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Preparation, characterization, and surface and biological properties of N ‐stearoyl amino acids
Author(s) -
Sivasamy A.,
Krishnaveni M.,
Rao P. G.
Publication year - 2001
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/s11746-001-0361-5
Subject(s) - micrococcus luteus , antimicrobial , differential scanning calorimetry , chemistry , amino acid , micrococcus , bacteria , escherichia coli , candida albicans , critical micelle concentration , nuclear chemistry , organic chemistry , biochemistry , microbiology and biotechnology , micelle , biology , aqueous solution , physics , genetics , gene , thermodynamics
Several lipoamino acids were synthesized, in which n ‐octadecanoic acid (stearic acid) was coupled with the α‐amino group of an amino acid. The products were characterized and their identities confirmed by advanced analytical techniques like Fourier transform infrared 1 H nuclear magnentic resonance spectroscopy, and differential scanning, calorimetry. Their surface properties, such as critical micelle concentration (CMC) and foaming properties, biodegradability, and antimicrobial activity were also evaluated. The N ‐stearoyl amino acids (NSA) had low CMC values, and some of them showed good foaming properties. They were screened for antimicrobial activity against the gram‐positive bacteria Staphylococcus aureus, Micrococcus luteus , and Bacillus cerceus , the gram‐negative bacteria Escherichia coli and Pseudomonas aeruginosa , and the yeast Candida albicans . All the compounds inhibited at least one of these organisms. N ‐Stearoyl proline was the most effective, the order of antimicrobial activity being aromatic NSA> acidic NSA>basic NSA. However, the effective inhibition by all the compounds indicates the desirability of more thorough investigation and suggests that some of these compounds may have potential utility as biostatic additives in commercial products. All NSA are highly biodegradable and can readily be removed under conditions of normal secondary sewage treatment.