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Electrospray ionization tandem mass spectrometry of protonated and alkali-cationized Boc-N-protected hybrid peptides containing repeats of D-Ala-APyC and APyC-D-Ala: Formation of [b(n-1)  + OCH(3)  + Na](+) and [b(n-1)  + OH + Na](+) ions.
MedLine Citation:
PMID:  23059875     Owner:  NLM     Status:  In-Data-Review    
Abstract/OtherAbstract:
RATIONALE: Differentiation and structural characterization of positional isomers of non-natural amino acid hybrid peptides by using electrospray ionization tandem mass spectrometry (ESI-MS(n) ) is desirable because of their fundamental importance from the view point of peptide mass spectrometry and also of their increasing importance in the area of research towards biomedical and material applications; hence, the present study is undertaken.
METHODS: Electrospray ionization ion-trap tandem mass spectrometry (ESI-MS(n) ) was used to characterize and differentiate three pairs of positional isomers of Boc-N-protected hybrid peptides containing repeats of D-Ala-APyC and APyC-D-Ala (D-Ala = D-alanine and APyC = trans-3-aminopyran-2-carboxylic acid).
RESULTS: ESI-MS(n) spectra of protonated and alkali-cationized positional isomeric peptides display characteristic fragmentation involving the peptide backbone, the Boc group, and the side chain. It is observed that abundant rearrangement ions [b(n-1)  + OCH(3)  + Na](+) or [b(n-1)  + OH + Na](+) are formed when D-Ala is present at C-terminus and the presence of APyC at the C-terminus inhibits the formation of rearrangement ions. In addition, abundant b(n-1) (+) ions are formed, presumably with stable oxazolone structures, when the C-terminus of b(n-1) (+) ions possessed D-Ala.
CONCLUSIONS: The present study demonstrates that ESI tandem mass spectrometry is very useful for differentiating positional isomers of hybrid peptides containing D-Ala and APyC amino acids. While the protonated peptides give rise to characteristic sequencing ions, the cationized peptides produce additional rearrangement ions ([b(n-1)  + OCH(3)  + Na](+) and [b(n-1)  + OH + Na](+) ) which helps distinguish between the presence of D-Ala and APyC amino acids at the C-terminus. Copyright © 2012 John Wiley & Sons, Ltd.
Authors:
G Raju; C Purna Chander; K Srinivas Reddy; R Srinivas; G V M Sharma
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Publication Detail:
Type:  Journal Article    
Journal Detail:
Title:  Rapid communications in mass spectrometry : RCM     Volume:  26     ISSN:  1097-0231     ISO Abbreviation:  Rapid Commun. Mass Spectrom.     Publication Date:  2012 Nov 
Date Detail:
Created Date:  2012-10-12     Completed Date:  -     Revised Date:  -    
Medline Journal Info:
Nlm Unique ID:  8802365     Medline TA:  Rapid Commun Mass Spectrom     Country:  England    
Other Details:
Languages:  eng     Pagination:  2591-600     Citation Subset:  IM    
Copyright Information:
Copyright © 2012 John Wiley & Sons, Ltd.
Affiliation:
National Centre for Mass Spectrometry, CSIR - Indian Institute of Chemical Technology, Hyderabad, 500 007, India.
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