1464802-73-0

Upstream product

• 437768-95-1 (S)-N⁽¹⁾-(p-methoxybenzyl)-6-isopropylpiperazine-2,5-dione 
• 1456900-73-4 (S)-5-ethoxy-6-isopropyl-1-(4-methoxybenzyl)-1,6-dihydropyrazin-2(3H)-one 
• 3618-04-0 4-hydroxycyclohexyl carboxylic acid ethyl ester 
• 69739-34-0 t-butyldimethylsiyl triflate 
• 676560-15-9 Ethyl (cis/trans)-4-<(tert-butyldimethylsilyl)oxy>cyclohexanecarboxylate 
• 189753-93-3 (cis/trans)-4-<(tert-Butyldimethylsilyl)oxy>cyclohexanemethanol 
• 72-18-4 L-valine 
• 6306-52-1 L-valine methylester hydrochloride 
• 1456900-67-6 (S)-methyl 2-(2-chloro-N-(4-methoxybenzyl)acetamido)-3-methylbutanoate 

Downstream Products

• 1456900-77-8 (3R,6S)-5-ethoxy-6-isopropyl-1-(4-methoxybenzyl)-3-((4-oxocyclohexyl)methyl)-1,6-dihydropyrazin-2(3H)-one 
• 1456900-63-2 (S)-2-((R)-2-amino-3-(4-oxocyclohexyl)propanamido)-3-methylbutanoic acid 

Relevant academic research and scientific papers

The synthesis and biological testing of bacilysin analogues

A series of compounds based on the structure of bacilysin were synthesised and tested for antibacterial activity. The key steps in the syntheses are the coupling of an iodide to a diketopiperazine (DKP) and mono-lactim ether scaffold, respectively. The diastereoselectivity of the coupling reactions was dependant on the scaffold, with selectivity for DKP of about 4:1 and mono-lactim ether exceeding 98:2. Subsequent elaboration of the compounds to give open chain dipeptides and DKPs that mimic the structure of bacilysin but substitute the epoxy ketone for a saturated or unsaturated ketone is described. Overall yield from coupling to final product was between 5 and 21 %, with the yield of the saturated products notably higher. The open chain dipeptides demonstrated moderate antibacterial and antifungal activity.