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However, the dynamic nature of these bonds also limits the control over the stability and site\u2010selectivity of the bioconjugation, which ultimately leads to heterogeneous conjugates with poor stability under physiological conditions. Here we disclose a new strategy to install BAs on peptide chains. In this study, a \u201cboron hot spot\u201c based on the 3\u2010hydroxyquinolin\u20102(1<jats:italic>H<\/jats:italic>)\u2010one scaffold was developed and upon installation on a peptide N\u2010terminal cysteine, enables the site\u2010selective formation of iminoboronates with 2\u2010formyl\u2010phenyl boronic acids (<jats:italic>K<jats:sub>a<\/jats:sub><\/jats:italic> of 58128\u00b12\u2009<jats:sc>m<\/jats:sc><jats:sup>\u22121<\/jats:sup>). The reaction is selective in the presence of competing lysine <jats:italic>\u03f5<\/jats:italic>\u2010amino groups, and the resulting iminoboronates, displayed improved stability in buffers solutions and a cleavable profile in the presence of glutathione. Once developed, the methodology was used to prepare cleavable fluorescent conjugates with a laminin fragment, which enabled the validation of the 67LR receptor as a target to deliver cargo to cancer HT29 cells.<\/jats:p>","DOI":"10.1002\/chem.202002675","type":"journal-article","created":{"date-parts":[[2020,7,6]],"date-time":"2020-07-06T05:13:00Z","timestamp":1594012380000},"page":"15226-15231","update-policy":"https:\/\/doi.org\/10.1002\/crossmark_policy","source":"Crossref","is-referenced-by-count":12,"title":["Engineering Boron Hot Spots for the Site\u2010Selective Installation of Iminoboronates on Peptide Chains"],"prefix":"10.1002","volume":"26","author":[{"given":"Roberto","family":"Russo","sequence":"first","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"}]},{"given":"Rita","family":"Padanha","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy Universidade de Lisboa  Av. Prof. Gama Pinto 1649-003 Lisboa Portugal"}]},{"given":"F\u00e1bio","family":"Fernandes","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica-F\u00edsica Molecular and Institute of Nanoscience and Nanotechnology IBB-Institute for Bioengineering and Biosciences Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1 1049-001 Lisbon Portugal"},{"name":"Centro de Qu\u00edmica Estrutural Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1 1049-001 Lisbon Portugal"}]},{"given":"Luis F.","family":"Veiros","sequence":"additional","affiliation":[{"name":"Centro de Qu\u00edmica Estrutural Instituto Superior T\u00e9cnico Universidade de Lisboa  Av. Rovisco Pais 1 1049-001 Lisbon Portugal"}]},{"given":"Francisco","family":"Corzana","sequence":"additional","affiliation":[{"name":"Departamento de Qu\u00edmica Universidad de La Rioja, Centro de Investigaci\u00f3n en S\u00edntesis Qu\u00edmica  26006 Logro\u00f1o Spain"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7698-630X","authenticated-orcid":false,"given":"Pedro M. P.","family":"Gois","sequence":"additional","affiliation":[{"name":"Research Institute for Medicines (iMed.ULisboa) Faculty of Pharmacy Universidade de Lisboa  Av. 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