PMID- 27727023
OWN - NLM
STAT- MEDLINE
DCOM- 20170322
LR  - 20170322
IS  - 1873-376X (Electronic)
IS  - 1570-0232 (Linking)
VI  - 1047
DP  - 2017 Mar 15
TI  - Meaning and consequence of the coexistence of competitive hydrogen bond/salt 
      forms on the dissociation orientation of non-covalent complexes.
PG  - 45-58
LID - S1570-0232(16)30948-5 [pii]
LID - 10.1016/j.jchromb.2016.09.038 [doi]
AB  - Non-covalent complexes (NCC) between hexose monophosphates (HexP) and arginine 
      (R) were analyzed using ESI MS and MS/MS in negative mode under different (hard, 
      HC and soft, SC) desolvation conditions. High resolution mass spectrometry (HRMS) 
      revealed the presence of different ionic species, namely, homo- and 
      heteromultimers of R and HexP. Deprotonated heterodimers and corresponding 
      sodiated species were enhanced under HC likely due to a decrease in available 
      charge number associated with the reduction of H(+)/Na(+) exchange. The quantum 
      calculations showed that the formation of covalent systems is very little 
      exothermic, therefore, such systems are disfavored. Desolvation dependent CID 
      spectra of deprotonated [(HexP+R)‒H](-) complexes demonstrated that they can 
      exist within the hydrogen bond (HB) and salt bridge (SB) forms, yielding either 
      NCC separation or covalent bond cleavages, respectively. Although HB forms are 
      the main species, they cannot survive under HC; therefore, the minor SB forms 
      became detectable. Energy-resolved mass spectrometry (ERMS) experiments revealed 
      diagnostic fragment ions from both SB and HB forms, providing evidence that these 
      isomeric forms are inconvertible. SB formation should result from the ionic 
      interactions of highly acidic group of HexP with strongly basic guanidine group 
      of arginine and thus requires an arginine zwitterion (ZW) form. This was 
      confirmed by quantum calculations. Ion-ion interactions are significantly 
      affected by the presence of sodium cation as demonstrated by the fragmentation 
      patterns of sodiated complex species. Regarding CID data, only SB between 
      protonated amino group of R and deprotonated phosphate group of HexP could be 
      suggested, but the primary amine is not enough basic then, the SB must be 
      fleeting. Nevertheless, the observation of the covalent bond cleavages suggests 
      the presence of structures with a free negative charge able to induce 
      fragmentations. Indeed, according to quantum calculations, solvated salt (SS) 
      systems involving Na(+)/COO(-) salt solvated by neutral phosphate and negative 
      charge on sugar ring are preferentially formed.
CI  - Copyright (c) 2016 Elsevier B.V. All rights reserved.
FAU - Darii, Ekaterina
AU  - Darii E
AD  - CEA, Institut de Genomique, Genoscope, CNRS-UMR8030, Universite d'Evry Val 
      d'Essonne Evry, France. Electronic address: edariy@genoscope.cns.fr.
FAU - Alves, Sandra
AU  - Alves S
AD  - Universite Paris VI (UPMC), CNRS‒UMR 8232, IPMC, 4 Place Jussieu, 75255, Paris 
      Cedex 05, France.
FAU - Gimbert, Yves
AU  - Gimbert Y
AD  - Universite Grenoble Alpes (DCM), CNRS-UJF 5250, BP 38041, Grenoble Cedex 9, 
      France.
FAU - Perret, Alain
AU  - Perret A
AD  - CEA, Institut de Genomique, Genoscope, CNRS-UMR8030, Universite d'Evry Val 
      d'Essonne Evry, France.
FAU - Tabet, Jean-Claude
AU  - Tabet JC
AD  - Universite Paris VI (UPMC), CNRS‒UMR 8232, IPMC, 4 Place Jussieu, 75255, Paris 
      Cedex 05, France; CEA, iBiTec-S, SPI, LEMM, Gif Sur Yvette, France.
LA  - eng
PT  - Journal Article
DEP - 20160926
PL  - Netherlands
TA  - J Chromatogr B Analyt Technol Biomed Life Sci
JT  - Journal of chromatography. B, Analytical technologies in the biomedical and life 
      sciences
JID - 101139554
RN  - 0 (Fructosephosphates)
RN  - 0 (Glucosephosphates)
RN  - 15978-08-2 (fructose-1-phosphate)
RN  - 56-73-5 (Glucose-6-Phosphate)
RN  - 6814-87-5 (fructose-6-phosphate)
RN  - 94ZLA3W45F (Arginine)
RN  - CIX3U01VAU (glucose-1-phosphate)
SB  - IM
MH  - Arginine/*chemistry
MH  - Fructosephosphates/*chemistry
MH  - Glucose-6-Phosphate/*chemistry
MH  - Glucosephosphates/*chemistry
MH  - Hydrogen Bonding
MH  - Isomerism
MH  - Models, Molecular
MH  - Spectrometry, Mass, Electrospray Ionization
MH  - Tandem Mass Spectrometry
MH  - Thermodynamics
EDAT- 2016/10/12 06:00
MHDA- 2017/03/23 06:00
CRDT- 2016/10/12 06:00
PHST- 2016/02/26 00:00 [received]
PHST- 2016/07/23 00:00 [revised]
PHST- 2016/09/25 00:00 [accepted]
PHST- 2016/10/12 06:00 [pubmed]
PHST- 2017/03/23 06:00 [medline]
PHST- 2016/10/12 06:00 [entrez]
AID - S1570-0232(16)30948-5 [pii]
AID - 10.1016/j.jchromb.2016.09.038 [doi]
PST - ppublish
SO  - J Chromatogr B Analyt Technol Biomed Life Sci. 2017 Mar 15;1047:45-58. doi: 
      10.1016/j.jchromb.2016.09.038. Epub 2016 Sep 26.