2004
DOI: 10.1002/jms.557
|View full text |Cite
|
Sign up to set email alerts
|

Rearrangement process occurring in the fragmentation of adefovir derivatives

Abstract: The fragmentation of the antiviral drug adefovir dipivoxil and its two active metabolites, adefovir and monopivoxil adefovir, was investigated using both ion trap and triple-quadrupole mass spectrometers. Fragment ions due to loss of 30 Da were observed and attributed to an unanticipated rearrangement process by loss of formaldehyde. The proposed mechanism is supported with the aid of three newly synthesized adefovir derivatives and with accurate mass measurement. Other fragmentations by loss of a pivaloyl gro… Show more

Help me understand this report

Search citation statements

Order By: Relevance

Paper Sections

Select...
1
1
1
1

Citation Types

2
9
0

Year Published

2004
2004
2014
2014

Publication Types

Select...
8

Relationship

3
5

Authors

Journals

citations
Cited by 11 publications
(11 citation statements)
references
References 13 publications
2
9
0
Order By: Relevance
“…2c). The proposed fragmentation of cPr-PMEDAP and PMEDAP is in accordance with that described previously for adefovir (25). Two minor peaks were also found in the chromatograms, but no deamination to PMEG was observed (Fig.…”
Section: Identification Of N-dealkylation Of Cpr-pmedapsupporting
confidence: 87%
“…2c). The proposed fragmentation of cPr-PMEDAP and PMEDAP is in accordance with that described previously for adefovir (25). Two minor peaks were also found in the chromatograms, but no deamination to PMEG was observed (Fig.…”
Section: Identification Of N-dealkylation Of Cpr-pmedapsupporting
confidence: 87%
“…These ions have all lost the units H and I, and, in addition, a HN¢C¢O group (m/z 1109), the carbamate group (NH 2 COOH) from unit F (m/z 1091), a HN¢C¢O as well as the PO 3 H group (m/z 1029), or the whole uronamide-derived unit F (m/z 902). The formation of the latter ion by an internal residue loss requires a rearrangement reaction, which has been described for several compounds [42][43][44][45][46]. One possible structure of the ion at m/z 902, which is an alternative to the one proposed by Eichhorn and Aga [6], is given in Scheme observed in the intensity-range below 1% of the base peak, but still with a good S/N ratio ( Figure 2b and Scheme 2).…”
Section: Maldi-it/rtof-msmentioning
confidence: 70%
“…1a). The formation pathways of these fragment ions have been reported in the literature [19]. The fragment ion at m/z 162.0 formed by breaking the single carbon-oxygen bond in the side chain was present in the highest abundance.…”
Section: Development Of Mass Spectrometrymentioning
confidence: 88%