Fast-atom bombardment and tandem mass spectrometry of macrolide antibiotics

Ronald Cerny, Denise K. MacMillan, Michael L. Gross, Alan K. Mallams, Birendra N. Pramanik

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Molecular weights of macrolide antibiotics can be determined from either (M + H)+ or (M + Met)+, the latter desorbed from alkali metal salt-saturated matrices. The ion chemistry of macrolides, as determined by tandem mass spectrometry (MS/MS), is different for ions produced as metallated than those formed as (M + H)+ species. An explanation for these differences is the location of the charge. For protonated species, the charge is most likely situated on a functional group with high proton affinity, such as the dimethylamino group of the ammo sugar. The alkali metal ion, however, is bonded to the highly oxygenated aglycone. As a result, the collision-activated dissociation spectra of protonated macrolides are simple with readily identifiable fragment ions in both the high and low mass regions but no fragments in the middle mass range. In contrast, the cationized species give complex spectra with many abundant ions, most of which are located in the high mass range. The complementary nature of the fragmentation of these two species recommends the study of both by MS/MS when determining the structure or confirming the identity of these biomaterials.

Original languageEnglish (US)
Pages (from-to)151-158
Number of pages8
JournalJournal of the American Society for Mass Spectrometry
Volume5
Issue number3
DOIs
StatePublished - Mar 1994

Fingerprint

Fast Atom Bombardment Mass Spectrometry
Macrolides
Tandem Mass Spectrometry
Mass spectrometry
Ions
Anti-Bacterial Agents
Alkali Metals
Atoms
Biocompatible Materials
Sugars
Functional groups
Metal ions
Protons
Salts
Molecular weight
Molecular Weight

ASJC Scopus subject areas

  • Structural Biology
  • Spectroscopy

Cite this

Fast-atom bombardment and tandem mass spectrometry of macrolide antibiotics. / Cerny, Ronald; MacMillan, Denise K.; Gross, Michael L.; Mallams, Alan K.; Pramanik, Birendra N.

In: Journal of the American Society for Mass Spectrometry, Vol. 5, No. 3, 03.1994, p. 151-158.

Research output: Contribution to journalArticle

Cerny, Ronald ; MacMillan, Denise K. ; Gross, Michael L. ; Mallams, Alan K. ; Pramanik, Birendra N. / Fast-atom bombardment and tandem mass spectrometry of macrolide antibiotics. In: Journal of the American Society for Mass Spectrometry. 1994 ; Vol. 5, No. 3. pp. 151-158.
@article{bab594ed8af44bc19a35e5c9b2794e6e,
title = "Fast-atom bombardment and tandem mass spectrometry of macrolide antibiotics",
abstract = "Molecular weights of macrolide antibiotics can be determined from either (M + H)+ or (M + Met)+, the latter desorbed from alkali metal salt-saturated matrices. The ion chemistry of macrolides, as determined by tandem mass spectrometry (MS/MS), is different for ions produced as metallated than those formed as (M + H)+ species. An explanation for these differences is the location of the charge. For protonated species, the charge is most likely situated on a functional group with high proton affinity, such as the dimethylamino group of the ammo sugar. The alkali metal ion, however, is bonded to the highly oxygenated aglycone. As a result, the collision-activated dissociation spectra of protonated macrolides are simple with readily identifiable fragment ions in both the high and low mass regions but no fragments in the middle mass range. In contrast, the cationized species give complex spectra with many abundant ions, most of which are located in the high mass range. The complementary nature of the fragmentation of these two species recommends the study of both by MS/MS when determining the structure or confirming the identity of these biomaterials.",
author = "Ronald Cerny and MacMillan, {Denise K.} and Gross, {Michael L.} and Mallams, {Alan K.} and Pramanik, {Birendra N.}",
year = "1994",
month = "3",
doi = "10.1016/1044-0305(94)85028-3",
language = "English (US)",
volume = "5",
pages = "151--158",
journal = "Journal of the American Society for Mass Spectrometry",
issn = "1044-0305",
publisher = "Springer New York",
number = "3",

}

TY - JOUR

T1 - Fast-atom bombardment and tandem mass spectrometry of macrolide antibiotics

AU - Cerny, Ronald

AU - MacMillan, Denise K.

AU - Gross, Michael L.

AU - Mallams, Alan K.

AU - Pramanik, Birendra N.

PY - 1994/3

Y1 - 1994/3

N2 - Molecular weights of macrolide antibiotics can be determined from either (M + H)+ or (M + Met)+, the latter desorbed from alkali metal salt-saturated matrices. The ion chemistry of macrolides, as determined by tandem mass spectrometry (MS/MS), is different for ions produced as metallated than those formed as (M + H)+ species. An explanation for these differences is the location of the charge. For protonated species, the charge is most likely situated on a functional group with high proton affinity, such as the dimethylamino group of the ammo sugar. The alkali metal ion, however, is bonded to the highly oxygenated aglycone. As a result, the collision-activated dissociation spectra of protonated macrolides are simple with readily identifiable fragment ions in both the high and low mass regions but no fragments in the middle mass range. In contrast, the cationized species give complex spectra with many abundant ions, most of which are located in the high mass range. The complementary nature of the fragmentation of these two species recommends the study of both by MS/MS when determining the structure or confirming the identity of these biomaterials.

AB - Molecular weights of macrolide antibiotics can be determined from either (M + H)+ or (M + Met)+, the latter desorbed from alkali metal salt-saturated matrices. The ion chemistry of macrolides, as determined by tandem mass spectrometry (MS/MS), is different for ions produced as metallated than those formed as (M + H)+ species. An explanation for these differences is the location of the charge. For protonated species, the charge is most likely situated on a functional group with high proton affinity, such as the dimethylamino group of the ammo sugar. The alkali metal ion, however, is bonded to the highly oxygenated aglycone. As a result, the collision-activated dissociation spectra of protonated macrolides are simple with readily identifiable fragment ions in both the high and low mass regions but no fragments in the middle mass range. In contrast, the cationized species give complex spectra with many abundant ions, most of which are located in the high mass range. The complementary nature of the fragmentation of these two species recommends the study of both by MS/MS when determining the structure or confirming the identity of these biomaterials.

UR - http://www.scopus.com/inward/record.url?scp=0000602662&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0000602662&partnerID=8YFLogxK

U2 - 10.1016/1044-0305(94)85028-3

DO - 10.1016/1044-0305(94)85028-3

M3 - Article

C2 - 24222544

AN - SCOPUS:0000602662

VL - 5

SP - 151

EP - 158

JO - Journal of the American Society for Mass Spectrometry

JF - Journal of the American Society for Mass Spectrometry

SN - 1044-0305

IS - 3

ER -