Investigation of L/D-threonine substituted L-serine octamer ions by mass spectrometry and infrared photodissociation spectroscopy
- Corresponding author: Kong Xiang-Lei, kongxianglei@nankai.edu.cn
Citation:
Ren Juan, Wang Yi-Yun, Feng Ru-Xia, Kong Xiang-Lei. Investigation of L/D-threonine substituted L-serine octamer ions by mass spectrometry and infrared photodissociation spectroscopy[J]. Chinese Chemical Letters,
;2017, 28(3): 537-540.
doi:
10.1016/j.cclet.2016.10.032
Cooks R.G., Zhang D.X., Koch K.J., Gozzo F.C., Eberlin M.N.. Chiroselective selfdirected octamerization of serine:implications for homochirogenesis[J]. Anal. Chem., 2001,73:3646-3655. doi: 10.1021/ac010284l
Koch K.J., Gozzo F.C., Nanita S.C.. Chiral transmission between amino acids:chirally selective amino acid substitution in the serine octamer as a possible step in homochirogenesis[J]. Angew. Chem. Int. Ed., 2002,41:1721-1724. doi: 10.1002/(ISSN)1521-3773
Takats Z., Nanita S.C., Schlosser G., Vekey K., Cooks R.G.. Atmospheric pressure gasphase H/D exchange of serine octamers[J]. Anal. Chem., 2003,75:6147-6154. doi: 10.1021/ac034284s
Takats Z., Nanita S.C., Cooks R.G.. Serine octamer reactions:indicators of prebiotic relevance[J]. Angew. Chem. Int. Ed., 2003,42:3521-3523. doi: 10.1002/anie.200351210
Takats Z., Nanita S.C., Cooks R.G., Schlosser G., Vekey K.. Amino acid clusters formed by sonic spray ionization[J]. Anal. Chem., 2003,75:1514-1523. doi: 10.1021/ac0260793
Nanita S.C., Cooks R.G.. Serine octamers:cluster formation, reactions, and implications for biomolecule homochirality[J]. Angew. Chem. Int. Ed., 2006,45:554-559. doi: 10.1002/(ISSN)1521-3773
Counterman A.E., Clemmer D.E.. Magic number clusters of serine in the gas phase[J]. J. Phys. Chem. B, 2001,105:8092-8096. doi: 10.1021/jp011421l
Schalley C.A., Weis P.. Unusually stable magic number clusters of serine with a surprising preference for homochirality[J]. Int. J. Mass Spectrom., 2002,221:9-19. doi: 10.1016/S1387-3806(02)00955-7
Gronert S., O'Hair R.A.J., Fagin A.E.. Ion/molecule reactions of the protonated serine octamer[J]. Chem. Commun., 2004:1944-1945.
Hodyss R., Julian R.R., Beauchamp J.L.. Spontaneous chiral separation in noncovalent molecular clusters[J]. Chirality, 2001,13:703-706. doi: 10.1002/(ISSN)1520-636X
Julian R.R., Hodyss R., Kinnear B., Jarrold M.F., Beauchamp J.L.. Nanocrystalline aggregation of serine detected by electrospray ionization mass spectrometry:origin of the stable homochiral gas-phase serine octamer[J]. J. Phys. Chem. B, 2002,106:1219-1228. doi: 10.1021/jp012265l
Ustyuzhanin P., Ustyuzhanin J., Lifshitz C.. An electrospray ionization-flow tube study of H/D exchange in protonated serine[J]. Int. J. Mass Spectrom. 223-, 2003,224:491-498.
Mazurek U., Geller O., Lifshitz C.. Protonated serine octamer cluster:structure elucidation by gas-phase H/D exchange reactions[J]. J. Phys. Chem. A, 2005,109:2107-2112. doi: 10.1021/jp0451344
Oh H.B., Lin C., Hwang H.Y.. Infrared photodissociation spectroscopy of electrosprayed ions in a Fourier transform mass spectrometer[J]. J. Am. Chem. Soc., 2005,127:4076-4083. doi: 10.1021/ja040136n
Kong X.L., Tsai I.A., Sabu S.. Progressive stabilization of zwitterionic structures in[H (Ser)2-8]+ studied by infrared photodissociation spectroscopy[J]. Angew. Chem. Int. Ed., 2006,45:4130-4134. doi: 10.1002/(ISSN)1521-3773
Kong X.L., Lin C., Infusini G.. Numerous isomers of serine octamer ions characterized by infrared photodissociation spectroscopy[J]. ChemPhysChem, 2009,10:2603-2606. doi: 10.1002/cphc.v10:15
Sunahori F.X., Yang G.C., Kitova E.N., Klassen J.S., Xu Y.J.. Chirality recognition of the protonated serine dimer and octamer by infrared multiphoton dissociation spectroscopy[J]. Phys. Chem. Chem. Phys., 2013,15:1873-1886. doi: 10.1039/C2CP43296J
Liao G.H., Yang Y.J., Kong X.L.. Chirality effects on proline-substituted serine octamers revealed by infrared photodissociation spectroscopy[J]. Phys. Chem. Chem. Phys., 2014,16:1554-1558. doi: 10.1039/C3CP53469C
Yin H., Kong X.L.. Structure of protonated threonine dimers in the gas phase:saltbridged or charge-solvated[J]. J. Am. Soc. Mass Spectrom., 2015,26:1455-1461. doi: 10.1007/s13361-015-1194-y
Kong X.L.. Reinvestigation of the structure of protonated lysine dimer[J]. J. Am. Soc. Mass Spectrom., 2014,25:422-426. doi: 10.1007/s13361-013-0801-z
Feng R.X., Mu L., Yang S.M., Kong X.L.. Structure of Pro4H+ investigated by infrared photodissociation (IRPD) spectroscopy and theoretical calculations[J]. Chin. Chem. Lett., 2016,27:593-596. doi: 10.1016/j.cclet.2016.02.027
Cody R.B., Hein R.E., Goodman S.D., Marshall A.G.. Stored waveform inverse Fourier transform excitation for obtaining increased parent ion selectivity in collisionally activated dissociation:preliminary results[J]. Rapid Commun. Mass Spectrom., 1987,1:99-102. doi: 10.1002/(ISSN)1097-0231
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