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Inter- and intramolecular N-terminal methyl–side chain interactions in N-acetyl-L-glutamic acid oligomeric benzyl ester solutions. 1H NMR study

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Abstract.

Oligomeric N-acetyl-L-glutamic acid benzyl esters with exact residue number (2, 3 or 4) have been synthesized by a stepwise procedure. The aggregational behavior of these oligomeric molecules in dioxane and benzene has been investigated by use of 1H NMR. In particular, the concentration dependence of the 1H signals for the N-terminal CH3 protons has provided evidence that an intermolecular CH3···π interaction plays a critical role in the formation of aggregates and that an intramolecular CH3···π interaction occurs in the monomolecular state.

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Authors and Affiliations

  1. Department of Applied Chemistry, Nagoya Institute of Technology, Gokiso-cho, Showa-ku, Nagoya 466-8555, Japan, , , , ,

    Hirofumi Okabayashi, Makoto Ishida & Hideki Masuda

  2. Department of Biochemistry, School of Medicine, Kumamoto University, 2-2-1 Honjo, Kumamoto 860-0811, Japan, , , , ,

    Haruhiko Tamaoki

  3. Department of Chemistry, The University of Auckland, Private Bag 92019, Auckland, New Zealand, , , , ,

    Charmian J. O'Connor

Authors
  1. Hirofumi Okabayashi
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  2. Haruhiko Tamaoki
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  3. Makoto Ishida
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  4. Hideki Masuda
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  5. Charmian J. O'Connor
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Okabayashi, H., Tamaoki, H., Ishida, M. et al. Inter- and intramolecular N-terminal methyl–side chain interactions in N-acetyl-L-glutamic acid oligomeric benzyl ester solutions. 1H NMR study. Colloid Polym Sci 281, 190–195 (2003). https://doi.org/10.1007/s00396-002-0761-5

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  • DOI: https://doi.org/10.1007/s00396-002-0761-5

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