{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,31]],"date-time":"2026-10-31T11:21:30Z","timestamp":1793445690346,"version":"4.5.0"},"reference-count":37,"publisher":"Springer Science and Business Media LLC","issue":"1","license":[{"start":{"date-parts":[[2018,11,5]],"date-time":"2018-11-05T00:00:00Z","timestamp":1541376000000},"content-version":"tdm","delay-in-days":0,"URL":"http:\/\/www.springer.com\/tdm"}],"content-domain":{"domain":["link.springer.com"],"crossmark-restriction":false},"short-container-title":["Nature Chem"],"published-print":{"date-parts":[[2019,1]]},"DOI":"10.1038\/s41557-018-0154-0","type":"journal-article","created":{"date-parts":[[2018,10,29]],"date-time":"2018-10-29T10:17:18Z","timestamp":1540808238000},"page":"78-85","update-policy":"https:\/\/doi.org\/10.1007\/springer_crossmark_policy","source":"Crossref","is-referenced-by-count":93,"title":["A chemoselective strategy for late-stage functionalization of complex small molecules with polypeptides and proteins"],"prefix":"10.1038","volume":"11","author":[{"given":"Daniel T.","family":"Cohen","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Chi","family":"Zhang","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Colin M.","family":"Fadzen","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Alexander J.","family":"Mijalis","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Liana","family":"Hie","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Kenneth D.","family":"Johnson","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zachary","family":"Shriver","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Obadiah","family":"Plante","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-7817-1318","authenticated-orcid":false,"given":"Scott J.","family":"Miller","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Stephen L.","family":"Buchwald","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Bradley L.","family":"Pentelute","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"297","published-online":{"date-parts":[[2018,11,5]]},"reference":[{"key":"154_CR1","doi-asserted-by":"publisher","first-page":"174","DOI":"10.1016\/j.cbpa.2015.08.005","volume":"28","author":"PM Drake","year":"2015","unstructured":"Drake, P. M. & Rabuka, D. An emerging playbook for antibody\u2013drug conjugates: lessons from the laboratory and clinic suggest a strategy for improving efficacy and safety. Curr. Opin. Chem. Biol. 28, 174\u2013180 (2015).","journal-title":"Curr. Opin. Chem. Biol."},{"key":"154_CR2","doi-asserted-by":"publisher","first-page":"2053","DOI":"10.1016\/j.bbapap.2014.06.008","volume":"1844","author":"T Ueda","year":"2014","unstructured":"Ueda, T. Next-generation optimized biotherapeutics\u2014a review and preclinical study. Biochim. Biophys. Acta 1844, 2053\u20132057 (2014).","journal-title":"Biochim. Biophys. Acta"},{"key":"154_CR3","doi-asserted-by":"publisher","first-page":"47","DOI":"10.1021\/bc010021y","volume":"13","author":"PR Hamann","year":"2002","unstructured":"Hamann, P. R. et al. Gemtuzumab ozogamicin, a potent and selective anti-CD33 antibody\u2013calicheamicin conjugate for treatment of acute myeloid leukemia. Bioconjug. Chem. 13, 47\u201358 (2002).","journal-title":"Bioconjug. Chem."},{"key":"154_CR4","doi-asserted-by":"publisher","first-page":"2436","DOI":"10.1110\/ps.051478705","volume":"14","author":"L Wang","year":"2005","unstructured":"Wang, L., Amphlett, G., Bl\u00e4ttler, W. A., Lambert, J. M. & Zhang, W. Structural characterization of the maytansinoid\u2013monoclonal antibody immunoconjugate, huN901\u2013DM1, by mass spectrometry. Protein Sci. 14, 2436\u20132446 (2005).","journal-title":"Protein Sci."},{"key":"154_CR5","doi-asserted-by":"publisher","first-page":"9280","DOI":"10.1158\/0008-5472.CAN-08-1776","volume":"68","author":"GD Lewis Phillips","year":"2008","unstructured":"Lewis Phillips, G. D. et al. Targeting HER2-positive breast cancer with trastuzumab\u2013DM1, an antibody\u2013cytotoxic drug conjugate. Cancer Res. 68, 9280\u20139290 (2008).","journal-title":"Cancer Res."},{"key":"154_CR6","doi-asserted-by":"publisher","first-page":"925","DOI":"10.1038\/nbt.1480","volume":"26","author":"JR Junutula","year":"2008","unstructured":"Junutula, J. R. et al. Site-specific conjugation of a cytotoxic drug to an antibody improves the therapeutic index. Nat. Biotechnol. 26, 925\u2013932 (2008).","journal-title":"Nat. Biotechnol."},{"key":"154_CR7","doi-asserted-by":"publisher","first-page":"1994","DOI":"10.1021\/bc200212a","volume":"22","author":"CA Boswell","year":"2011","unstructured":"Boswell, C. A. et al. Impact of drug conjugation on pharmacokinetics and tissue distribution of anti-STEAP1 antibody\u2013drug conjugates in rats. Bioconjug. Chem. 22, 1994\u20132004 (2011).","journal-title":"Bioconjug. Chem."},{"key":"154_CR8","doi-asserted-by":"publisher","first-page":"7890","DOI":"10.1021\/jm500552c","volume":"57","author":"TH Pillow","year":"2014","unstructured":"Pillow, T. H. et al. Site-specific trastuzumab maytansinoid antibody\u2013drug conjugates with improved therapeutic activity through linker and antibody engineering. J. Med. Chem. 57, 7890\u20137899 (2014).","journal-title":"J. Med. Chem."},{"key":"154_CR9","doi-asserted-by":"publisher","first-page":"2954","DOI":"10.1039\/C6SC00170J","volume":"7","author":"P Akkapeddi","year":"2016","unstructured":"Akkapeddi, P. et al. Construction of homogeneous antibody\u2013drug conjugates using site-selective protein chemistry. Chem. Sci. 7, 2954\u20132963 (2016).","journal-title":"Chem. Sci."},{"key":"154_CR10","doi-asserted-by":"publisher","first-page":"11307","DOI":"10.1039\/c2cc36711d","volume":"48","author":"LH Zou","year":"2012","unstructured":"Zou, L.-H., Reball, J., Mottweiler, J. & Bolm, C. Transition metal-free direct C\u2013H bond thiolation of 1,3,4-oxadiazoles and related heteroarenes. Chem. Commun. 48, 11307\u201311309 (2012).","journal-title":"Chem. Commun."},{"key":"154_CR11","doi-asserted-by":"publisher","first-page":"3898","DOI":"10.1021\/acs.orglett.5b01889","volume":"17","author":"T Hostier","year":"2015","unstructured":"Hostier, T., Ferey, V., Ricci, G., Gomez Pardo, D. & Cossy, J. Synthesis of aryl sulfides: metal-free C\u2013H sulfenylation of electron-rich arenes. Org. Lett. 17, 3898\u20133901 (2015).","journal-title":"Org. Lett."},{"key":"154_CR12","doi-asserted-by":"publisher","first-page":"8999","DOI":"10.1021\/jo2017444","volume":"76","author":"S Ranjit","year":"2011","unstructured":"Ranjit, S. et al. Copper-mediated C\u2013H activation\/C\u2013S cross-coupling of heterocycles with thiols. J. Org. Chem. 76, 8999\u20139007 (2011).","journal-title":"J. Org. Chem."},{"key":"154_CR13","doi-asserted-by":"publisher","first-page":"4183","DOI":"10.1055\/s-0029-1217605","volume":"2009","author":"XL Fang","year":"2009","unstructured":"Fang, X.-L., Tang, R.-Y., Zhong, P. & Li, J.-H. Iron-catalyzed sulfenylation of indoles with disulfides promoted by a catalytic amount of iodine. Synthesis 2009, 4183\u20134189 (2009).","journal-title":"Synthesis"},{"key":"154_CR14","doi-asserted-by":"publisher","first-page":"9784","DOI":"10.1021\/jacs.5b05447","volume":"137","author":"DT Cohen","year":"2015","unstructured":"Cohen, D. T., Zhang, C., Pentelute, B. L. & Buchwald, S. L. An umpolung approach for the chemoselective arylation of selenocysteine in unprotected peptides. J. Am. Chem. Soc. 137, 9784\u20139787 (2015).","journal-title":"J. Am. Chem. Soc."},{"key":"154_CR15","unstructured":"Hall, D. G. in Boronic Acids: Preparation and Applications in Organic Synthesis and Medicine (ed. Hall, D. G.) Ch. 1 (Wiley, Hoboken, 2006)."},{"key":"154_CR16","doi-asserted-by":"publisher","first-page":"1227","DOI":"10.1128\/AAC.34.6.1227","volume":"34","author":"PM Small","year":"1990","unstructured":"Small, P. M. & Chambers, H. F. Vancomycin for Staphylococcus aureus endocarditis in intravenous drug users. Antimicrob. Agents Chemother. 34, 1227\u20131231 (1990).","journal-title":"Antimicrob. Agents Chemother."},{"key":"154_CR17","doi-asserted-by":"publisher","first-page":"686","DOI":"10.1128\/CMR.13.4.686","volume":"13","author":"Y Cetinkaya","year":"2000","unstructured":"Cetinkaya, Y., Falk, P. & Mayhall, C. G. Vancomycin-resistant enterococci. Clin. Microbiol. Rev. 13, 686\u2013707 (2000).","journal-title":"Clin. Microbiol. Rev."},{"key":"154_CR18","doi-asserted-by":"publisher","first-page":"689","DOI":"10.1128\/AAC.46.3.689-694.2002","volume":"46","author":"S Navon-Venezia","year":"2002","unstructured":"Navon-Venezia, S., Feder, R., Gaidukov, L., Carmeli, Y. & Mor, A. Antibacterial properties of dermaseptin S4 derivatives with in vivo activity. Antimicrob. Agents Chemother. 46, 689\u2013694 (2002).","journal-title":"Antimicrob. Agents Chemother."},{"key":"154_CR19","doi-asserted-by":"publisher","first-page":"e26727","DOI":"10.1371\/journal.pone.0026727","volume":"6","author":"NY Yount","year":"2011","unstructured":"Yount, N. Y. et al. Context mediates antimicrobial efficacy of kinocidin congener peptide RP-1. PLoS One 6, e26727 (2011).","journal-title":"PLoS One"},{"key":"154_CR20","doi-asserted-by":"publisher","first-page":"939","DOI":"10.1038\/nrmicro1789","volume":"5","author":"L Dijkshoorn","year":"2007","unstructured":"Dijkshoorn, L., Nemec, A. & Seifert, H. An increasing threat in hospitals: multidrug-resistant Acinetobacter baumannii. Nat. Rev. Microbiol. 5, 939\u2013951 (2007).","journal-title":"Nat. Rev. Microbiol."},{"key":"154_CR21","doi-asserted-by":"publisher","first-page":"363","DOI":"10.1016\/j.ijantimicag.2012.01.018","volume":"39","author":"MK O\u2019Shea","year":"2012","unstructured":"O\u2019Shea, M. K. Acinetobacter in modern warfare. Int. J. Antimicrob. Agents 39, 363\u2013375 (2012).","journal-title":"Int. J. Antimicrob. Agents"},{"key":"154_CR22","doi-asserted-by":"publisher","first-page":"1254","DOI":"10.1086\/529198","volume":"46","author":"LL Maragakis","year":"2008","unstructured":"Maragakis, L. L. & Perl, T. M. Acinetobacter baumannii: epidemiology, antimicrobial resistance, and treatment options. Clin. Infect. Dis. 46, 1254\u20131263 (2008).","journal-title":"Clin. Infect. Dis."},{"key":"154_CR23","doi-asserted-by":"publisher","first-page":"2040","DOI":"10.1021\/jm950750x","volume":"39","author":"I Andreadou","year":"1996","unstructured":"Andreadou, I., Menge, W. M. P. B., Commandeur, J. N. M., Worthington, E. A. & Vermeulen, N. P. E. Synthesis of novel Se-substituted selenocysteine derivatives as potential kidney selective prodrugs of biologically active selenol compounds: evaluation of kinetics of \u03b2-elimination reactions in rat renal cytosol. J. Med. Chem. 39, 2040\u20132046 (1996).","journal-title":"J. Med. Chem."},{"key":"154_CR24","doi-asserted-by":"publisher","first-page":"278","DOI":"10.1016\/S0041-008X(96)80034-2","volume":"141","author":"I Andreadou","year":"1996","unstructured":"Andreadou, I., van de Water, B., Commandeur, J. N., Nagelkerke, F. J. & Vermeulen, N. P. Comparative cytotoxicity of 14 novel selenocysteine Se-conjugates in rat renal proximal tubular cells. Toxicol. Appl. Pharmacol. 141, 278\u2013287 (1996).","journal-title":"Toxicol. Appl. Pharmacol."},{"key":"154_CR25","doi-asserted-by":"publisher","first-page":"45","DOI":"10.1016\/0891-5849(94)90007-8","volume":"17","author":"JE Spallholz","year":"1994","unstructured":"Spallholz, J. E. On the nature of selenium toxicity and carcinostatic activity. Free Radic. Biol. Med. 17, 45\u201364 (1994).","journal-title":"Free Radic. Biol. Med."},{"key":"154_CR26","doi-asserted-by":"publisher","first-page":"2670","DOI":"10.1016\/j.febslet.2010.04.014","volume":"584","author":"J L\u00f6fblom","year":"2010","unstructured":"L\u00f6fblom, J. et al. Affibody molecules: engineered proteins for therapeutic, diagnostic and biotechnological applications. FEBS Lett. 584, 2670\u20132680 (2010).","journal-title":"FEBS Lett."},{"key":"154_CR27","doi-asserted-by":"publisher","first-page":"4339","DOI":"10.1158\/0008-5472.CAN-05-3521","volume":"66","author":"A Orlova","year":"2006","unstructured":"Orlova, A. et al. Tumor imaging using a picomolar affinity HER2 binding affibody molecule. Cancer Res. 66, 4339\u20134348 (2006).","journal-title":"Cancer Res."},{"key":"154_CR28","doi-asserted-by":"publisher","first-page":"707","DOI":"10.1038\/nchembio.2007.31","volume":"3","author":"MW Popp","year":"2007","unstructured":"Popp, M. W., Antos, J. M., Grotenbreg, G. M., Spooner, E. & Ploegh, H. L. Sortagging: a versatile method for protein labeling. Nat. Chem. Biol. 3, 707\u2013708 (2007).","journal-title":"Nat. Chem. Biol."},{"key":"154_CR29","doi-asserted-by":"publisher","first-page":"589","DOI":"10.1016\/j.foodchem.2015.09.085","volume":"196","author":"M Russo","year":"2016","unstructured":"Russo, M. et al. Understanding genistein in cancer: the \u2018good\u2019 and the \u2018bad\u2019 effects: a review. Food Chem. 196, 589\u2013600 (2016).","journal-title":"Food Chem."},{"key":"154_CR30","doi-asserted-by":"publisher","first-page":"46","DOI":"10.1021\/ja510695g","volume":"137","author":"R Thyer","year":"2015","unstructured":"Thyer, R., Robotham, S. A., Brodbelt, J. S. & Ellington, A. D. Evolving tRNASec for efficient canonical incorporation of selenocysteine. J. Am. Chem. Soc. 137, 46\u201349 (2015).","journal-title":"J. Am. Chem. Soc."},{"key":"154_CR31","doi-asserted-by":"publisher","first-page":"12451","DOI":"10.1073\/pnas.0800800105","volume":"105","author":"T Hofer","year":"2008","unstructured":"Hofer, T., Thomas, J. D., Burke, T. R. & Rader, C. An engineered selenocysteine defines a unique class of antibody derivatives. Proc. Natl Acad. Sci. USA 105, 12451\u201312456 (2008).","journal-title":"Proc. Natl Acad. Sci. USA"},{"key":"154_CR32","doi-asserted-by":"publisher","first-page":"325","DOI":"10.1159\/000237016","volume":"107","author":"R Beasley","year":"1995","unstructured":"Beasley, R., Pearce, N., Crane, J. & Burgess, C. Withdrawal of fenoterol and the end of the New Zealand asthma mortality epidemic. Int. Arch. Allergy Immunol. 107, 325\u2013327 (1995).","journal-title":"Int. Arch. Allergy Immunol."},{"key":"154_CR33","doi-asserted-by":"publisher","first-page":"1761","DOI":"10.1517\/14656566.2014.937706","volume":"15","author":"Y Miyamoto","year":"2014","unstructured":"Miyamoto, Y., Sakamoto, Y., Yoshida, N. & Baba, H. Efficacy of S-1 in colorectal cancer. Expert. Opin. Pharmacother. 15, 1761\u20131770 (2014).","journal-title":"Expert. Opin. Pharmacother."},{"key":"154_CR34","doi-asserted-by":"publisher","first-page":"101","DOI":"10.1111\/j.1527-3458.2002.tb00218.x","volume":"8","author":"K Wi\u015bniewski","year":"2002","unstructured":"Wi\u015bniewski, K. & Car, H. (S)-3,5-DHPG: a review. CNS Drug. Rev. 8, 101\u2013116 (2002).","journal-title":"CNS Drug. Rev."},{"key":"154_CR35","doi-asserted-by":"publisher","first-page":"108","DOI":"10.1007\/BF03161019","volume":"2","author":"GM Chan","year":"2006","unstructured":"Chan, G. M., Sharma, R., Price, D., Hoffman, R. S. & Nelson, L. S. Phentolamine therapy for cocaine-associated acute coronary syndrome (CAACS). J. Med. Toxicol. 2, 108\u2013111 (2006).","journal-title":"J. Med. Toxicol."},{"key":"154_CR36","doi-asserted-by":"crossref","unstructured":"Wong, G. W. K., . & Boyda, H. N. & Wright, J. M. Blood pressure lowering efficacy of partial agonist beta blocker monotherapy for primary hypertension. Cochrane Database Syst. Rev. CD007450 (2014).","DOI":"10.1002\/14651858.CD007450.pub2"},{"key":"154_CR37","doi-asserted-by":"publisher","first-page":"1527","DOI":"10.1126\/science.274.5292.1527","volume":"274","author":"KP Lesch","year":"1996","unstructured":"Lesch, K.-P. et al. Association of anxiety-related traits with a polymorphism in the serotonin transporter gene regulatory region. Science 274, 1527\u20131531 (1996).","journal-title":"Science"}],"container-title":["Nature Chemistry"],"original-title":[],"language":"en","link":[{"URL":"http:\/\/www.nature.com\/articles\/s41557-018-0154-0","content-type":"text\/html","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/www.nature.com\/articles\/s41557-018-0154-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"text-mining"},{"URL":"http:\/\/www.nature.com\/articles\/s41557-018-0154-0.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2023,5,20]],"date-time":"2023-05-20T21:42:40Z","timestamp":1684618960000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.nature.com\/articles\/s41557-018-0154-0"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2018,11,5]]},"references-count":37,"journal-issue":{"issue":"1","published-print":{"date-parts":[[2019,1]]}},"alternative-id":["154"],"URL":"https:\/\/doi.org\/10.1038\/s41557-018-0154-0","relation":{},"ISSN":["1755-4330","1755-4349"],"issn-type":[{"value":"1755-4330","type":"print"},{"value":"1755-4349","type":"electronic"}],"subject":[],"published":{"date-parts":[[2018,11,5]]},"assertion":[{"value":"19 February 2017","order":1,"name":"received","label":"Received","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"7 September 2018","order":2,"name":"accepted","label":"Accepted","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"5 November 2018","order":3,"name":"first_online","label":"First Online","group":{"name":"ArticleHistory","label":"Article History"}},{"value":"K.D.J., Z.S. and O.P. are employees of Visterra Inc. D.T.C., C.Z., S.L.B. and B.L.P. are inventors on a patent filed by MIT-TLO to cover this work (US patent application no. 15,187,169 and international application (PCT\/US16\/38372).","order":1,"name":"Ethics","group":{"name":"EthicsHeading","label":"Competing interests"}}]}}