720660-22-0

Upstream product

• 162554-06-5 methyl 4-(4-cyanobenzyl)benzoate 
• 126747-14-6 4-cyanophenylboronic acid 
• 2417-72-3 Methyl 4-(bromomethyl)benzoate 
• 99-75-2 4-methyl-benzoic acid methyl ester 

Downstream Products

• 183947-71-9 4-{4-[((S)-6-Benzyloxycarbonylamino-2-tert-butoxycarbonylamino-hexanoylamino)-methyl]-benzyl}-benzoic acid methyl ester 
• 162554-07-6 4-{4-[((S)-6-Amino-2-tert-butoxycarbonylamino-hexanoylamino)-methyl]-benzyl}-benzoic acid methyl ester 
• 183947-73-1 C₅₃H₆₈N₆O₁₀S 
• 162554-08-7 C₅₅H₇₂N₆O₁₀S 

Relevant academic research and scientific papers

A Novel Receptor for Amino Acid Derivatives

A novel macrobicycle featuring a thiourea as a carboxylate binding site, and amide functionality to provide further hydrogen-bonding interactions with suitable guests is prepared; the ability of this novel macrobicycle to bind simple amino acid derivative

Stabilization of a cis amide bond in a host-guest complex

Macrobicycle 12 has been synthesized and its binding properties with a range of N-acetyl amino acid carboxylates (as tetrabutylammonium salts) have been studied. While the binding results showed little selectivity for the various substrates investigated, detailed NMR studies have revealed that D-amino acid substrates bind predominantly on the outside of the macrobicycle cavity by a strong carboxylate-thiourea interaction, whereas L-amino acid substrates bind predominantly on the inside of the cavity also establishing a strong carboxylate-thiourea interaction but with the acetyl amide in a cis configuration. Molecular modeling studies suggest that the energetic penalty associated with adopting a cis amide configuration in the host-guest complex is compensated by intermolecular hydrogen bonds between the cis amide and the rim of the macrobicycle.