Enzymatic Synthesis of Fatty Hydroxamic Acids from Palm Oil

Abstract

Hydroxamic acids (N-hydroxy carboxylic amides) may be regarded as derivatives of both hydroxylamine and carboxylic acids. The general formula of hydroxamic acid is R-CO-NHOH. In recent years, hydroxamic acids derivatives have received a lot of attention due to their biological activity as growth factors, food additives, antibiotics, antifungal agents, cell division factor and metal chelators (1), enzyme inhibitors (2), matrix metalloproteinase (MMP) inhibitor (3-5) and tumor inhibitors (6). Their complexes with various metal ions have been used for analytical chemistry as reagents for gravimetric and spectrometric metal determination (7), as collector for rare earth mineral (8), and for metal ions extraction from aqueous media (9). Simple and polymeric hydroxamic acids have also been extensively investigated for several successful analytical separations of metal ions. Besides their ability to form complex with metal ions, long-chain hydroxamic acids, by modi-fication of the terminal OH group, are of considerable interest as efficient surfactants in the detergent industry (10).Hydroxamic acids, in general, have been synthesized by adopting Blatt's procedure (11). In this method, the reaction of an alkyl or aryl ester (RCOOEt) with hydroxylamine in the presence of alkali and the free acid is obtained by the addition of acid in the appropriate quantity in cold solution. However, this chemical method, which is in alkali system, could evoke decomposition or degradation of the desired products due to presence of double bond.An enzymatic route for the synthesis of hydroxamic acid, with the inherent advantages of selectivity, mild reaction conditions and enantioselection, is of considerable synthetic interest. The synthesis of alkanohyroxamic acids (N-acyl hydroxylamines) by Rhizomucor miehei lipase-catalyzed hydroxylaminolysis of fatty acids and soybean methyl ester was reported (12). Later, Candida parapsilopsis was also found to mediate 33 JOS

Enzymatic Synthesis of Phenyl Fatty Hydroxamic Acids from Canola and Palm Oils

“…This could be due at high amount of the enzyme many of the active site remain in the bulk of the enzyme and cannot be excess by the substrates. A similarly behavior was reported by Suhendra et al 20 for palm oil hydroxylaminolysis.…”

“…Initially, the reaction progressed rapidly, and then the reaction rate decreased due to the decrease of mass transfer into the active sites of the enzyme. A similar behavior was reported by Servat et al 16 for oleyl hydroxamic acid synthesis 16 and by Suhendra et al 20 for palm oil hydroxylaminolysis.…”

Enzymatic Synthesis of Fatty Hydrazides from Palm Oils

“…These results are in agreement with the biosynthesis of fatty hydroxamic acid reaction from palm oil 19) . Hexane was choose as the solvent in the continue reaction.…”

“…However, this rate is faster compared with the results of Suhendra et al 19) , which shows that the biosynthesis of fatty hydroxamic acid reaction from palm oil the maximum conversion at 30 h.…”

“…The calculation of conversion of hydrazinolysis was followed by Dedy et al 19) , which show the conversion of hydroxylaminolysis of palm oils. The percentages of conversion of hydrazinolysis of various products of palm oil are presented in and were calculated by using equation ( ).…”