Sensory Perception of Non-Deuterated and Deuterated Organic Compounds
Publikation: Beiträge in Zeitschriften › Zeitschriftenaufsätze › Forschung › begutachtet
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in: Chemistry - A European Journal, Jahrgang 27, Nr. 3, 13.01.2021, S. 1046-1056.
Publikation: Beiträge in Zeitschriften › Zeitschriftenaufsätze › Forschung › begutachtet
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TY - JOUR
T1 - Sensory Perception of Non-Deuterated and Deuterated Organic Compounds
AU - Salthammer, Tunga
AU - Monegel, Friederike
AU - Schulz, Nicole
AU - Uhde, Erik
AU - Grimme, Stefan
AU - Seibert, Jakob
AU - Hohm, Uwe
AU - Palm, Wolf Ulrich
N1 - © 2020 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
PY - 2021/1/13
Y1 - 2021/1/13
N2 - The chemical background of olfactory perception has been subject of intensive research, but no available model can fully explain the sense of smell. There are also inconsistent results on the role of the isotopology of molecules. In experiments with human subjects it was found that the isotope effect is weak with acetone and D6-acetone. In contrast, clear differences were observed in the perception of octanoic acid and D15-octanoic acid. Furthermore, a trained sniffer dog was initially able to distinguish between these isotopologues of octanoic acid. In chromatographic measurements, the respective deuterated molecule showed weaker interaction with a non-polar liquid phase. Quantum chemical calculations give evidence that deuterated octanoic acid binds more strongly to a model receptor than non-deuterated. In contrast, the binding of the non-deuterated molecule is stronger with acetone. The isotope effect is calculated in the framework of statistical mechanics. It results from a complicated interplay between various thermostatistical contributions to the non-covalent free binding energies and it turns out to be very molecule-specific. The vibrational terms including non-classical zero-point energies play about the same role as rotational/translational contributions and are larger than bond length effects for the differential isotope perception of odor for which general rules cannot be derived.
AB - The chemical background of olfactory perception has been subject of intensive research, but no available model can fully explain the sense of smell. There are also inconsistent results on the role of the isotopology of molecules. In experiments with human subjects it was found that the isotope effect is weak with acetone and D6-acetone. In contrast, clear differences were observed in the perception of octanoic acid and D15-octanoic acid. Furthermore, a trained sniffer dog was initially able to distinguish between these isotopologues of octanoic acid. In chromatographic measurements, the respective deuterated molecule showed weaker interaction with a non-polar liquid phase. Quantum chemical calculations give evidence that deuterated octanoic acid binds more strongly to a model receptor than non-deuterated. In contrast, the binding of the non-deuterated molecule is stronger with acetone. The isotope effect is calculated in the framework of statistical mechanics. It results from a complicated interplay between various thermostatistical contributions to the non-covalent free binding energies and it turns out to be very molecule-specific. The vibrational terms including non-classical zero-point energies play about the same role as rotational/translational contributions and are larger than bond length effects for the differential isotope perception of odor for which general rules cannot be derived.
KW - computational chemistry
KW - human subjects
KW - isotopologues
KW - odor perception
KW - trained sniffer dogs
KW - Chemistry
UR - http://www.scopus.com/inward/record.url?scp=85097229379&partnerID=8YFLogxK
U2 - 10.1002/chem.202003754
DO - 10.1002/chem.202003754
M3 - Journal articles
C2 - 33058253
AN - SCOPUS:85097229379
VL - 27
SP - 1046
EP - 1056
JO - Chemistry - A European Journal
JF - Chemistry - A European Journal
SN - 0947-6539
IS - 3
ER -