Combining Near-UV Photodissociation with Electron Transfer. Reduction of the Diazirine Ring in a Photomethionine-Labeled Peptide Ion
详细信息 查看全文
- 作者：Christopher J. Shaffer ; Ale? Marek…
- 关键词：Electron transfer dissociation ; UV ; photodissociation ; Photomethionine ; Ion structures ; Dissociation kinetics
- 刊名：Journal of The American Society for Mass Spectrometry
- 出版年：2015
- 出版时间：August 2015
- 年：2015
- 卷：26
- 期：8
- 页码：1367-1381
- 全文大小：2,700 KB
- 参考文献：1.Suchanek, M., Radzikowska, A., Thiele, C.: Photo-leucine and photo-methionine allow identification of protein–protein interactions in living cells. Nat. Methods 2, 261-68 (2005)View Article
2.Hashimoto, M., Hatanaka, Y.: Recent progress in diazirine-based photoaffinity labeling. Eur. J. Org. Chem. 15, 2513-523 (2008)View Article
3.Das, J.: Aliphatic diazirines as photoaffinity probes for proteins: recent developments. Chem. Rev. 111, 4405-417 (2011)View Article
4.Liu, M.T.H.: Chemistry of diazirines Vol. I and II. CRC Press, Boca Raton (1987)
5.Shaffer, C.J., Marek, A., Pepin, R., Slováková, K., Ture?ek, F.: Combining UV photodissociation with electron transfer for peptide structure analysis. J. Mass Spectrom. 50, 470-75 (2015)View Article
6.Marek, A., Turecek, F.: Collision-induced dissociation of diazirine-labeled peptide ions. evidence for Br?nsted-acid assisted elimination of nitrogen. J. Am. Soc. Mass Spectrom. 25, 778-89 (2014)View Article
7.Marek, A., Pepin, R., Peng, B., Laszlo, K.J., Bush, M.F., Ture?ek, F.: Electron transfer dissociation of photolabeled peptides. backbone cleavages compete with diazirine ring rearrangements. J. Am. Soc. Mass Spectrom. 24, 1641-653 (2013)View Article
8.Marek, A., Shaffer, C.J., Pepin, R., Slováková, K., Laszlo, K.J., Bush, M.F., Ture?ek, F.: Electron transfer reduction of the diazirine ring in peptide gas-phase ions. on the peculiar loss of [NH4O] from photoleucine. J. Am. Soc. Mass Spectrom. 26, 415-31 (2015)View Article
9.Janz, J.M., Ren, Y., Looby, R., Kazmi, M.A., Sachdev, P., Grunbeck, A., Haggis, L., Chinnapen, D., Lin, A.Y., Seibert, C., McMurry, T., Carlson, K.E., Muir, T.W., Hunt, S., Sakmar, T.P.: Direct interaction between an allosteric agonist pepducin and the chemokine receptor CXCR4. J. Am. Chem. Soc. 133, 15878-5881 (2011)View Article
10.Coste, J., LeNguyen, D., Castro, B.: PyBOP: a new peptide coupling reagent devoid of toxic by-product. Tetrahedron Lett. 31, 205-08 (1990)View Article
11.Frisch, M.J., Trucks, G.W., Schlegel, H.B., Scuseria, G.E., Robb, M.A., Cheeseman, J.R., Scalmani, G., Barone, V., Mennucci, B., Petersson, G.A., Nakatsuji, H., Caricato, M., Li, X., Hratchian, H.P., Izmaylov, A.F., Bloino, J., Zheng, G., Sonnenberg, J.L., Hada, M., Ehara, M., Toyota, K., Fukuda, R., Hasegawa, J., Ishida, M., Nakajima, T., Honda, Y., Kitao, O., Nakai, H., Vreven, T., Montgomery Jr., J.A., Peralta, J.E., Ogliaro, F., Bearpark, M., Heyd, J.J., Brothers, E., Kudin, K.N., Staroverov, V.N., Kobayashi, R., Normand, J., Raghavachari, K., Rendell, A., Burant, J.C., Iyengar, S.S., Tomasi, J., Cossi, M., Rega, N., Millam, J.M., Klene, M., Knox, J.E., Cross, J.B., Bakken, V., Adamo, C., Jaramillo, J., Gomperts, R., Stratmann, R.E., Yazyev, O., Austin, A.J., Cammi, R., Pomelli, C., Ochterski, J.W., Martin, R.L., Morokuma, K., Zakrzewski, V.G., Voth, G.A., Salvador, P., Dannenberg, J.J., Dapprich, S., Daniels, A.D., Farkas, O., Foresman, J.B., Ortiz, J.V., Cioslowski, J., Fox, D.J.: Gaussian 09, Revision A.02. Gaussian, Inc., Wallingford (2009)
12.Becke, A.D.: New mixing of Hartree-Fock and local density-functional theories. J. Chem. Phys. 98, 1372-377 (1993)View Article
13.Becke, A.D.: Density functional thermochemistry. III. The role of exact exchange. J. Chem. Phys. 98, 5648-652 (1993)View Article
14.Zhao, Y., Truhlar, D.G.: The M06 suite of density functionals for main group thermochemistry, thermochemical kinetics, noncovalent interactions, excited states, and transition elements: two new functionals and systematic testing of four M06-class functionals and 12 other functionals. Theor. Chem. Accounts 120, 215-41 (2008)View Article
15.Chai, J.D., Head-Gordon, M.: Systematic optimization of long-range corrected hybrid density functionals. J. Chem. Phys. 128, 084106/1-84106/15 (2008)View Article
16.Chai, J.D., Head-Gordon, M.: Long-range corrected hybrid density functionals with damped atom-atom dispersion corrections. Phys. Chem. Chem. Phys. 10, 6615-620 (2008)View Article
17.M?ller, C., Plesset, M.S.: A note on an approximation treatment for many-electron systems. Phys. Rev. 46, 618-22 (1934)View Article
18.Schlegel, H.B.: Potential energy curves using unrestricted Moller-Plesset perturbation theory with spin annihilation. J. Chem. Phys. 84, 4530 (1986)View Article
19.Mayer, I.: Spin-projected UHF method. IV. Comparison of potential curves given by different one-electron methods. Adv. Quantum Chem. 12, 189-62 (1980)
20.Ture?ek, F.: Proton affinity of dimethyl sulfoxide and relative stabilities of C2H6OS molecules and C2H7OS+ Ions. A comparative G2(MP2) ab initio and density functional theory study. J. Phys. Chem. A 102, 4703 (1998)View Article
21.Polá?ek, M., Ture?ek, F.: Hydrogen atom adducts to nitrobenzene. Formation of the phenylnitronic radical in the gas phase and energetics of Wheland intermediates. J. Am. Chem. Soc. 122, 9511-524 (2000)View Article
22.W - 作者单位：Christopher J. Shaffer (1)
Ale? Marek (1)
Huong T. H. Nguyen (1)
Franti?ek Ture?ek (1)
1. Department of Chemistry, University of Washington, Bagley Hall, Box 351700, Seattle, WA, 98195-1700, USA - 刊物主题：Analytical Chemistry; Biotechnology; Organic Chemistry; Proteomics; Bioinformatics;
- 出版者：Springer US
- ISSN：1879-1123
文摘
Electron transfer dissociation of peptide ions with the diazirine-containing residue photomethionine (M*) results in side-chain dissociations by loss of C3H7N2 radicals in addition to standard backbone cleavages. The side-chain dissociations are particularly prominent upon activation of long-lived, charge-reduced, cation radicals (GM*GGR + 2H)+?/sup>. Investigation of these cation radicals by near-UV photodissociation and collisional activation revealed different fragmentation products and mechanisms resulting from these ion activation modes. The dissociations observed for photomethionine were dramatically different from those previously reported for the lower homologue photoleucine; here, a difference by a single methylene group in the side chain had a large effect on the chemistries of the cation radicals upon ETD and further activation. ETD intermediates and products were probed by tandem 355-nm UV photodissociation-collision induced dissociation and found to contain chromophores that resulted from electron attachment to the diazirine ring. The nature of the newly formed chromophores and ion energetics and kinetics were investigated by electron structure calculations combining ab initio and density functional theory methods and Rice-Ramsperger-Kassel-Marcus (RRKM) theory. The dramatic difference between the dissociations of L* and M* containing peptide cation radicals is explained by electronic effects that play a role in stabilizing critical reaction intermediates and steer the dissociations into kinetically favored reaction channels. In addition, a new alternating UVPD-ETD-UVPD MS4 experiment is introduced and utilized for ion structure elucidation.