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 -