Backbone cleavages of [M - H](-) anions of peptides. Cyclisation of citropin 1 peptides involving reactions between the C-terminal [CONH](-) residue and backbone amide carbonyl groups. A new type of beta cleavage: a joint experimental and theoretical study

Rapid Communications in Mass Spectrometry : RCM
Craig S BrinkworthJohn H Bowie

Abstract

This paper reports the study of backbone cleavages in the collision-induced negative-ion mass spectra of the [M - H](-) anions of some synthetic modifications of the bioactive amphibian peptide citropin 1 (GLFDVIKKVASVIGGL-NH(2)). The peptides chosen for study contain no amino acid residues which could effect facile side-chain cleavage, i.e. Ser (-CH(2)O, side-chain cleavage) and Asp (-H(2)O) are replaced by Ala or Lys. We expected that such peptides should exhibit standard and pronounced peaks due to alpha cleavage ions (and to a lesser extent beta cleavage ions) in their collision-induced negative-ion spectra. This expectation was realised, but the spectra also contained peaks formed by a new series of cleavage anions. These are produced following cyclisation of the C-terminal CONH(-) moiety at carbonyl functions of amide groups along the peptide backbone; effectively transferring the NH of the C-terminal CONH(-) group to other amino acid residues. We have called the product anions of these processes beta' ions, in order to distinguish them from standard beta ions. Some beta' ions also fragment directly to some other beta' ions of smaller mass. The reaction coordinates of alpha,beta and beta' backbone processes have been calc...Continue Reading

References

Jan 1, 1983·Methods in Enzymology·M W HunkapillerL E Hood
Jan 1, 1995·Rapid Communications in Mass Spectrometry : RCM·A M BradfordJ H Bowie
Feb 27, 1999·International Journal for Parasitology·J E Frisch
Oct 12, 2001·Rapid Communications in Mass Spectrometry : RCM·C S BrinkworthJ H Bowie
Jan 30, 2002·Rapid Communications in Mass Spectrometry : RCM·Pinmanee BoontheungRussell V Baudinette

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Citations

Apr 8, 2011·Journal of the American Society for Mass Spectrometry·Brad J WilliamsDavid H Russell
Jul 27, 2012·Journal of the American Society for Mass Spectrometry·Samantha S Bokatzian-JohnsonCarolyn J Cassady
Feb 10, 2009·Journal of the American Society for Mass Spectrometry·Suman S Thakur, Padmanabhan Balaram
Dec 7, 2007·Rapid Communications in Mass Spectrometry : RCM·Dan Pu, Carolyn J Cassady
Jul 11, 2012·Rapid Communications in Mass Spectrometry : RCM·Tianfang WangJohn H Bowie
Jul 22, 2015·The Journal of Physical Chemistry. B·Chelsea E PlummerCarolyn J Cassady
Jul 12, 2002·Journal of Mass Spectrometry : JMS

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