Characterization of Betidamino Acid-Containing Somatostatin and Gonadotropin-Releasing Hormone Analogs with Electrospray Mass Spectrometry and Tandem Mass Spectrometry

Craig, A. Grey; DeBoard, Ryan; Kirby, Dean A.; Jiang, Guangcheng; Koerber, Steven C.; Rivier, Jean

doi:10.1255/ejms.436

Cited by 2 publications

(1 citation statement)

References 19 publications

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“…17 Tandem mass spectrometry(MS/MS) is becoming the useful method for the identification of rearrangement phenomenon due to its reliability, sensitivity and speed. 18,19 Several studies have reported unusual fragmentation patterns for N-phosphoryl amino acids and peptide derivatives by using ESI-MS/MS. 20,21 In this paper, stepwise fragmentations of N-phosphoryl dipeptide methyl ester using electrospray ionization (ESI) tandem mass spectrometry (MS/MS) were studied.…”

Section: Introductionmentioning

confidence: 99%

Characterization of Electrospray Ionization Mass Spectrometry for N-Diisopropyloxyphosphoryl Dipeptide Methyl Esters

Luo

Niu

et al. 2005

Eur J Mass Spectrom (Chichester)

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A systematic study of the fragmentation pattern of N-diisopropyloxyphosphoryl (DIPP) dipeptide methyl esters in an electrospray ionization (ESI) tandem mass spectrometry (MS/MS) was presented. A combination of accurate mass measurement and tandem mass spectrometry had been used to characterize the major fragment ions observed in the ESI mass spectrum. It was found that the alkali metal ions acted as a fixed charge site and expelled the DIPP group after transferring a proton to the amide nitrogen. For all the N-phosphoryl dipeptide methyl esters, under the activation of a metal ion, the rearrangement product ion at m/z 163 was observed and confirmed to be the sodium adduct of phosphoric acid mono-isopropyl esters (PAIE), via a specific five-membered penta-co-ordinated phosphorus intermediate. However, no rearrangement ion was observed when a beta-amino acid was at the N-terminal. This could be used to develop a novel method for differentiating isomeric compounds when either alpha- or beta-amino acid are at the N-terminus of peptides. From the [M+Na]+ ESI-MS/MS spectra of N-phosphoryl dipeptide methyl esters (DIPP Xaa1 Xaa2 OMe), the peaks corresponding to the [M+Na Xaa1 C3H6]+ were observed and explained. The [M+Na]+ ESI-MS/MS spectra of N-phosphoryl dipeptide methyl esters with Phe located in the C-terminal, such as DIPPValPheOMe, DIPPLeuPheOMe, DIPPIlePheOMe, DIPPAlaPheOMe and DIPPPhePheOMe, had characteristic fragmentation. Two unusual gas-phase intramolecular rearrangement mechanisms were first proposed for this fragmentation. These rearrangements were not observed in dipeptide methyl ester analogs which did not contain the DIPP at the N-terminal, suggesting that this moiety was critical for the rearrangement.

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Section: Introductionmentioning

confidence: 99%

Characterization of Electrospray Ionization Mass Spectrometry for N-Diisopropyloxyphosphoryl Dipeptide Methyl Esters

Luo

Niu

et al. 2005

Eur J Mass Spectrom (Chichester)

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2002

J. Mass Spectrom.

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In order to keep subscribers up‐to‐date with the latest developments in their field, John Wiley & Sons are providing a current awareness service in each issue of the journal. The bibliography contains newly published material in the field of mass spectrometry. Each bibliography is divided into 11 sections: 1 Books, Reviews & Symposia; 2 Instrumental Techniques & Methods; 3 Gas Phase Ion Chemistry; 4 Biology/Biochemistry: Amino Acids, Peptides & Proteins; Carbohydrates; Lipids; Nucleic Acids; 5 Pharmacology/Toxicology; 6 Natural Products; 7 Analysis of Organic Compounds; 8 Analysis of Inorganics/Organometallics; 9 Surface Analysis; 10 Environmental Analysis; 11 Elemental Analysis. Within each section, articles are listed in alphabetical order with respect to author (3 Weeks journals ‐ Search completed at 2nd. Jan. 2002)

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Characterization of Betidamino Acid-Containing Somatostatin and Gonadotropin-Releasing Hormone Analogs with Electrospray Mass Spectrometry and Tandem Mass Spectrometry

Cited by 2 publications

References 19 publications

Characterization of Electrospray Ionization Mass Spectrometry for N-Diisopropyloxyphosphoryl Dipeptide Methyl Esters

Characterization of Electrospray Ionization Mass Spectrometry for N-Diisopropyloxyphosphoryl Dipeptide Methyl Esters

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