{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,10,26]],"date-time":"2025-10-26T10:43:34Z","timestamp":1761475414099,"version":"build-2065373602"},"reference-count":29,"publisher":"Wiley","issue":"9","license":[{"start":{"date-parts":[[2013,4,15]],"date-time":"2013-04-15T00:00:00Z","timestamp":1365984000000},"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":[[2013,5,15]]},"abstract":"<jats:sec>\n                    <jats:title>RATIONALE<\/jats:title>\n                    <jats:p>\n                      Glycophthalocyanines have a great promising potential in many scientific areas. However, their structural characterization is not an easy task. To overcome this drawback, it is urgent to develop simple and efficient methodologies to characterize this type of compounds. In this work, we describe the use of matrix\u2010assisted laser desorption\/ionization mass spectrometry (MALDI\u2010MS) and MALDI\u2010MS\/MS of the [M+H]\n                      <jats:sup>+<\/jats:sup>\n                      to distinguish between two isomeric glycophatholocyanines bearing four galactose units with protected (\n                      <jats:bold>1a<\/jats:bold>\n                      and\n                      <jats:bold>2a<\/jats:bold>\n                      ) or unprotected hydroxyl groups (\n                      <jats:bold>1b<\/jats:bold>\n                      and\n                      <jats:bold>2b<\/jats:bold>\n                      ).\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>METHODS<\/jats:title>\n                    <jats:p>The MALDI\u2010MS and MALDI\u2010MS\/MS spectra were acquired using a MALDI\u2010TOF\/TOF Applied Biosystems 4800 Proteomics Analyzer instrument equipped with a nitrogen laser and using dithranol as matrix. Computational studies were performed in order to gain insights into the mechanisms underlying the different fragmentation pathways observed for the isomeric species.<\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>RESULTS<\/jats:title>\n                    <jats:p>\n                      The fragmentation pattern observed in MALDI\u2010MS\/MS spectra of the [M+H]\n                      <jats:sup>+<\/jats:sup>\n                      ion was dependent on the peripheral distribution of the sugar units. Phthalocyanines (Pcs) with a sugar unit in each isoindole ring show the typical loss of sugar units (cleavage of C6\u2013O bond) while Pcs with the four sugar units linked to the same isoindole ring show a major and unusual fragmentation pathway corresponding to the cleavage of the C5\u2013C6 bond of the sugar units. This type of fragmentation is not usually observed in the MS\/MS of oligosaccharides.\n                    <\/jats:p>\n                  <\/jats:sec>\n                  <jats:sec>\n                    <jats:title>CONCLUSIONS<\/jats:title>\n                    <jats:p>MALDI\u2013MS is a valuable tool for the structural characterization\/differentiation of isomeric glycophthalocyanines. Copyright \u00a9 2013 John Wiley &amp; Sons, Ltd.<\/jats:p>\n                  <\/jats:sec>","DOI":"10.1002\/rcm.6533","type":"journal-article","created":{"date-parts":[[2013,4,17]],"date-time":"2013-04-17T01:19:33Z","timestamp":1366161573000},"page":"1019-1026","source":"Crossref","is-referenced-by-count":3,"title":["Glycophthalocyanines: structural differentiation and isomeric differentiation by matrix\u2010assisted laser desorption\/ionization tandem mass spectrometry"],"prefix":"10.1002","volume":"27","author":[{"given":"Ana R. M.","family":"Soares","sequence":"first","affiliation":[{"name":"Department of Chemistry and QOPNA University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"Maria G. P. M. S.","family":"Neves","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"S\u00e9rgio M.","family":"Santos","sequence":"additional","affiliation":[{"name":"Department of Chemistry and CICECO University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"Jo\u00e3o P. C.","family":"Tom\u00e9","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"Augusto C.","family":"Tom\u00e9","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"Jos\u00e9 A. S.","family":"Cavaleiro","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA University of Aveiro  3810\u2010193 Aveiro Portugal"}]},{"given":"Tom\u00e1s","family":"Torres","sequence":"additional","affiliation":[{"name":"Department of Organic Chemistry University Autonoma of Madrid  Cantoblanco 28049 Madrid Spain"},{"name":"IMDEA Nanociencia Facultad de Ciencias  Cantoblanco 28049 Madrid Spain"}]},{"given":"M. Ros\u00e1rio M.","family":"Domingues","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA University of Aveiro  3810\u2010193 Aveiro Portugal"}]}],"member":"311","published-online":{"date-parts":[[2013,4,15]]},"reference":[{"volume-title":"The Porphyrin Handbook","year":"2003","author":"Kadish K.M.","key":"e_1_2_6_2_1"},{"key":"e_1_2_6_3_1","doi-asserted-by":"publisher","DOI":"10.1039\/B614234F"},{"key":"e_1_2_6_4_1","doi-asserted-by":"publisher","DOI":"10.1201\/9781482296952"},{"key":"e_1_2_6_5_1","doi-asserted-by":"publisher","DOI":"10.1002\/chem.201103516"},{"key":"e_1_2_6_6_1","doi-asserted-by":"publisher","DOI":"10.1021\/jm300398q"},{"key":"e_1_2_6_7_1","doi-asserted-by":"publisher","DOI":"10.1039\/c1cc13783b"},{"key":"e_1_2_6_8_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ccr.2010.05.002"},{"key":"e_1_2_6_9_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2004.12.137"},{"key":"e_1_2_6_10_1","doi-asserted-by":"publisher","DOI":"10.1039\/b822128f"},{"key":"e_1_2_6_11_1","doi-asserted-by":"publisher","DOI":"10.1142\/S1088424612300030"},{"key":"e_1_2_6_12_1","first-page":"3097","article-title":"Synthesis of octaglycosylated zinc(II) phthalocyanines","author":"Iqbal Z.","year":"2010","journal-title":"Synthesis"},{"key":"e_1_2_6_13_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.carres.2008.12.009"},{"key":"e_1_2_6_14_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2006.10.155"},{"key":"e_1_2_6_15_1","doi-asserted-by":"publisher","DOI":"10.1007\/7081_2007_056"},{"key":"e_1_2_6_16_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ijms.2005.03.001"},{"key":"e_1_2_6_17_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.reactfunctpolym.2005.02.007"},{"key":"e_1_2_6_18_1","first-page":"371","volume-title":"The Porphyrin Handbook","author":"Quirke J. 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