Properties of Gaseous Deprotonated L-Cysteine S-Sulfate Anion [cysS-SO(3)](-): Intramolecular H-Bond Network, Electron Affinity, Chemically Active Site, and Vibrational Fingerprints.
Properties of Gaseous Deprotonated L-Cysteine S-Sulfate Anion [cysS-SO(3)](-): Intramolecular H-Bond Network, Electron Affinity, Chemically Active Site, and Vibrational Fingerprints.
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气态去质子化 L-半胱氨酸 S-硫酸根阴离子 [cysS-SO3] 的性质 —：分子内氢键网络、电子亲和力、化学活性位点和振动指纹
DOI：
10.3390/ijms24021682
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发表时间：
2023-01-14
影响因子：
5.6
通讯作者：
Cui, Zhifeng
中科院分区：
文献类型：
--
作者：
Wang, Qiaolin;Qin, Zhengbo;Hou, Gao-Lei;Yang, Zheng;Valiev, Marat;Wang, Xue-Bin;Zheng, Xianfeng;Cui, Zhifeng
L-cysteine S-sulfate, Cys-SSO3H, and their derivatives play essential roles in biological chemistry and pharmaceutical synthesis, yet their intrinsic molecular properties have not been studied to date. In this contribution, the deprotonated anion [cysS-SO3]− was introduced in the gas phase by electrospray and characterized by size-selected, cryogenic, negative ion photoelectron spectroscopy. The electron affinity of the [cysS-SO3]• radical was determined to be 4.95 ± 0.10 eV. In combination with theoretical calculations, it was found that the most stable structure of [cysS-SO3]− (S1) is stabilized via three intramolecular hydrogen bonds (HBs); i.e., one O−H⋯⋯N between the –COOH and –NH2 groups, and two N−H⋯⋯O HBs between –NH2 and –SO3, in which the amino group serves as both HB acceptor and donor. In addition, a nearly iso-energetic conformer (S2) with the formation of an O−H⋯⋯N−H⋯⋯O−S chain-type binding motif competes with S1 in the source. The most reactive site of the molecule susceptible for electrophilic attacks is the linkage S atom. Theoretically predicted infrared spectra indicate that O−H and N−H stretching modes are the fingerprint region (2800 to 3600 cm−1) to distinguish different isomers. The obtained information lays out a foundation to better understand the transformation and structure–reactivity correlation of Cys-SSO3H in biologic settings.
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