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A semiempirical SCF MO study of the interaction of odorant molecules with a biological substrate
Author(s) -
Wu C. S.,
Myers L. J.,
Worley S. D.
Publication year - 1992
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.560440413
Subject(s) - chemistry , enthalpy , lysine , nucleophile , molecule , substrate (aquarium) , benzaldehyde , computational chemistry , amino acid , stereochemistry , organic chemistry , thermodynamics , biochemistry , ecology , physics , catalysis , biology
The AM 1 semiempirical SCF MO method developed by Dewar and co‐workers has been employed to compute possible interaction processes of the odorant molecules cocaine, methyl benzoate, and benzaldehyde with the biological substrate lysine. The only process predicted as possible in each case was nucleophilic attack on the carbonyl carbons of each odorant by the nitrogen lone pairs on lysine. The remote amino group of lysine in each case was predicted to react with lower activation enthalpy than did the α‐amino group, a prediction consistent with preliminary experimental data from these laboratories. Although the computed activation enthalpies were high (ca. 40 kcal mol −1 ) for the gas‐phase processes, it is conceivable that such processes could occur by alternate pathways with considerably lower ctivation energies in solvated media such as exists in the presence of mucus‐containing olfactory binding protein in vertebrate olfactory reception. © 1992 John Wiley & Sons, Inc.