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A widely applied chemistry, and one for which many reagents are available, is reaction of the activated ester of a carboxylic acid (often a succinimidyl ester) with amino groups at mildly basic pH. Reductive alkylation using a carbonyl compound and a hydride\u2010donating reducing agent is another valued reaction with multiple applications. Most proteins contain more than one amino group, so the extent of reaction desired must be considered in advance and the result assessed experimentally after the fact. The distinctive environment of the \u03b1\u2010amino group of a polypeptide sets it apart from the \u025b\u2010amino groups of lysine side chains, and can afford useful specificity. \u00a9 2016 by John Wiley &amp; Sons, Inc.<\/jats:p>","DOI":"10.1002\/cpps.17","type":"journal-article","created":{"date-parts":[[2016,11,1]],"date-time":"2016-11-01T08:10:36Z","timestamp":1477987836000},"source":"Crossref","is-referenced-by-count":8,"title":["Modification of Amino Groups"],"prefix":"10.1002","volume":"86","author":[{"given":"Kieran F.","family":"Geoghegan","sequence":"first","affiliation":[{"name":"Structural Biology and Biophysics, Pfizer Worldwide Research  Groton Connecticut"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"311","published-online":{"date-parts":[[2016,11]]},"reference":[{"key":"e_1_2_8_2_1_1","doi-asserted-by":"publisher","DOI":"10.1385\/1-59259-169-8:459"},{"key":"e_1_2_8_2_2_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc00034a015"},{"key":"e_1_2_8_2_3_1","doi-asserted-by":"publisher","DOI":"10.1110\/ps.8.4.921"},{"key":"e_1_2_8_2_4_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2013.121"},{"key":"e_1_2_8_2_5_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja00741a013"},{"key":"e_1_2_8_2_6_1","doi-asserted-by":"publisher","DOI":"10.1039\/jr9630002918"},{"key":"e_1_2_8_2_7_1","doi-asserted-by":"publisher","DOI":"10.1002\/bit.22921"},{"key":"e_1_2_8_2_8_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc300594y"},{"key":"e_1_2_8_2_9_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc950074d"},{"key":"e_1_2_8_2_10_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc00015a010"},{"key":"e_1_2_8_2_11_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc00014a008"},{"key":"e_1_2_8_2_12_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1998.2990"},{"key":"e_1_2_8_2_13_1","doi-asserted-by":"publisher","DOI":"10.1007\/s00216\u2010008\u20102231\u20105"},{"key":"e_1_2_8_2_14_1","doi-asserted-by":"publisher","DOI":"10.1038\/nmeth1008\u2010853"},{"key":"e_1_2_8_2_15_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0169\u2010409X(02)00023\u20106"},{"key":"e_1_2_8_2_16_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5CS00048C"},{"key":"e_1_2_8_2_17_1","doi-asserted-by":"publisher","DOI":"10.1134\/S0003683815070030"},{"key":"e_1_2_8_2_18_1","doi-asserted-by":"publisher","DOI":"10.1021\/acs.bioconjchem.5b00457"},{"key":"e_1_2_8_2_19_1","doi-asserted-by":"publisher","DOI":"10.1038\/nprot.2013.168"},{"key":"e_1_2_8_2_20_1","doi-asserted-by":"publisher","DOI":"10.1021\/pr9002382"},{"key":"e_1_2_8_2_21_1","doi-asserted-by":"publisher","DOI":"10.1002\/jctb.4556"},{"key":"e_1_2_8_2_22_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc700306n"},{"key":"e_1_2_8_2_23_1","doi-asserted-by":"publisher","DOI":"10.1038\/msb.2012.31"},{"key":"e_1_2_8_2_24_1","doi-asserted-by":"publisher","DOI":"10.1039\/C5SC00408J"},{"key":"e_1_2_8_2_25_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.ab.2009.09.027"},{"key":"e_1_2_8_2_26_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja509955n"},{"key":"e_1_2_8_2_27_1","doi-asserted-by":"publisher","DOI":"10.1021\/bi062142x"},{"key":"e_1_2_8_2_28_1","doi-asserted-by":"publisher","DOI":"10.1016\/S0022\u20101759(02)00039\u2010X"},{"key":"e_1_2_8_2_29_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja802495w"},{"key":"e_1_2_8_2_30_1","doi-asserted-by":"publisher","DOI":"10.1038\/ncomms5740"},{"key":"e_1_2_8_2_31_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.tibs.2012.02.003"},{"key":"e_1_2_8_2_32_1","doi-asserted-by":"publisher","DOI":"10.1002\/jms.1415"},{"key":"e_1_2_8_2_33_1","first-page":"189","volume-title":"Methods in Molecular Biology","author":"Tan K.","year":"2014"},{"key":"e_1_2_8_2_34_1","doi-asserted-by":"publisher","DOI":"10.1021\/ja2055098"},{"key":"e_1_2_8_2_35_1","doi-asserted-by":"publisher","DOI":"10.1016\/j.str.2006.09.005"},{"key":"e_1_2_8_2_36_1","doi-asserted-by":"publisher","DOI":"10.1021\/bc00002a005"},{"key":"e_1_2_8_2_37_1","doi-asserted-by":"publisher","DOI":"10.1002\/9780470559277.ch100018"},{"key":"e_1_2_8_2_38_1","doi-asserted-by":"publisher","DOI":"10.1006\/abio.1996.0011"},{"key":"e_1_2_8_2_39_1","doi-asserted-by":"publisher","DOI":"10.1021\/BC980120K"},{"key":"e_1_2_8_3_2_1","unstructured":"Koniev O.andWagner A.2015. 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