{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,17]],"date-time":"2026-08-17T14:37:15Z","timestamp":1786977435984,"version":"build-2736575974"},"reference-count":29,"publisher":"Wiley","issue":"7","license":[{"start":{"date-parts":[[2012,4,13]],"date-time":"2012-04-13T00:00:00Z","timestamp":1334275200000},"content-version":"vor","delay-in-days":0,"URL":"http:\/\/onlinelibrary.wiley.com\/termsAndConditions#vor"}],"content-domain":{"domain":["chemistry-europe.onlinelibrary.wiley.com"],"crossmark-restriction":true},"short-container-title":["ChemBioChem"],"published-print":{"date-parts":[[2012,5,7]]},"DOI":"10.1002\/cbic.201200035","type":"journal-article","created":{"date-parts":[[2012,4,13]],"date-time":"2012-04-13T16:29:14Z","timestamp":1334334554000},"page":"987-991","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":16,"title":["Use of a Multicomponent Reaction for Chemoselective Derivatization of Multiple Classes of Metabolites"],"prefix":"10.1002","volume":"13","author":[{"given":"Kyle A.","family":"Totaro","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Babajide O.","family":"Okandeji","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Jason K.","family":"Sello","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2012,4,13]]},"reference":[{"key":"e_1_2_4_1_2","unstructured":"\u00a0"},{"key":"e_1_2_4_2_2","first-page":"285","volume":"25","author":"Dunn W. B.","year":"2005","journal-title":"TrAC, TrAC Trends Anal. Chem."},{"key":"e_1_2_4_3_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.jchromb.2008.04.031"},{"key":"e_1_2_4_4_2","doi-asserted-by":"publisher","DOI":"10.1021\/cb900271r"},{"key":"e_1_2_4_5_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.aca.2009.11.042"},{"key":"e_1_2_4_6_2","doi-asserted-by":"publisher","DOI":"10.1021\/ac100331b"},{"key":"e_1_2_4_7_2","doi-asserted-by":"publisher","DOI":"10.1007\/s11481-009-9156-4"},{"key":"e_1_2_4_8_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmeth.1549"},{"key":"e_1_2_4_9_2","doi-asserted-by":"publisher","DOI":"10.1038\/nchembio.186"},{"key":"e_1_2_4_10_2","doi-asserted-by":"publisher","DOI":"10.1093\/jxb\/eri069"},{"key":"e_1_2_4_11_2","volume-title":"Handbook of Derivatization Reactions for HPLC","author":"Lunn G.","year":"1998"},{"key":"e_1_2_4_12_2","doi-asserted-by":"publisher","DOI":"10.1038\/nmeth1038"},{"key":"e_1_2_4_13_2","unstructured":"\u00a0"},{"key":"e_1_2_4_14_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000915)112:18<3300::AID-ANGE3300>3.0.CO;2-Z"},{"key":"e_1_2_4_14_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U"},{"key":"e_1_2_4_15_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr0505728"},{"key":"e_1_2_4_16_2","doi-asserted-by":"publisher","DOI":"10.1016\/0040-4020(96)00647-3"},{"key":"e_1_2_4_17_2","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3757(20000616)112:12<2202::AID-ANGE2202>3.0.CO;2-6"},{"key":"e_1_2_4_17_3","doi-asserted-by":"publisher","DOI":"10.1002\/1521-3773(20000616)39:12<2109::AID-ANIE2109>3.0.CO;2-9"},{"key":"e_1_2_4_18_2","doi-asserted-by":"publisher","DOI":"10.1021\/ja038583a"},{"key":"e_1_2_4_19_2","doi-asserted-by":"publisher","DOI":"10.1021\/ar00022a001"},{"key":"e_1_2_4_20_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0040-4020(99)00388-9"},{"key":"e_1_2_4_21_2","unstructured":"In reactions of aspartic acid and glutamic acid the \u03b1\u2010amino acid moieties participate in a Ugi 4\u2010component 5\u2010center reaction while the carboxylate side chain participated in a Passerini reaction. This is a so\u2010called tandem Ugi\u2013Passerini reaction."},{"key":"e_1_2_4_22_2","unstructured":"Except for reactions with tryptophan tyrosine and serine our yields are higher than those reported by Ugi. In the aforementioned cases Ugi included triethylamine presumably to enhance the nucleophilicity of methanol. These findings imply that these reactions need not be performed at \u221230\u2009\u00b0C."},{"key":"e_1_2_4_23_2","unstructured":"Arginine's basic guanidinium group facilitates solvolytic cleavage of the isocyanide carbamate yielding a methyl carbamate. The poor solubility of cysteine in methanol and acetonitrile precludes efficient reaction."},{"key":"e_1_2_4_24_2","unstructured":"Benzylamine 4\u2010pentenoic acid and\/or isobutyraldehyde were selected for use as the other U\u20104CR substrates in these derivatization experiments."},{"key":"e_1_2_4_25_2","doi-asserted-by":"publisher","DOI":"10.1016\/j.tetlet.2008.05.073"},{"key":"e_1_2_4_26_2","doi-asserted-by":"publisher","DOI":"10.1021\/ol061605o"},{"key":"e_1_2_4_27_2","doi-asserted-by":"publisher","DOI":"10.1093\/ajcn\/42.2.361"}],"container-title":["ChemBioChem"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.wiley.com\/onlinelibrary\/tdm\/v1\/articles\/10.1002%2Fcbic.201200035","content-type":"unspecified","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/pdf\/10.1002\/cbic.201200035","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,12]],"date-time":"2025-10-12T19:35:31Z","timestamp":1760297731000},"score":1,"resource":{"primary":{"URL":"https:\/\/chemistry-europe.onlinelibrary.wiley.com\/doi\/10.1002\/cbic.201200035"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2012,4,13]]},"references-count":29,"journal-issue":{"issue":"7","published-print":{"date-parts":[[2012,5,7]]}},"alternative-id":["10.1002\/cbic.201200035"],"URL":"https:\/\/doi.org\/10.1002\/cbic.201200035","archive":["Portico"],"relation":{},"ISSN":["1439-4227","1439-7633"],"issn-type":[{"value":"1439-4227","type":"print"},{"value":"1439-7633","type":"electronic"}],"subject":[],"published":{"date-parts":[[2012,4,13]]},"assertion":[{"value":"2012-01-13","order":0,"name":"received","label":"Received","group":{"name":"publication_history","label":"Publication History"}},{"value":"2012-04-13","order":3,"name":"published","label":"Published","group":{"name":"publication_history","label":"Publication History"}}]}}