Abstract
O.B. thanks the European Commission (Marie Curie CIG) and Ministerio de Ciencia e Innovacion, Spain (Juan de la Cierva Fellowship). G.J.L.B. thanks his generous sources of funding: Royal Society, FCT Portugal (FCT Investigator), European Commission (Marie Curie CIG), and the EPSRC. G.J.L.B. is a Royal Society University Research Fellow. The authors thank Paula Boutureira Regla and Francisco Pinteus da Cruz Lopes Bernardes for inspiration.
Highlights
Alternativeenzymatic strategies use two-step procedures involving, first, a chemical oxidation with (i) sodium periodate,[99] (ii) a site-selective transamination reaction[100] with pyridoxal 5′-phosphate or related reagents (Rapoport’s salt), or (iii) an enzymatic tagging with formylglycine-generating enzymes (FGEs)[101] to efficiently install an aldehyde handle that can be modified with a second, carbonyl-selective reaction.[102]
Relevant examples include the well-known oxime (Scheme 11a)[103] and hydrazide (Scheme 11b)[104] ligations together with a related reaction with 2-amino benzamidoxime (ABAO) derivatives (Scheme 11c),[105] the Pictet−Spengler ligation (Scheme 11e),[106] which is more rapid than its parent version (Scheme 11d), and, more recently, the so-called hydrazinoPictet−Spengler (HIPS) ligation (Scheme 11e).[107]
This review has highlighted the state of the art of recent aqueous reaction methodology developed for site-selective chemical protein modification
Summary
Maleimide Michael Acceptor nous amino acids[7] to more specialized topics such as click modification protocols,[8] the introduction of particular PTMs including glycosylation,[9] PEGylation,5b,10 and polymerization of protein-based initiators,[11] and the challenging labeling of a specific protein of interest in a complex cellular mixture using the so-called “bioorthogonal” reactions,[12] have been published during the past decade. While the later publications describe different protein syntheses/modifications in detail, the aim of the present review is not to be an exhaustive survey of all available bioconjugation methodologies but to discuss recent chemical strategies for the site-selective modification of proteins such as fast sulfur exchange or stable thioether formation, photo and metal-free cycloadditions, and other challenging metalmediated protocols.
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