《Synthesis of Nα-protected amino acid/peptide Weinreb amides employing N,N’-carbonyldiimidazole as activating agent; studies on docking and antibacterial activities》 was written by Uma, K.; Lalithamba, H. S.; Raghavendra, M.; Chandramohan, Vivek; Anupama, C.. Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide And the article was included in ARKIVOC (Gainesville, FL, United States) in 2016. The article conveys some information:
An efficient method for the synthesis of Nα-protected amino/peptide Weinreb amides (N-methoxy-N-methylamides) employing N,N’-carbonyldiimidazole (CDI) has been achieved. Nα-protected amino/peptide acids were treated with N,N’-carbonyldiimidazole, followed by the addition of N,O-dimethylhydroxylamine hydrochloride salt to yield the desired compounds The synthesized compounds were mainly gums, a few were solids, after the simple workup, and were characterized by IR, 1H NMR, 13C NMR and HRMS. The Weinreb amides were subjected to in silico studies, to predict the preferred orientation and binding affinity between the mols. using scoring functions. The ligand N-Fmoc-L-Phe-N(OCH3)CH3 showed min. binding energy – 29.85 kcal/mol with Escherichia coli and the ligand N-Fmoc-L-Ala-N(OCH3)CH3 showed min. binding energy -24.79 kcal/mol with Pseudomonas aeruginosa, -25.01 kcal/mol with Staphylococcus aureus. Based on the min. binding energies, antibacterial activities have been conducted for a few of the synthesized compounds In the experiment, the researchers used many compounds, for example, (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide)
(S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide(cas: 87694-50-6) belongs to amides. Because of the greater electronegativity of oxygen, the carbonyl (C=O) is a stronger dipole than the N–C dipole. The presence of a C=O dipole and, to a lesser extent a N–C dipole, allows amides to act as H-bond acceptors.Application In Synthesis of (S)-N-Methyl-N-methoxy-2-(tert-butoxycarbonylamino)-4-methylpentanamide In primary and secondary amides, the presence of N–H dipoles allows amides to function as H-bond donors as well.
Referemce:
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics