ChemInform Abstract: A Facile Synthesis of Acylaminotetraoxyspirophosphoranes.

Zhang, N.‐J.; Lu, Haiyan; Chen, X.; Zhao, Yiwen

doi:10.1002/chin.199827225

Cited by 1 publication

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“…Ltd. (Shanghai, China). Compounds 1–8 were synthesized according to published methods . P‐ 15 N‐Gly was synthesized using H‐ 15 N‐Gly‐OH as starting material.…”

Section: Methodsmentioning

confidence: 99%

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Fragmentation of pentacoordinate spirobicyclic aminoacyl‐phosphoranes (P‐AAs) by electrospray ionization tandem mass spectrometry concerning P–O and P–N bond cleavage

Gao

Zhu

et al. 2011

Rapid Comm Mass Spectrometry

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The fragmentation pathways of both protonated and sodiated pentacoordinate spirobicyclic aminoacylphosphoranes (P-AAs) have been studied by electrospray ionization multi-stage mass spectrometry (ESI-MS(n)) in positive mode. The possible pathways and their mechanisms are elucidated through the combination of ESI-MS/MS, isotope ((15)N and (2)H) labeling and high-resolution Fourier transform ion cyclotron resonance (FTICR)-MS/MS. The relative Gibbs free energies (ΔG) of the product ions and possible fragmentation pathways are estimated at the B3LYP/6-31 G(d) level of theory. The theoretical calculations show that both protonated and sodiated P-AAs would quickly fragment before Berry pseudorotation. For protonated P-AAs, they have different tendencies to P-O or P-N bond cleavage. For sodiated P-AAs, the P-N bond is easier to cleave and produces the tetracoordinated phosphorus ion H. These results to some extent may give a clue to the chemistry of the active sites of phosphoryl transfer enzymes and will enrich the gas-phase ESI-MS ion chemistry of pentacoordinate phosphoranes.

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“…Ltd. (Shanghai, China). Compounds 1–8 were synthesized according to published methods . P‐ 15 N‐Gly was synthesized using H‐ 15 N‐Gly‐OH as starting material.…”

Section: Methodsmentioning

confidence: 99%

“…Compounds 1-8 were synthesized according to published methods. [27][28][29][30] P-15 N-Gly was synthesized using H-15 N-Gly-OH as starting material. For the deuterium-labeled experiment, P-AAs (1 mg) were incubated with 1 mL CH 2 Cl 2 /CH 3 OD (1:5, v/v) for 3 h at room temperature for exchange of labile protons.…”

Section: Materials and Sample Preparationmentioning

confidence: 99%

Fragmentation of pentacoordinate spirobicyclic aminoacyl‐phosphoranes (P‐AAs) by electrospray ionization tandem mass spectrometry concerning P–O and P–N bond cleavage

Gao

Zhu

et al. 2011

Rapid Comm Mass Spectrometry

View full text Add to dashboard Cite

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ChemInform Abstract: A Facile Synthesis of Acylaminotetraoxyspirophosphoranes.

Cited by 1 publication

References 1 publication

Fragmentation of pentacoordinate spirobicyclic aminoacyl‐phosphoranes (P‐AAs) by electrospray ionization tandem mass spectrometry concerning P–O and P–N bond cleavage

Fragmentation of pentacoordinate spirobicyclic aminoacyl‐phosphoranes (P‐AAs) by electrospray ionization tandem mass spectrometry concerning P–O and P–N bond cleavage

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