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N ‐acyl‐L‐leucines of biologically active uncommon fatty acids: Synthesis and antibacterial activity
Author(s) -
Mhaskar S. Y.,
Lakshminarayana G.,
Saisree L.
Publication year - 1993
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/bf02545362
Subject(s) - antibacterial activity , chemistry , biological activity , stereochemistry , fatty acid , biochemistry , bacteria , biology , genetics , in vitro
The effect of structural variation in the fatty acid chain on the antibacterial activity of N ‐acyl‐L‐leucines was investigated. Pure N ‐acyl leucines of some structurally different and biologically active uncommon fatty acids were synthesized for the first time and tested for antimicrobial activity. N ‐Stearoyl‐, N ‐oleoyl‐ and N ‐ricinoleoyl leucines were also evaluated for comparison. The N ‐acyl leucines exhibited greater activity in acid form than the methyl ester form and against gram positive bacteria than gram‐negative bacteria. The presence of a cyclopropane or a hydroxy group or unsaturation in the acyl chain increased the antibacterial activity. Shifting the hydroxyl group toward the amide linkage resulted in a diminished effect on the antibacterial activity.