Electrospray tandem mass spectrometric studies of all twenty <i>N</i>‐phosphoryl amino acids

Cao, Shuting; Zhang, Jianchen; Xu, Jun; Liao, Xincheng; Zhao, Yufen

doi:10.1002/rcm.1176

Cited by 13 publications

(10 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The product ion c was formed from the intermediate ion b by the loss of an HP(O)(O i Pr) 2 molecule (166 Da). We have found that MS/MS fragmentation of the protonated molecules obtained from this series of phosphorylated compounds 2a – f was identical to that of the product ion scan of the protonated DIPP‐ala molecule reported earlier in our laboratory 15–17. It is worth noting that all of the phosphorylated compounds 2a – f produced the same product ion at m/z 106, which has been assigned as the protonated benzylideneamine d. The product ion scan of the sodiated adducts [M+Na] + afforded the product ions e and f by the consecutive loses of either one or two molecules of propylene.…”

Section: Resultssupporting

confidence: 80%

Study on [(4‐substituted benzoylamino)phenylmethyl]phosphonic acid diisopropyl esters under electrospray ionization tandem mass spectrometric conditions

Fang¹,

Fang²,

Zhu³

et al. 2007

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

Phosphonate esters were synthesized and investigated by positive ion electrospray ionization mass spectrometry (ESI-MS) in conjunction with tandem mass spectrometry (MS/MS). It was found that for the sodiated adduct there were two novel rearrangement reactions, in which the phosphoryl oxygen atom migrated to the carbonyl carbon and a cleavage occurred at the amide bond, or a benzylamine fragment was lost and the phosphorus was reduced. However, when the methyl group substituted for the isopropyl group, these migrations were inhibited. A possible mechanism was proposed, and high-resolution mass spectrometry was applied to identify the formula of these novel ions. These results showed that ESI-MS is a useful tool for the structural determination of phosphonate esters.

show abstract

Section: Resultssupporting

confidence: 80%

Study on [(4‐substituted benzoylamino)phenylmethyl]phosphonic acid diisopropyl esters under electrospray ionization tandem mass spectrometric conditions

Fang¹,

Fang²,

Zhu³

et al. 2007

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

show abstract

“…Distinctive fragmentation ions are produced in the MS of the 3c species (see Scheme ), because of the easier loss of an isopropyl group by β‐elimination from the precursor ion . All the product ions from 3c lose one or two 2‐methylprop‐1‐ene species (42 Da), giving ions at m/z 346, 246, and 204.…”

Section: Resultsmentioning

confidence: 99%

“…Distinctive fragmentation ions are produced in the MS of the 3c species (see Scheme 2), because of the easier loss of an isopropyl group by b-elimination from the precursor ion. [21][22][23][24] All the product ions from 3c lose one or two 2-methylprop-1ene species (42 Da), giving ions at m/z 346, 246, and 204. The b-position of the isopropoxyl group of the phosphonate has six hydrogen atoms, so this has a great probability to migrate one hydrogen to the bridging oxygen and give out one or two neutrals.…”

Section: Esi-ms Fragmentation Of 3a-fmentioning

confidence: 99%

A novel hydrogen migration of dialkylphosphonic acid esters using electrospray ionization tandem mass spectrometry

Zeng

Luo

Jiang

et al. 2011

Rapid Comm Mass Spectrometry

Self Cite

View full text Add to dashboard Cite

In this paper, attention is focused on analysis of the fragmentation of α-hydroxy-β-amino phosphonate esters designed as inhibitors of protein kinase A. An interesting proton migration mechanism in the cleavage of the P-C bond is investigated by electrospray ionization tandem mass spectrometry. A possible rearrangement mechanism is proposed and verified by high-resolution mass spectra using isotope deuterium/hydrogen-exchange technology and additionally checked by detailed DFT calculation based on Gaussian software. The result clearly indicates that this mechanism proceeds by a five-membered ring concerted transition state with activation energy 11.3 kcal mol(-1) for the compound 3f. The overall reaction is endothermic with an energy 13.2 kcal mol(-1). The effect of different substituents and different metal ions for rearrangement of these esters is studied by experiment and theory. It is concluded that this rearrangement process is energetically unfavorable and hence only occurs in the mass spectrometer.

show abstract

“…Phosphonic and sulfonic acids can be interesting amino acid analogues that have stronger acidity than common carboxyl amino acids. Phosphorylated amino acids may also be used as building blocks for synthesizing phosphorylated peptides [51]. Synthetic ligands and receptors have been developed that feature these groups and their selectivity for guanidinium groups has been demonstrated as well [43][44][45]48].…”

Section: Aim Of the Studymentioning

confidence: 99%

Development of a screening technique for noncovalent complex formation between guanidinium- and phosphonate-functionalized amino acids by electrospray ionization ion trap mass spectrometry: assessing ionization and functional group interaction

Schug

Lindner

2004

International Journal of Mass Spectrometry

View full text Add to dashboard Cite

Electrospray tandem mass spectrometric studies of all twenty N‐phosphoryl amino acids

Cited by 13 publications

References 16 publications

Study on [(4‐substituted benzoylamino)phenylmethyl]phosphonic acid diisopropyl esters under electrospray ionization tandem mass spectrometric conditions

Study on [(4‐substituted benzoylamino)phenylmethyl]phosphonic acid diisopropyl esters under electrospray ionization tandem mass spectrometric conditions

A novel hydrogen migration of dialkylphosphonic acid esters using electrospray ionization tandem mass spectrometry

Development of a screening technique for noncovalent complex formation between guanidinium- and phosphonate-functionalized amino acids by electrospray ionization ion trap mass spectrometry: assessing ionization and functional group interaction

Contact Info

Product

Resources

About