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A Nuclear Magnetic Double Resonance Study of N-β-Bis-(β′-Chloroethyl) Phosphonylethyl-DL-Phenylalanine

  • Mendel Friedman
  • Walter A. Boyd
Part of the Advances in Experimental Medicine and Biology book series (AEMB, volume 86A)

Abstract

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(OCH2CH2Cl)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+−CH 2 -protons are deshielded by more than 1 ppm than the CH 2 -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-α-amino group-crosslinking.

Keywords

Nuclear Magnetic Resonance Nuclear Magnetic Resonance Spectrum Vinyl Ketone Nuclear Magnetic Resonance Parameter Sulfonium Salt 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Plenum Press, New York 1977

Authors and Affiliations

  • Mendel Friedman
    • 1
  • Walter A. Boyd
    • 1
  1. 1.Agricultural Research Service, U. S. Department of AgricultureNorthern Regional Research LaboratoryPeoriaUSA

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