Collision-induced dissociation of noncovalent complexes between vancomycin antibiotics and peptide ligand stereoisomers: Evidence for molecular recognition in the gas phase

被引:58
作者
Jorgensen, TJD
Delforge, D
Remacle, J
Bojesen, G
Roepstorff, P
机构
[1] Odense Univ, Dept Mol Biol, DK-5230 Odense M, Denmark
[2] Fac Univ Notre Dame Paix, Biochim Cellulaire Lab, B-5000 Namur, Belgium
[3] Univ Copenhagen, HC Orsted Inst, Dept Chem, DK-2100 Copenhagen O, Denmark
关键词
mass spectrometry; noncovalent complexes; glycopeptide antibiotics; molecular recognition; electrospray ionization; collision-induced dissociation;
D O I
10.1016/S1387-3806(98)14282-3
中图分类号
O64 [物理化学(理论化学)、化学物理学]; O56 [分子物理学、原子物理学];
学科分类号
070203 ; 070304 ; 081704 ; 1406 ;
摘要
In solution, the antibiotics of the vancomycin group bind stereospecifically to peptides with the C-terminal sequence: -L-Lys-D-Ala-D-Ala, Substitution by a L-Ala at either of the two C-terminal residues causes a dramatic decrease in the binding affinity to the antibiotics. This solution behavior is clearly reflected in electrospray ionization (ESI) mass spectra obtained from equimolar mixtures of an antibiotic, an isotopically labelled peptide ligand and an unlabelled peptide stereoisomer. Using collision-induced dissociation (CID) we have probed the gas phase stability of isomeric (1:1) noncovalent complexes formed between vancomycin and tripeptide stereoisomers. In negative ion mode the CID results show that a complex formed between vancomycin and a -L-Ala-L-Ala ligand fragments more readily than a complex formed between vancomycin and a -D-Ala-D-Ala ligand. This difference in gas phase stability is in agreement with what would be expected if the noncovalent complexes had retained their structural specific interactions from solution to gas phase. In positive ion mode no significant difference in the gas phase stabilities of the isomeric complexes could be observed. We attribute this similarity in gas phase stability between isomeric positively-charged complexes to a protonation of the C-terminus of the peptide ligand which destroys the specific interaction between antibiotic and peptide ligand. Molecular recognition phenomena in the gas phase were investigated by CID of mixed cluster ions consisting of an antibiotic, a -L-Ala peptide, a -D-Ala stereoisomer, one ligand isotopically labelled. Upon CID of the negatively charged mixed cluster ions a stereoselective loss of the assumed "nonspecifically" bound -L-Ala ligand was observed. (Int J Mass Spectrom 188 (1999) 63-85) (C) 1999 Elsevier Science B.V.
引用
收藏
页码:63 / 85
页数:23
相关论文
共 49 条
[11]   THE USE OF TRIPLE QUADRUPOLES FOR SEQUENTIAL MASS-SPECTROMETRY .2. A DETAILED CASE-STUDY [J].
DAWSON, PH ;
FRENCH, JB ;
BUCKLEY, JA ;
DOUGLAS, DJ ;
SIMMONS, D .
ORGANIC MASS SPECTROMETRY, 1982, 17 (05) :212-219
[12]   Solid-phase synthesis of tailed cyclic peptides: The use of alpha-allyl-protected aspartic acid leads to aspartimide and tetramethylguanidinium formation [J].
Delforge, D ;
Dieu, M ;
Delaive, E ;
Art, M ;
Gillon, B ;
Devreese, B ;
Raes, M ;
VanBeeumen, J ;
Remacle, J .
LETTERS IN PEPTIDE SCIENCE, 1996, 3 (02) :89-97
[13]   THE ROLE OF THE SUGAR AND CHLORINE SUBSTITUENTS IN THE DIMERIZATION OF VANCOMYCIN ANTIBIOTICS [J].
GERHARD, U ;
MACKAY, JP ;
MAPLESTONE, RA ;
WILLIAMS, DH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (01) :232-237
[14]   Dissociation of heme-globin complexes by blackbody infrared radiative dissociation: Molecular specificity in the gas phase? [J].
Gross, DS ;
Zhao, YX ;
Williams, ER .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 1997, 8 (05) :519-524
[15]   EXPRESSION OF ELECTROSTATIC BINDING COOPERATIVITY IN THE RECOGNITION OF CELL-WALL PEPTIDE ANALOGS BY VANCOMYCIN GROUP ANTIBIOTICS [J].
GROVES, P ;
SEARLE, MS ;
WESTWELL, MS ;
WILLIAMS, DH .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1994, (13) :1519-1520
[16]   INVESTIGATION OF COMPLEXES BETWEEN SOME GLYCOPEPTIDE ANTIBIOTICS AND BACTERIAL CELL-WALL ANALOGS BY ELECTROSPRAY-MASS-SPECTROMETRY AND CAPILLARY-ZONE-ELECTROPHORESIS/ELECTROSPRAY-MASS-SPECTROMETRY [J].
HAMDAN, M ;
CURCURUTO, O ;
DIMODUGNO, E .
RAPID COMMUNICATIONS IN MASS SPECTROMETRY, 1995, 9 (10) :883-887
[17]  
JORGENSEN TG, UNPUB
[18]   Direct determination of solution binding constants for noncovalent complexes between bacterial cell wall peptide analogues and vancomycin group antibiotics by electrospray ionization mass spectrometry [J].
Jorgensen, TJD ;
Roepstorff, P ;
Heck, AJR .
ANALYTICAL CHEMISTRY, 1998, 70 (20) :4427-4432
[19]   COLOR TEST FOR DETECTION OF FREE TERMINAL AMINO GROUPS IN SOLID-PHASE SYNTHESIS OF PEPTIDES [J].
KAISER, E ;
COLESCOT.RL ;
BOSSINGE.CD ;
COOK, PI .
ANALYTICAL BIOCHEMISTRY, 1970, 34 (02) :595-&
[20]   A DIRECT COMPARISON OF FIRST AND 2ND GAS-PHASE BASICITIES OF THE OCTAPEPTIDE RPPGFSPF [J].
KALTASHOV, IA ;
FENSELAU, CC .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (39) :9906-9910