Formylation of His Residues at Position 2 in Peptide b Ions due to Noncanonical C α ‐CO Bond Cleavage: Assignment of the m/z 166 Product Ion in Proteome Data Article Swipe
Sanjeev Kumar
,
Marimuthu Vijayasarathy
,
Manjunath A. Venkatesha
,
P. Balaram
·
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/rcm.10154
YOU?
·
· 2025
· Open Access
·
· DOI: https://doi.org/10.1002/rcm.10154
Rationale The low m/z region (less than 300) in the MS/MS spectra of peptides is rich with product ions arising from neutral losses and noncanonical bond cleavages, resulting from the gas‐phase chemistry of low mass b n / y n ions containing reactive side chains. This study explores the ion chemistry arising from the presence of His residues at the N‐terminus of peptides, focusing on the product ion at m/z 166 often designated as His‐related ion . Methods Tandem mass spectrometry analysis of model His containing synthetic di and tripeptides was carried out on an ion‐trap mass spectrometer. Isotope labelling ( 13 C ) of the residue(1) CO group permitted monitoring the fate of the labelled carbon atom. A dataset of tryptic peptides containing the m/z 166 ion in their MS/MS spectra was extracted from the consensus human‐HCD proteome data available from the NIST database. Results MS/MS analysis of the tripeptide Ala‐His‐Ala‐amide (AHA*), together with isotopically labelled analogs N α ‐formyl histidyl ion (fH) amide and synthetic N α ‐formyl His amide establishes that the product ion at m/z 166.061 corresponds to the protonated form of the N α ‐formyl histidyl ion. Studies with 13 C labelled LH amide confirm fH arises by C α ‐CO bond cleavage in the XH b 2 ion. Proteomic data analysis confirms that this unusual cleavage is widely observed in tryptic peptides. Examination of the top 500 peptides based on intensity of m/z 166 revealed that the overwhelming majority contain N‐terminus XH motifs. Examinations of the top 100 sequences from a dataset of 6064 peptides lacking His that yielded m/z 166 revealed that the majority of 85 sequences arise from AQ b 2 ions by neutral loss of 2NH 3 . Conclusions In peptide sequences containing N‐terminus XH motifs, the histidine imidazole side chain facilitates C α ‐CO bond cleavage at residue X.
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Formylation of His Residues at Position 2 in Peptide b Ions due to Noncanonical C α ‐CO Bond Cleavage: Assignment of the m/z 166 Product Ion in Proteome DataWork title
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2025-10-23Full publication date if available
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Sanjeev Kumar, Marimuthu Vijayasarathy, Manjunath A. Venkatesha, P. BalaramList of authors in order
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| abstract_inverted_index.model | 84 |
| abstract_inverted_index.often | 72 |
| abstract_inverted_index.study | 47 |
| abstract_inverted_index.their | 130 |
| abstract_inverted_index.‐CO | 206, 304 |
| abstract_inverted_index.Tandem | 79 |
| abstract_inverted_index.arises | 202 |
| abstract_inverted_index.carbon | 117 |
| abstract_inverted_index.losses | 23 |
| abstract_inverted_index.region | 5 |
| abstract_inverted_index.widely | 224 |
| abstract_inverted_index.(AHA*), | 153 |
| abstract_inverted_index.166.061 | 180 |
| abstract_inverted_index.Isotope | 99 |
| abstract_inverted_index.Methods | 78 |
| abstract_inverted_index.Results | 146 |
| abstract_inverted_index.Studies | 193 |
| abstract_inverted_index.analogs | 158 |
| abstract_inverted_index.arising | 20, 52 |
| abstract_inverted_index.carried | 92 |
| abstract_inverted_index.chains. | 45 |
| abstract_inverted_index.confirm | 200 |
| abstract_inverted_index.contain | 246 |
| abstract_inverted_index.dataset | 120, 258 |
| abstract_inverted_index.lacking | 262 |
| abstract_inverted_index.motifs, | 295 |
| abstract_inverted_index.motifs. | 249 |
| abstract_inverted_index.neutral | 22, 282 |
| abstract_inverted_index.peptide | 290 |
| abstract_inverted_index.product | 18, 67, 176 |
| abstract_inverted_index.residue | 308 |
| abstract_inverted_index.spectra | 12, 132 |
| abstract_inverted_index.tryptic | 122, 227 |
| abstract_inverted_index.unusual | 221 |
| abstract_inverted_index.yielded | 265 |
| abstract_inverted_index.ABSTRACT | 0 |
| abstract_inverted_index.analysis | 82, 148, 217 |
| abstract_inverted_index.cleavage | 208, 222, 306 |
| abstract_inverted_index.confirms | 218 |
| abstract_inverted_index.explores | 48 |
| abstract_inverted_index.focusing | 64 |
| abstract_inverted_index.histidyl | 162, 191 |
| abstract_inverted_index.labelled | 116, 157, 197 |
| abstract_inverted_index.majority | 245, 271 |
| abstract_inverted_index.observed | 225 |
| abstract_inverted_index.peptides | 14, 123, 234, 261 |
| abstract_inverted_index.presence | 55 |
| abstract_inverted_index.proteome | 139 |
| abstract_inverted_index.reactive | 43 |
| abstract_inverted_index.residues | 58 |
| abstract_inverted_index.revealed | 241, 268 |
| abstract_inverted_index.together | 154 |
| abstract_inverted_index.Proteomic | 215 |
| abstract_inverted_index.Rationale | 1 |
| abstract_inverted_index.available | 141 |
| abstract_inverted_index.chemistry | 32, 51 |
| abstract_inverted_index.consensus | 137 |
| abstract_inverted_index.database. | 145 |
| abstract_inverted_index.extracted | 134 |
| abstract_inverted_index.histidine | 297 |
| abstract_inverted_index.imidazole | 298 |
| abstract_inverted_index.intensity | 237 |
| abstract_inverted_index.labelling | 100 |
| abstract_inverted_index.peptides, | 63 |
| abstract_inverted_index.peptides. | 228 |
| abstract_inverted_index.permitted | 110 |
| abstract_inverted_index.resulting | 28 |
| abstract_inverted_index.sequences | 255, 274, 291 |
| abstract_inverted_index.synthetic | 87, 167 |
| abstract_inverted_index.‐formyl | 161, 170, 190 |
| abstract_inverted_index.cleavages, | 27 |
| abstract_inverted_index.containing | 42, 86, 124, 292 |
| abstract_inverted_index.designated | 73 |
| abstract_inverted_index.ion‐trap | 96 |
| abstract_inverted_index.monitoring | 111 |
| abstract_inverted_index.protonated | 184 |
| abstract_inverted_index.residue(1) | 107 |
| abstract_inverted_index.tripeptide | 151 |
| abstract_inverted_index.Conclusions | 288 |
| abstract_inverted_index.Examination | 229 |
| abstract_inverted_index.corresponds | 181 |
| abstract_inverted_index.establishes | 173 |
| abstract_inverted_index.facilitates | 301 |
| abstract_inverted_index.gas‐phase | 31 |
| abstract_inverted_index.human‐HCD | 138 |
| abstract_inverted_index.tripeptides | 90 |
| abstract_inverted_index.Examinations | 250 |
| abstract_inverted_index.N‐terminus | 61, 247, 293 |
| abstract_inverted_index.isotopically | 156 |
| abstract_inverted_index.noncanonical | 25 |
| abstract_inverted_index.overwhelming | 244 |
| abstract_inverted_index.spectrometry | 81 |
| abstract_inverted_index.His‐related | 75 |
| abstract_inverted_index.spectrometer. | 98 |
| abstract_inverted_index.Ala‐His‐Ala‐amide | 152 |
| cited_by_percentile_year | |
| corresponding_author_ids | https://openalex.org/A5065728901 |
| countries_distinct_count | 1 |
| institutions_distinct_count | 4 |
| corresponding_institution_ids | https://openalex.org/I11947397, https://openalex.org/I194223965 |
| citation_normalized_percentile.value | 0.53575864 |
| citation_normalized_percentile.is_in_top_1_percent | False |
| citation_normalized_percentile.is_in_top_10_percent | False |