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Title: UV-Photochemistry of the Disulfide Bond: Evolution of Early Photoproducts from Picosecond X-ray Absorption Spectroscopy at the Sulfur K-Edge

Abstract

We have investigated dimethyl disulfide as the basic moiety for understanding the photochemistry of disulfide bonds, which are central to a broad range of biochemical processes. Picosecond time-resolved X-ray absorption spectroscopy at the sulfur K-edge provides unique element-specific insight into the photochemistry of the disulfide bond initiated by 267 nm femtosecond pulses. We observe a broad but distinct transient induced absorption spectrum which recovers on at least two time scales in the nanosecond range. We then employed RASSCF electronic structure calculations to simulate the sulfur-1s transitions of multiple possible chemical species, and identified the methylthiyl and methylperthiyl radicals as the primary reaction products. In addition, we identify disulfur and the CH2S thione as the secondary reaction products of the perthiyl radical that are most likely to explain the observed spectral and kinetic signatures of our experiment. Our study underscores the importance of elemental specificity and the potential of time-resolved X-ray spectroscopy to identify short-lived reaction products in complex reaction schemes that underlie the rich photochemistry of disulfide systems.

Authors:
 [1];  [2];  [1];  [3];  [4];  [5];  [6];  [1]; ORCiD logo [6];  [7]; ORCiD logo [8]; ORCiD logo [1]
  1. Univ. of Hamburg and Max Planck Inst. for the Structure and Dynamics of Matter (MPSD), Hamburg (Germany). Center for Free Electron Laser Science (CFEL) and Dept. of Physics
  2. Univ. of Hamburg and Max Planck Inst. for the Structure and Dynamics of Matter (MPSD), Hamburg (Germany). Center for Free Electron Laser Science (CFEL) and Dept. of Physics; Pakistan Inst. of Engineering and Applied Sciences, Nilore (Pakistan). Dept. of Physics and Applied Mathematics
  3. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Ultrafast X-ray Science Lab. and Chemical Sciences Division; SLAC National Accelerator Lab., Menlo Park, CA (United States). Photon Ultrafast Laser Science and Engineering Inst. (PULSE)
  4. Pusan National Univ., Busan (Korea, Republic of). Dept. of Chemistry and Chemistry Inst. of Functional Materials; Korea Research Inst. of Standards and Science, Daejeon (Korea, Republic of). Center for Gas Analysis and Division of Metrology for Quality of Life
  5. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Ultrafast X-ray Science Lab. and Chemical Sciences Division; Pohang Accelerator Lab. (PAL) (Korea, Republic of)
  6. Pusan National Univ., Busan (Korea, Republic of). Dept. of Chemistry and Chemistry Inst. of Functional Materials
  7. Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States). Ultrafast X-ray Science Lab. and Chemical Sciences Division; SLAC National Accelerator Lab., Menlo Park, CA (United States). Linac Coherent Light Source (LCLS)
  8. Deutsches Elektronen-Synchrotron (DESY) and Hamburg Centre for Ultrafast Imaging (CUI), Hamburg (Germany). Center for Free-Electron Laser Science (CFEL); Aarhus Univ. (Denmark). Dept. of Physics and Astronomy
Publication Date:
Research Org.:
Lawrence Berkeley National Lab. (LBNL), Berkeley, CA (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES). Chemical Sciences, Geosciences, and Biosciences Division; USDOE Office of Science (SC), Basic Energy Sciences (BES). Scientific User Facilities Division; National Research Foundation of Korea (NRF); Max Planck Society, Munich (Germany); German Research Foundation (DFG)
OSTI Identifier:
1461352
Grant/Contract Number:  
AC02-05CH11231; 2016R1E1A1A01941978; 2014R1A4A1001690; 2016K1A4A4A01922028
Resource Type:
Accepted Manuscript
Journal Name:
Journal of the American Chemical Society
Additional Journal Information:
Journal Volume: 140; Journal Issue: 21; Related Information: 10.1021/jacs.7b13455; Journal ID: ISSN 0002-7863
Publisher:
American Chemical Society (ACS)
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; disulfide; sulfur; X-ray spectroscopy

Citation Formats

Ochmann, Miguel, Hussain, Abid, von Ahnen, Inga, Cordones, Amy A., Hong, Kiryong, Lee, Jae Hyuk, Ma, Rory, Adamczyk, Katrin, Kim, Tae Kyu, Schoenlein, Robert W., Vendrell, Oriol, and Huse, Nils. UV-Photochemistry of the Disulfide Bond: Evolution of Early Photoproducts from Picosecond X-ray Absorption Spectroscopy at the Sulfur K-Edge. United States: N. p., 2018. Web. https://doi.org/10.1021/jacs.7b13455.
Ochmann, Miguel, Hussain, Abid, von Ahnen, Inga, Cordones, Amy A., Hong, Kiryong, Lee, Jae Hyuk, Ma, Rory, Adamczyk, Katrin, Kim, Tae Kyu, Schoenlein, Robert W., Vendrell, Oriol, & Huse, Nils. UV-Photochemistry of the Disulfide Bond: Evolution of Early Photoproducts from Picosecond X-ray Absorption Spectroscopy at the Sulfur K-Edge. United States. https://doi.org/10.1021/jacs.7b13455
Ochmann, Miguel, Hussain, Abid, von Ahnen, Inga, Cordones, Amy A., Hong, Kiryong, Lee, Jae Hyuk, Ma, Rory, Adamczyk, Katrin, Kim, Tae Kyu, Schoenlein, Robert W., Vendrell, Oriol, and Huse, Nils. Thu . "UV-Photochemistry of the Disulfide Bond: Evolution of Early Photoproducts from Picosecond X-ray Absorption Spectroscopy at the Sulfur K-Edge". United States. https://doi.org/10.1021/jacs.7b13455. https://www.osti.gov/servlets/purl/1461352.
@article{osti_1461352,
title = {UV-Photochemistry of the Disulfide Bond: Evolution of Early Photoproducts from Picosecond X-ray Absorption Spectroscopy at the Sulfur K-Edge},
author = {Ochmann, Miguel and Hussain, Abid and von Ahnen, Inga and Cordones, Amy A. and Hong, Kiryong and Lee, Jae Hyuk and Ma, Rory and Adamczyk, Katrin and Kim, Tae Kyu and Schoenlein, Robert W. and Vendrell, Oriol and Huse, Nils},
abstractNote = {We have investigated dimethyl disulfide as the basic moiety for understanding the photochemistry of disulfide bonds, which are central to a broad range of biochemical processes. Picosecond time-resolved X-ray absorption spectroscopy at the sulfur K-edge provides unique element-specific insight into the photochemistry of the disulfide bond initiated by 267 nm femtosecond pulses. We observe a broad but distinct transient induced absorption spectrum which recovers on at least two time scales in the nanosecond range. We then employed RASSCF electronic structure calculations to simulate the sulfur-1s transitions of multiple possible chemical species, and identified the methylthiyl and methylperthiyl radicals as the primary reaction products. In addition, we identify disulfur and the CH2S thione as the secondary reaction products of the perthiyl radical that are most likely to explain the observed spectral and kinetic signatures of our experiment. Our study underscores the importance of elemental specificity and the potential of time-resolved X-ray spectroscopy to identify short-lived reaction products in complex reaction schemes that underlie the rich photochemistry of disulfide systems.},
doi = {10.1021/jacs.7b13455},
journal = {Journal of the American Chemical Society},
number = 21,
volume = 140,
place = {United States},
year = {2018},
month = {5}
}

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Figures / Tables:

Figure 1 Figure 1: A.  Sulfur  K‐edge  spectrum  of  DMDS  along  with  the computed lowest sulfur‐1s transitions. B. Differential absorption spectra at  time delays of 0.1, 5, 50, and 150 ns after excitation with  267 nm  pulses.  C.  Time  evolution  of  the  absorbance changes  at  three  distinct  photon  energies,  indicated  by  color‐ coded  arrows  in  panel  B  (spheres  and  doted  lines)  along  with exponential decays (solid lines) fit to the experimental data. 

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