{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,1,5]],"date-time":"2026-01-05T22:13:54Z","timestamp":1767651234170,"version":"build-2065373602"},"reference-count":45,"publisher":"Wiley","issue":"1","license":[{"start":{"date-parts":[[2012,12,12]],"date-time":"2012-12-12T00:00:00Z","timestamp":1355270400000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Rapid Comm Mass Spectrometry"],"published-print":{"date-parts":[[2013,1,15]]},"abstract":"<jats:sec>\n                    <jats:title>RATIONALE<\/jats:title>\n                    <jats:p>It has been shown that the disulfide moiety in the chemical cross\u2010linking reagent dithiobis(succinimidyl)propionate (DSP), which is similar in structure to the natural cystine disulfide, cleaves preferentially to the peptide backbone in the negative ion mode. However, the tandem mass (MS\/MS) spectra of peptides in the negative ion mode are often dominated by products arising from low\u2010energy, side\u2010chain\u2010induced processes, which may compete with any facile cross\u2010linker fragmentations and complicate identification of chemical cross\u2010links in a complex mixture.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>METHODS<\/jats:title>\n                    <jats:p>Two disulfide\u2010containing crosslinking reagents similar to DSP, but with varying spacer arm lengths, were synthesized and the MS\/MS spectra of several model peptides cross\u2010linked with these reagents were investigated. Theoretical calculations were used to describe the energetics of the cross\u2010linker fragmentations as well as several low\u2010energy side\u2010chain\u2010induced fragmentations which compete with disulfide cleavages.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>RESULTS<\/jats:title>\n                    <jats:p>Altering the spacer arm length of the cross\u2010linker, such that there is one methylene group less than in DSP, results in a more facile cleavage process, whilst the opposite is true when a methylene group is added. Of the low\u2010energy side\u2010chain\u2010induced fragmentations studied, only those from aspartic acid compete significantly with those of the cross\u2010linker disulfide.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>CONCLUSIONS<\/jats:title>\n                    <jats:p>Low\u2010energy cleavage processes from aspartic acid that compete with cross\u2010linker fragmentations occur in the negative ion MS\/MS spectra of the cross\u2010linked peptides, irrespective of the spacer arm length. Other fragmentation pathways do not significantly interfere with low\u2010energy disulfide cleavage, making the presence of additional product ions in the MS\/MS spectrum diagnostic for the presence of aspartic acid. Copyright \u00a9 2012 John Wiley &amp; Sons, Ltd.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.6445","type":"journal-article","created":{"date-parts":[[2012,12,13]],"date-time":"2012-12-13T11:41:55Z","timestamp":1355398915000},"page":"238-248","source":"Crossref","is-referenced-by-count":7,"title":["Negative ion fragmentations of disulfide\u2010containing cross\u2010linking reagents are competitive with aspartic acid side\u2010chain\u2010induced cleavages"],"prefix":"10.1002","volume":"27","author":[{"given":"Antonio N.","family":"Calabrese","sequence":"first","affiliation":[{"name":"School of Chemistry and Physics The University of Adelaide  Adelaide SA Australia 5005"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tianfang","family":"Wang","sequence":"additional","affiliation":[{"name":"School of Chemistry and Physics The University of Adelaide  Adelaide SA Australia 5005"},{"name":"School of Science, Education and Engineering The University of the Sunshine Coast  Sippy Downs Qld Australia 4556"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"John H.","family":"Bowie","sequence":"additional","affiliation":[{"name":"School of Chemistry and Physics The University of Adelaide  Adelaide SA Australia 5005"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Tara L.","family":"Pukala","sequence":"additional","affiliation":[{"name":"School of Chemistry and Physics The University of Adelaide  Adelaide SA Australia 5005"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"311","published-online":{"date-parts":[[2012,12,12]]},"reference":[{"key":"e_1_2_6_2_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-009-3405-5"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1002\/mas.20082"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1074\/mcp.R000001-MCP201"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jsb.2010.10.014"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1002\/mas.20293"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1074\/mcp.M700274-MCP200"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2005.07.020"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2004.02.008"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/pr900257z"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1002\/cbic.200700150"},{"key":"e_1_2_6_12_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac900853k"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac0488762"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja026917a"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja0614159"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1074\/jbc.M207370200"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1074\/mcp.T400016-MCP200"},{"key":"e_1_2_6_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac0257492"},{"key":"e_1_2_6_19_1","doi-asserted-by":"publisher","DOI":"10.1002\/prot.21445"},{"key":"e_1_2_6_20_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2006.04.020"},{"key":"e_1_2_6_21_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac101241t"},{"key":"e_1_2_6_22_1","doi-asserted-by":"publisher","DOI":"10.1074\/mcp.M110.002212"},{"key":"e_1_2_6_23_1","doi-asserted-by":"publisher","DOI":"10.1016\/S1044-0305(00)00212-9"},{"key":"e_1_2_6_24_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac0613840"},{"key":"e_1_2_6_25_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.3213"},{"key":"e_1_2_6_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac702277q"},{"key":"e_1_2_6_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac801625e"},{"key":"e_1_2_6_28_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac800625x"},{"key":"e_1_2_6_29_1","doi-asserted-by":"publisher","DOI":"10.1007\/s13361-012-0407-x"},{"key":"e_1_2_6_30_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.2872"},{"key":"e_1_2_6_31_1","doi-asserted-by":"publisher","DOI":"10.1002\/mas.20206"},{"key":"e_1_2_6_32_1","doi-asserted-by":"publisher","DOI":"10.1039\/c0cp00717j"},{"key":"e_1_2_6_33_1","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.2149"},{"key":"e_1_2_6_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ac060132w"},{"key":"e_1_2_6_35_1","doi-asserted-by":"publisher","DOI":"10.1002\/mas.10022"},{"key":"e_1_2_6_36_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216-008-2231-5"},{"key":"e_1_2_6_37_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2010.04.004"},{"key":"e_1_2_6_38_1","doi-asserted-by":"publisher","DOI":"10.1063\/1.464913"},{"key":"e_1_2_6_39_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.cplett.2004.06.011"},{"key":"e_1_2_6_40_1","doi-asserted-by":"publisher","DOI":"10.1021\/j100096a001"},{"volume-title":"Gaussian 09, Revision B.01","year":"2009","author":"Frisch M. 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