caa a22 4500 465766552 CHVBK 20180323111915.0 cr unu---uuuuu 170327e19900501xx s 000 0 eng 10.1007/BF02544385 doi (NATIONALLICENCE)springer-10.1007/BF02544385 Preparation and physical properties of some C18 unsaturated fatty esters containing L -amino acid residues and methyl esters of N -stearoylamino acids [Elektronische Daten] [Marcel Lie Ken Jie, H. Lao, David Leung] A series of five C18 unsaturated fatty esters (1-5) containing anL-amino acid residue (glycine, alanine, valine, leucine, phenylalanine) was prepared from methyl 12-amino-9-cis-octadecenoate and five methylN-stearoyl-amino acid ester derivatives (6-10) from stearoyl chloride and the sameL-amino acids. The infrared analysis of compounds 1-5 showed characteristic absorption bands at 3300 and 1665 cm−1 for the amino and amido functions, while the amido function in compounds 6-10 gave absorption bands at 3300 and 1680 cm−1. The position of the amido group (peptide linkage) in compounds 1-5 was readily determined by mass spectral analysis.1H nuclear magnetic resonance (NMR) analysis showed a doublet at 7.15 ppm for the amide proton (NHCO) in compounds 1-5, while in compounds 6-10 the amide proton signal appeared at 6.0 ppm. In13C NMR, the amido carbonyl resonance appeared at 171-175 ppm. In compounds 1-5 the effect of the amide function on the ethylene carbon (C-9) gave a signal at 124.1-125.3 ppm, while the remaining ethylenic carbon appeared at 131.9-132.5 ppm. The methine carbon (C-12) of the alkenyl chain was shifted to 48.4-49.8 ppm, and the assignment of the various carbon nuclei in the amino acid residue was readily achieved. In the methylN-stearoylamino acid ester derivatives (6-10), the methine carbon adjacent to the amido system and alpha to the carbomethoxy group appeared between 41.2-57.0 ppm depending on the type of alkyl group present in the amino acid moiety. The phenyl system in compounds 5 and 10 was confirmed by the13C signals in the 127-136 ppm range and by the proton signals in the 7.0-7.27 ppm region. American Oil Chemists' Society, 1990 Lie Ken Jie Marcel Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut Lao H. Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut Leung David Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut Lipids Springer-Verlag 25/5(1990-05-01), 260-266 0024-4201 25:5<260 1990 25 11745 https://doi.org/10.1007/BF02544385 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02544385 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Lie Ken Jie Marcel Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut NATIONALLICENCE 700 1- Lao H. Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut NATIONALLICENCE 700 1- Leung David Department of Chemistry, University of Hong Kong, Pokfulam Road, Hong Kong aut NATIONALLICENCE 773 0- Lipids Springer-Verlag 25/5(1990-05-01), 260-266 0024-4201 25:5<260 1990 25 11745 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer