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 shu

Investigation of _L/D-threonine substituted _L-serine octamer ions by mass spectrometry and infrared photodissociation spectroscopy

a.
The State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China
b.
Collaborative Innovation Center of Chemical Science and Engineering, Nankai University, Tianjin 300071, ;China

Corresponding author: Kong Xiang-Lei, kongxianglei@nankai.edu.cn
Received Date: 9 August 2016
Revised Date: 16 September 2016
Accepted Date: 30 September 2016
Available Online: 1 March 2016

Figures(3)

Threonine-substituted serine octamer ions were generated by electrospray ionization (ESI) and investigated by mass spectrometry and infrared photodissociation (IRPD) spectroscopy. IRPD spectra of[L-Ser₇+L/D-Thr₁]H⁺ and [L-Ser₆+L/D-Thr₂]H⁺ were obtained in the range of 2700-3600 cm^-1. Chiral differentiation was achieved by comparing their IRPD spectra. The main difference located in the range of 3300-3500 cm^-1. And the results indicate the substitution of L-Ser by D-Thr could weaken the intermolecular H-bonds and loosen the original structures of serine octamers.
- IRPD spectroscopy,
- Threonine,
- Serine octamer,
- Chiral differentiation,
- Mass spectrometry
1. [1]
  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
2. [2]
  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
3. [3]
  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
4. [4]
  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
5. [5]
  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
6. [6]
  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
7. [7]
  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
8. [8]
  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
9. [9]
  Gronert S., O'Hair R.A.J., Fagin A.E.. Ion/molecule reactions of the protonated serine octamer[J]. Chem. Commun., 2004:1944-1945.
10. [10]
  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
11. [11]
  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
12. [12]
  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.
13. [13]
  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
14. [14]
  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
15. [15]
  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
16. [16]
  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
17. [17]
  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
18. [18]
  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
19. [19]
  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
20. [20]
  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
21. [21]
  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
22. [22]
  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
1. [1]
  Yang Feng , Yang-Qing Tian , Yong-Qiang Zhao , Sheng-Jun Chen , Bi-Feng Yuan . Dynamic deformylation of 5-formylcytosine and decarboxylation of 5-carboxylcytosine during differentiation of mouse embryonic stem cells into mouse neurons. Chinese Chemical Letters, 2024, 35(11): 109656-. doi: 10.1016/j.cclet.2024.109656
2. [2]
  Tian Feng , Yun-Ling Gao , Di Hu , Ke-Yu Yuan , Shu-Yi Gu , Yao-Hua Gu , Si-Yu Yu , Jun Xiong , Yu-Qi Feng , Jie Wang , Bi-Feng Yuan . Chronic sleep deprivation induces alterations in DNA and RNA modifications by liquid chromatography-mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(8): 109259-. doi: 10.1016/j.cclet.2023.109259
3. [3]
  Cheng Guo , Xiaoxiao Zhang , Xiujuan Hong , Yiqiu Hu , Lingna Mao , Kezhi Jiang . Graphene as adsorbent for highly efficient extraction of modified nucleosides in urine prior to liquid chromatography-tandem mass spectrometry analysis. Chinese Chemical Letters, 2024, 35(4): 108867-. doi: 10.1016/j.cclet.2023.108867
4. [4]
  Junmeng Luo , Qiongqiong Wan , Suming Chen . Chemistry-driven mass spectrometry for structural lipidomics at the C=C bond isomer level. Chinese Chemical Letters, 2025, 36(1): 109836-. doi: 10.1016/j.cclet.2024.109836
5. [5]
  Keqiang Shi , Xiujuan Hong , Dongyan Xu , Tao Pan , Huiwen Wang , Hongru Feng , Cheng Guo , Yuanjiang Pan . Analysis of RNA modifications in peripheral white blood cells from breast cancer patients by mass spectrometry. Chinese Chemical Letters, 2025, 36(3): 110079-. doi: 10.1016/j.cclet.2024.110079
6. [6]
  Yongyi Li , Jin Han , Xiangyu Wang , Zhenwei Wei . In-situ reaction monitoring and kinetics study of photochemical reactions by optical focusing inductive electrospray mass spectrometry. Chinese Chemical Letters, 2025, 36(9): 110708-. doi: 10.1016/j.cclet.2024.110708
7. [7]
  Rui Su , Xiaowei Fang , Peng Zeng , Yong Qian , Xuanzhu Li , Huiyu Xing , Jiamei Lin , Jiaquan Xu . Mass spectrometry for non-destructive detection of the average diameter of micro copper wires. Chinese Chemical Letters, 2025, 36(10): 110748-. doi: 10.1016/j.cclet.2024.110748
8. [8]
  Qiongqiong Wan , Yanan Xiao , Guifang Feng , Xin Dong , Wenjing Nie , Ming Gao , Qingtao Meng , Suming Chen . Visible-light-activated aziridination reaction enables simultaneous resolving of C=C bond location and the sn-position isomers in lipids. Chinese Chemical Letters, 2024, 35(4): 108775-. doi: 10.1016/j.cclet.2023.108775
9. [9]
  Yao-Hua Gu , Yu Chen , Qing Li , Neng-Bin Xie , Xue Xing , Jun Xiong , Min Hu , Tian-Zhou Li , Ke-Yu Yuan , Yu Liu , Tang Tang , Fan He , Bi-Feng Yuan . Metabolome profiling by widely-targeted metabolomics and biomarker panel selection using machine-learning for patients in different stages of chronic kidney disease. Chinese Chemical Letters, 2024, 35(11): 109627-. doi: 10.1016/j.cclet.2024.109627
10. [10]
  Yimin Guo , Yiting Luo , Shuwen Hua , Chuan-Fan Ding , Yinghua Yan . Application of magnetic nanomaterials in peptidomics: A review in the past decade. Chinese Chemical Letters, 2025, 36(6): 110070-. doi: 10.1016/j.cclet.2024.110070
11. [11]
  Xiaoli Zhong , Liangsheng Chen , Hao Xu , Tianhang Jiang , Zhengyi Hua , Fancheng Tan , Xiaoya Mao , Ziquan Fan , Zhiwei Li , Jun Zeng , Shu-Hai Lin . Development of a comprehensive computational pipeline for cardiolipin atlas in an intermittent fasting model. Chinese Chemical Letters, 2025, 36(12): 111027-. doi: 10.1016/j.cclet.2025.111027
12. [12]
  Shu-Yi Gu , Tian Feng , Fang-Yin Gang , Si-Yu Yu , Wan Chan , Zhao-Cheng Ma , Yao-Hua Gu , Bi-Feng Yuan . Persistent organic pollutant perfluorooctanoic acid induces alterations in epigenetic modifications of DNA and RNA. Chinese Chemical Letters, 2025, 36(12): 110957-. doi: 10.1016/j.cclet.2025.110957
13. [13]
  Wei Shao , Wanqun Zhang , Pingping Zhu , Wanqun Hu , Qiang Zhou , Weiwei Li , Kaiping Yang , Xisheng Wang . Design and Practice of Ideological and Political Cases in the Course of Instrument Analysis Experiment: Taking the GC-MS Experiment as an Example. University Chemistry, 2024, 39(2): 147-154. doi: 10.3866/PKU.DXHX202309048
14. [14]
  Lu Huang , Jiang Wang , Hong Jiang , Lanfang Chen , Huanwen Chen . On-line determination of selenium compounds in tea infusion by extractive electrospray ionization mass spectrometry combined with a heating reaction device. Chinese Chemical Letters, 2025, 36(1): 109896-. doi: 10.1016/j.cclet.2024.109896
15. [15]
  Yanhua Chen , Xian Ding , Jun Zhou , Zhaoying Wang , Yunhai Bo , Ying Hu , Qingce Zang , Jing Xu , Ruiping Zhang , Jiuming He , Fen Yang , Zeper Abliz . Plasma metabolomics combined with mass spectrometry imaging reveals crosstalk between tumor and plasma in gastric cancer genesis and metastasis. Chinese Chemical Letters, 2025, 36(1): 110351-. doi: 10.1016/j.cclet.2024.110351
16. [16]
  Haiyan Lu , Jiayue Ye , Yiping Wei , Hua Zhang , Konstantin Chingin , Vladimir Frankevich , Huanwen Chen . Tracing molecular margins of lung cancer by internal extractive electrospray ionization mass spectrometry. Chinese Chemical Letters, 2025, 36(2): 110077-. doi: 10.1016/j.cclet.2024.110077
17. [17]
  Wen Su , Siying Liu , Qingfu Zhang , Zhongyan Zhou , Na Wang , Lei Yue . Temperature-controlled electrospray ionization tandem mass spectrometry study on protein/small molecule interaction. Chinese Chemical Letters, 2025, 36(5): 110237-. doi: 10.1016/j.cclet.2024.110237
18. [18]
  Peisi Xie , Jing Chen , Yongjun Xia , Zongwei Cai . MALDI and MALDI-2 mass spectrometry imaging contribute to revealing the alternations in lipid metabolism in germinating soybean seeds. Chinese Chemical Letters, 2025, 36(8): 110595-. doi: 10.1016/j.cclet.2024.110595
19. [19]
  Feng-Qing Huang , Yu Wang , Ji-Wen Wang , Dai Yang , Shi-Lei Wang , Yuan-Ming Fan , Raphael N. Alolga , Lian-Wen Qi . Chemical isotope labeling-assisted liquid chromatography-mass spectrometry enables sensitive and accurate determination of dipeptides and tripeptides in complex biological samples. Chinese Chemical Letters, 2024, 35(11): 109670-. doi: 10.1016/j.cclet.2024.109670
20. [20]
  Chao Zhao , Chenyu Gao , Zhiyi Yang , Tianyou Cao , Qian Luo , Zhijun Zhang . Whole brain lipid dyshomeostasis in depressive-like behavior young adult rats: Mapping by mass spectrometry imaging-based spatial omics. Chinese Chemical Letters, 2025, 36(10): 111089-. doi: 10.1016/j.cclet.2025.111089

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1352)
HTML views(125)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

Investigation of L/D-threonine substituted L-serine octamer ions by mass spectrometry and infrared photodissociation spectroscopy

Metrics

通讯作者: 陈斌, bchen63@163.com

Investigation of _L/D-threonine substituted _L-serine octamer ions by mass spectrometry and infrared photodissociation spectroscopy