Studies were carried out on the effect of decoupling, deuterium labeling, concentration, temperature, and solvent media on the NMR parameters of the vinyl phosphonate adduct of phenylalanine, C6H5CH2CH(COO-)NH2+CH2CH2PO(OCH2CH2C1)2. The results permit assignments of chemical shifts and coupling constants to the various protons of this molecule which contains unique structural features. The NH2+-CH2-protons are deshielded by more than 1 ppm than the CH2-PO-protons. The -OCH2-protons are nonequivalent exhibiting a fine split. Possible sources of the fine split include NH...O=P hydrogen bonding. The deuterium-labeling method should be applicable for synthesizing deuterium-and tritium-labeled crosslinked amino acids such as lysinoalanine and lanthionine and demonstrating analgous dehydroalanine-alpha-amino group-crosslinking.
CITATION STYLE
Friedman, M., & Boyd, W. A. (1977). A nuclear magnetic double resonance study of N-beta-bis-(beta’-chloroethyl) phosphonylethyl-DL-phenylalanine. Advances in Experimental Medicine and Biology, 86 A, 727–743. https://doi.org/10.1007/978-1-4684-3282-4_43
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