title: Collision-induced dissociation fragmentation inside disulfide C-terminal loops of natural non-tryptic peptides.
abstract: Collision-induced dissociation (CID) spectra of long non-tryptic peptides are usually quite complicated and rather difficult to interpret. Disulfide bond formed by two cysteine residues at C-terminus of frog skin peptides precludes one to determine sequence inside the forming loop. Thereby, chemical modification of S-S bonds is often used in "bottom up" sequencing approach. However, low-energy CID spectra of natural non-tryptic peptides with C-terminal disulfide cycle demonstrate an unusual fragmentation route, which may be used to elucidate the "hidden" C-terminal sequence. Low charge state protonated molecules experience peptide bond cleavage at the N-terminus of C-terminal cysteine. The forming isomeric acyclic ions serve as precursors for a series of b-type ions revealing sequence inside former disulfide cycle. The reaction is preferable for peptides with basic lysine residues inside the cycle. It may also be activated by acidic protons of Asp and Glu residues neighboring the loop. The observed cleavages may be quite competitive, revealing the sequence inside disulfide cycle, although S-S bond rupture does not occur in this case.
authors: Department of Chemistry, M.V. Lomonosov Moscow State University, Moscow, Russian Federation.
authors: Tatiana Y
authors: TY
authors: Samgina
authors: Egor A
authors: EA
authors: Vorontsov
authors: Vladimir A
authors: VA
authors: Gorshkov
authors: Konstantin A
authors: KA
authors: Artemenko
authors: Roman A
authors: RA
authors: Zubarev
authors: Jimmy A
authors: JA
authors: Ytterberg
authors: Albert T
authors: AT
authors: Lebedev
mesh_terms: D000595:Amino Acid Sequence; D029845:Amphibian Proteins / Q000737:chemistry / Q000235:genetics / Q000378:metabolism; D000818:Animals; D004220:Disulfides / Q000737:chemistry; D013058:Mass Spectrometry / Q000379:methods*; D008969:Molecular Sequence Data; D010446:Peptide Fragments / Q000737:chemistry; D010455:Peptides / Q000737:chemistry*; D011499:Protein Processing, Post-Translational; D011898:Ranidae / Q000235:genetics / Q000502:physiology; D020539:Sequence Analysis, Protein; D012867:Skin / Q000737:chemistry / Q000378:metabolism
chemical_list: D029845:Amphibian Proteins; D004220:Disulfides; D010446:Peptide Fragments; D010455:Peptides
references: J Am Chem Soc. 2003 Mar 19;125(11):3353-69
references: 12630891
references: Eur J Mass Spectrom (Chichester). 2012;18(4):345-8
references: 22971694
references: Rapid Commun Mass Spectrom. 2005;19(21):3063-74
references: 16200662
references: Anal Chem. 1998 Jan 1;70(1):136-43
references: 9435472
references: Anal Biochem. 1992 Mar;201(2):216-26
references: 1632509
references: J Mass Spectrom. 2010 Dec;45(12):1477-82
references: 21031361
references: J Proteome Res. 2002 Nov-Dec;1(6):549-57
references: 12645623
references: Rapid Commun Mass Spectrom. 2009 May;23(9):1241-8
references: 19308951
references: Angew Chem Int Ed Engl. 2005 Oct 7;44(39):6399-403
references: 16173101
references: J Biol Chem. 2012 Jan 6;287(2):1510-9
references: 22117064
references: J Agric Food Chem. 2012 Apr 11;60(14):3708-16
references: 22439977
references: J Am Chem Soc. 2003 Jul 23;125(29):8949-58
references: 12862492
references: Rapid Commun Mass Spectrom. 2007;21(21):3420-6
references: 17902199
references: J Proteomics. 2012 Oct 22;75(18):5807-21
references: 22917879
references: Mass Spectrom Rev. 2002 May-Jun;21(3):183-216
references: 12476442
references: Anal Bioanal Chem. 2008 Nov;392(5):831-8
references: 18663433
references: Rapid Commun Mass Spectrom. 2008 Nov;22(22):3517-25
references: 18855342
references: Anal Chem. 2011 Apr 15;83(8):3133-40
references: 21428412
references: J Am Soc Mass Spectrom. 2012 Feb;23(2):310-20
references: 22161508
references: Anal Chem. 2006 Jul 15;78(14):4820-9
references: 16841900
references: Eur J Mass Spectrom (Chichester). 2007;13(2):155-63
references: 17881782
references: J Mass Spectrom. 2000 Dec;35(12):1399-406
references: 11180630
references: Mass Spectrom Rev. 2009 Jan-Feb;28(1):20-34
references: 18989895
references: J Am Soc Mass Spectrom. 2007 Jun;18(6):1109-23
references: 17462910
references: Anal Chem. 2010 Oct 1;82(19):8313-9
references: 20843009
references: J Pharmacol Toxicol Methods. 1992 Dec;28(4):199-200
references: 1296824
references: Mass Spectrom Rev. 2002 Mar-Apr;21(2):87-107
references: 12373746
references: Eur J Mass Spectrom (Chichester). 2011;17(1):73-83
references: 21625031