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. 2021 Jul 29;12(29):6983-6987.
doi: 10.1021/acs.jpclett.1c01743. Epub 2021 Jul 20.

Shape of Testosterone

Iker León  1 , Elena R Alonso  2   3 , Santiago Mata  1 , José L Alonso  1
Affiliations

Shape of Testosterone

Iker León et al. J Phys Chem Lett. .

Abstract

We have successfully characterized the structure of testosterone, one of the essential steroids, through high-resolution rotational spectroscopy. A single conformer has been detected, and a total of 404 transitions have been fitted, allowing a precise determination of the rotational constants. It allowed us to unravel that the isolated structure of testosterone adopts an extended disposition. The results obtained in this work highlight how using laser ablation techniques in combination with Fourier transform microwave techniques allow the study of large biomolecules or common pharmaceuticals. It is an important step toward studying relevant biomolecules and developing new analytical techniques with unprecedented sensitivity and resolution.

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Conflict of interest statement

The authors declare no competing financial interest.

Figures

Scheme 1
Scheme 1. Chemical Structure of Testosterone
The labels a–d are used to reference the different rings in refs (5) and (6).
Figure 1
Figure 1
(a) Broadband spectrum of testosterone in the 1.5–6.5 GHz frequency region using the LA-CP-FTMW spectrometer, highlighting the a-type R-branch progressions (J' ← J) originated by a single conformer of testosterone. (b) A comparison between a selected range of the experimental spectrum with the simulated one, with selected rotational transitions (J'´K'a,K'c ← JKa,Kc). As can be seen, there is an excellent agreement between theory and experiment.
Figure 2
Figure 2
A comparison between the two plausible configurations of testosterone. A top and side view of (a) structure 1 within the extended configuration and (b) structure 4 within the semifolded configuration. For each configuration, three conformers are possible differing in the hydroxyl group’s orientation, as indicated by the green arrow.
Figure 3
Figure 3
Relaxed PES rotating the C–C–O–H dihedral angle of the three lowest-energy conformers of testosterone within configuration I. The low barrier separating them explains why a single conformer is seen. A close-up view of the hydroxyl group position is shown, while a larger view of the structures can be found in the SI.
See this image and copyright information in PMC

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