The Malaysian Journal of Analytical Sciences Vol 17 No 1 (2013): 193 – 199

 

 

 

LIPIDIZATION OF SIMPLE AND DI-FUNCTIONAL AMINO ACIDS  

 

(Penglipidan Asid Amino Ringkas dan Dwi-Fungsi)

 

Zainab Idris, Mohd. Wahid Samsudin^* and Salmiah Ahmad

 

School of Chemical Sciences and Food Technology, Faculty of Science and Technology

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia

 

*Corresponding author: wahid@ukm.my

 

 

Abstract

This paper discuss the modification of azelaic acid into its applicable form by attachment of both its carboxyl sites to N-terminal of amino acid ethyl ester forming  amide linkages in anhydrous medium. Acylation of glycine ethyl ester hydrochloride with azelaic acid dichloride was best conducted in a 100% anhydrous medium. L-amino acid ethyl ester bearing a primary hydroxyl group on its side chain gave mixtures of product and variation in composition depending on the mole ratio of reactants used. Reduction in purity was also observed for L-amino acid ethyl ester with primary –SH group on its side chain as compared to L-amino acid ethyl ester having –SCH₃ group on the L-amino acid side chain. The diamidoester of azelaic acid with L-alanine ethyl ester, L-valine ethyl ester, L-leucine ethyl ester and L-glutamic acid diethyl ester were in good yield when prepared through the modified Schotten-Baumann reaction conditions.

 

Keywords: Azelaic acid dichloride, L-amino acid ethyl ester, Schotten-Bauman condition, Glycine ethyl ester hydrochloride 

 

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