Wahyudi, Hendra; Tantisantisom, Worawan; Liu, Xuechao; Ramsey, Deborah M.; Singh, Erinprit K.; McAlpine, Shelli R. published the artcile< Synthesis, structure-activity analysis, and biological evaluation of sanguinamide B analogues>, Quality Control of 96929-05-4, the main research area is sanguinamide B analog synthesis antibacterial structure activity twitching motility; natural product antibiotic sanguinamide conformation conformer; peptide coupling Hantzsch cyclocondensation macrocyclization.
We report the first synthesis of sanguinamide B analogs. Substituting N-methylated (N-Me) amino acids, glycine (Gly), and L- or D-phenylalanine (Phe) into the backbone of sanguinamide B showed that only L- and D-Phe residues controlled the macrocycle conformation. The N-methylated and glycine analogs all had multiple conformations, whereas the L- and D-Phe derivatives only had a single conformation. Testing of all conformer analogs showed that inclusion of an L- or D-Phe was a superior design element than incorporating the N-Me moiety that is often utilized to control macrocyclic conformation. Finally, we show that there is an ideal Phe residue (in this case L-Phe) for generating compounds that have the greatest inhibitory effect on bacterial motility. Our data support the hypothesis that the macrocyclic conformation is dictated by the benzyl moiety requiring a ‘pseudoequatorial’ position, and all other energy considerations are secondary.
Journal of Organic Chemistry published new progress about Antibacterial agents. 96929-05-4 belongs to class thiazole, and the molecular formula is C12H18N2O4S, Quality Control of 96929-05-4.
Referemce:
Thiazole | C3H3NS – PubChem,
Thiazole | chemical compound | Britannica