 6-substituted penicillanate esters. This reaction would appear to proceed through a phosphonium β-lactam enolate speci