{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,9]],"date-time":"2026-10-09T19:57:49Z","timestamp":1791575869102,"version":"4.3.4"},"reference-count":42,"publisher":"Wiley","issue":"5","license":[{"start":{"date-parts":[[2009,1,8]],"date-time":"2009-01-08T00:00:00Z","timestamp":1231372800000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["J. Mass Spectrom."],"published-print":{"date-parts":[[2009,5]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>\n                    Structure elucidation of tertiary or quaternary protein structures by chemical cross\u2010linking and mass spectrometry (MS) has recently gained importance. To locate the cross\u2010linker modification, dedicated software is applied to analyze the mass or tandem mass spectra (MS\/MS). Such software requires information on target amino acids to limit the data analysis time. The most commonly used homobifunctional N\u2010hydroxy succinimide (NHS) esters are often described as reactive exclusively towards primary amines, although side reactions with tyrosine and serine have been reported. Our goal was to systematically study the reactivity of NHS esters and derive some general rules for their attack of nucleophilic amino acid side chains in peptides. We therefore studied the cross\u2010linking reactions of synthesized and commercial model peptides with disuccinimidyl suberate (DSS). The first reaction site in all cases was expectedly the \u03b1\u2010NH\n                    <jats:sub>2<\/jats:sub>\n                    \u2010group of the\n                    <jats:italic>N<\/jats:italic>\n                    \u2010terminus or the \u03b5\u2010NH\n                    <jats:sub>2<\/jats:sub>\n                    \u2010group of lysine. As soon as additional cross\u2010linkers were attached or loops were formed, other amino acids were also involved in the reaction. In addition to the primary amino groups, serine, threonine and tyrosine showed significant reactivity due to the effect of neighboring amino acids by intermediate or permanent Type\u20101 cross\u2010link formation. The reactivity is highly dependent on the pH and on adjacent amino acids. Copyright \u00a9 2009 John Wiley &amp; Sons, Ltd.\n                  <\/jats:p>","DOI":"10.1002\/jms.1544","type":"journal-article","created":{"date-parts":[[2009,1,8]],"date-time":"2009-01-08T07:58:13Z","timestamp":1231401493000},"page":"694-706","source":"Crossref","is-referenced-by-count":302,"title":["Chemical cross\u2010linking with NHS esters: a systematic study on amino acid reactivities"],"prefix":"10.1002","volume":"44","author":[{"given":"Stefanie","family":"M\u00e4dler","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Claudia","family":"Bich","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"David","family":"Touboul","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Renato","family":"Zenobi","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2009,1,8]]},"reference":[{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac0519108"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1002\/bms.1200201209"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1002\/(SICI)1096-9888(199808)33:8<697::AID-JMS711>3.0.CO;2-H"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1002\/jms.1280"},{"key":"e_1_2_6_6_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2005.07.020"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi010259"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1255\/ejms.748"},{"key":"e_1_2_6_9_2","doi-asserted-by":"publisher","DOI":"10.1021\/bi036149f"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1073\/pnas.090099097"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1002\/mas.20082"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/rcm.885"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1255\/ejms.590"},{"key":"e_1_2_6_14_2","doi-asserted-by":"publisher","DOI":"10.1016\/S1044-0305(03)00327-1"},{"key":"e_1_2_6_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/pr060154z"},{"key":"e_1_2_6_16_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac001379a"},{"key":"e_1_2_6_17_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jasms.2006.04.020"},{"key":"e_1_2_6_18_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0968-0004(01)01954-5"},{"key":"e_1_2_6_19_2","unstructured":"S.Wefing V.Schnaible D.Hoffmann.SearchXLinks http:\/\/www.searchxlinks.de\/. 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