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1 H‐ and 13 C‐NMR studies of N ‐acetyl‐ L ‐alanine methylester and N ‐acetyl‐ L ‐alanine methylamide. I. Self‐association
Author(s) -
Asakura Tetsuo,
Kamio Masaru,
Nishioka Atsuo
Publication year - 1979
Publication title -
biopolymers
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.556
H-Index - 125
eISSN - 1097-0282
pISSN - 0006-3525
DOI - 10.1002/bip.1979.360180219
Subject(s) - chemistry , dimer , molecule , alanine , hydrogen bond , intermolecular force , stereochemistry , crystallography , amino acid , organic chemistry , biochemistry
The 1 H‐ and 13 C‐NMR spectra of N ‐acetyl‐ L ‐alanine methylester and N ‐acetyl‐ L ‐alanine methylamide were measured to examine the modes of self‐association of these molecules in solution. The different dilution shifts between these molecules seem to correspond to the difference in the associated state for each molecule. Consequently, for the former molecule, a dimer model forming the intermolecular hydrogen bond through Ala NH hydrogen atom in one molecule to Ala CO oxygen atom in another molecule was proposed. Another dimer model, which coincides with that proposed recently by Neel and coworkers, was proposed for the latter molecule. This second dimer model forms an intermolecular hydrogen bond through the NH of the N ‐methylamide group in one molecule to the acetyl CO in another molecule.