Chalcogen bonds in selenocysteine seleninic acid, a functional GPx constituent, and in other seleninic or sulfinic acid derivatives

Tripathi, Abhishek, Daolio, Andrea, Pizzi, Andrea, Guo, Zhifang, Turner, David R., Baggioli, Alberto, Famulari, Antonino, Deacon, Glen B., Resnati, Giuseppe, and Singh, Harkesh B. (2021) Chalcogen bonds in selenocysteine seleninic acid, a functional GPx constituent, and in other seleninic or sulfinic acid derivatives. Chemistry: an Asian journal, 16 (16). pp. 2351-2360.

PDF (Published Version) - Published Version
Available under License Creative Commons Attribution.

Download (4MB) | Preview
View at Publisher Website:


The controlled oxidation reaction of L-selenocystine under neutral pH conditions affords selenocysteine seleninic acid (3-selenino-L-alanine) which is characterized also by means of single-crystal X-ray diffraction. This technique shows that selenium forms three chalcogen bonds (ChBs), one of them being outstandingly short. A survey of seleninic acid derivatives in the Cambridge Structural Database (CSD) confirms that the C−Se(=O)O− functionality tends to act as a ChB donor robust enough to systematically influence the interactional landscape in the solid. Quantum Theory of Atom in Molecules (QTAIM) analysis proves the attractive nature of the short contacts observed in crystals containing the seleninic functionality and calculation of surface molecular electrostatic potential (MEP) reveals that remarkably positive σ-holes can frequently be found opposite to the covalent bonds at selenium. Both CSD searches and QTAIM and MEP approaches show that also the sulfinic acid moiety can function as a ChB donor, albeit less frequently than the seleninic acid one. These findings may contribute to a better understanding, at the atomic level, of the mechanism of action of the enzymes that control oxidative stress and ROS deactivation and that contain selenocysteine seleninic acid and cysteine sulfinic acid in the active site.

Item ID: 75044
Item Type: Article (Research - C1)
ISSN: 1861-471X
Keywords: Amino Acids, Chalcogen Bond, Selenium, Selenocysteine, Sigma-hole
Copyright Information: © 2021 The Authors. Chemistry - An Asian Journal published by Wiley - VCH GmbH. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
Date Deposited: 11 Jul 2022 04:18
FoR Codes: 34 CHEMICAL SCIENCES > 3402 Inorganic chemistry > 340209 Organometallic chemistry @ 100%
SEO Codes: 28 EXPANDING KNOWLEDGE > 2801 Expanding knowledge > 280105 Expanding knowledge in the chemical sciences @ 50%
24 MANUFACTURING > 2499 Other manufacturing > 249999 Other manufacturing not elsewhere classified @ 50%
Downloads: Total: 613
Last 12 Months: 87
More Statistics

Actions (Repository Staff Only)

Item Control Page Item Control Page