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Download Author Version (PDF) Chemical Society Reviews Developments and recent advancements in the field of endogenous amino acid selective bond forming reactions for bioconjugation Journal: Chemical Society Reviews Manuscript ID: CS-SYN-01-2015-000048.R2 Article Type: Review Article Date Submitted by the Author: 07-Apr-2015 Complete List of Authors: Koniev, Oleksandr; University of Strasbourg, LFCS, UMR7199 Wagner, Alain; University of Strasbourg, LFCS, UMR7199 Page 1 of 73 Chemical Society Reviews Developments and recent advancements in the field of en- dogenous amino acid selective bond forming reactions for bioconjugation Oleksandr Koniev †§ and Alain Wagner †* †Laboratory of Functional Chemo-Systems (UMR 7199), Labex Medalis, University of Strasbourg, 74 Route du Rhin, 67401 Illkirch-Graffenstaden, France §Syndivia SAS, 4 rue Boussingault, 67000 Strasbourg, France Chemical Society Reviews Page 2 of 73 2 Page 3 of 73 Chemical Society Reviews Bioconjugation methodologies have proven to play a central enabling role in the recent development of biotherapeutics and chemical biology approaches. Recent en- deavours in these fields shed light on unprecedented chemical challenges to attain the bioselectivity, the biocompatibility, and the biostability required by modern applica- tions. In this review the current developments in various techniques of selective bond forming reactions on proteins and peptides were highlighted. The utility of each en- dogenous amino acid-selective conjugation methodology in the area of biologics and protein science has been surveyed with emphasis on most relevant among reported transformations; selectivity and practical use have been discussed. 3 Chemical Society Reviews Page 4 of 73 Contents Introduction ................................................................................................................................................... 5 1. In-chain conjugation ........................................................................................................................... 5 1.1 Lysine ............................................................................................................................................................. 5 1.1.1 Isocyanates and Isothiocyanates ..................................................................................................................... 6 1.1.2 Activated esters ...................................................................................................................................................... 8 1.1.3 Reductive Amination of Aldehydes ............................................................................................................. 10 1.1.4 Sulfonyl Halides and Sulfonates .................................................................................................................... 11 1.1.5 Fluorobenzenes ................................................................................................................................................... 12 1.1.6 Imidoesters ............................................................................................................................................................ 13 1.1.7 Miscellaneous amine-selective reagents ................................................................................................... 13 1.2 Serine and Threonine ............................................................................................................................ 14 1.3 Cysteine ....................................................................................................................................................... 15 1.3.1 α-Halocarbonyls .................................................................................................................................................. 15 1.3.2 Maleimides ............................................................................................................................................................ 16 1.3.3 Vinyl sulfones ....................................................................................................................................................... 18 1.3.4 Thiol-ene coupling .............................................................................................................................................. 19 1.3.5 Thiol–yne coupling ............................................................................................................................................. 19 1.3.6 Disulfide reaction ................................................................................................................................................ 20 Disulfide rebridging .......................................................................................................................................... 21 1.3.8 Transforming to dehydroalanine ................................................................................................................. 23 1.3.9 Miscellaneous thiol-selective reagents ...................................................................................................... 25 1.4 Tryptophan ................................................................................................................................................ 26 1.4.1 Malondialdehydes .............................................................................................................................................. 26 1.4.2 Metallocarbenoids .............................................................................................................................................. 27 1.5 Histidine ..................................................................................................................................................... 28 1.5.1 Epoxides ................................................................................................................................................................. 29 1.5.2 Complexes with transition metals ............................................................................................................... 30 1.5.3 Michael addition .................................................................................................................................................. 30 1.5.4 Miscellaneous histidine-selective reagents ............................................................................................. 31 1.6 Tyrosine ...................................................................................................................................................... 31 1.6.1 O-Derivatisation .................................................................................................................................................. 31 1.6.2 O-Oxidatiove coupling ....................................................................................................................................... 34 1.6.3 Diazonium reagents ........................................................................................................................................... 35 1.6.4 Mannich-type reaction ...................................................................................................................................... 35 1.6.5 Dicarboxylates and dicarboxamides ........................................................................................................... 36 1.7 Arginine ...................................................................................................................................................... 37 1.8 Aspartic and glutamic acids ................................................................................................................. 38 1.9 Methionine ................................................................................................................................................. 39 2 N-terminal conjugation ..................................................................................................................... 40 2.1 α-Amino groups ....................................................................................................................................... 40 2.1.1 Classical approaches .......................................................................................................................................... 40 2.1.2 Ketene-mediated conjugation ....................................................................................................................... 40 2.1.3 Transamination ................................................................................................................................................... 40 2.1.4 2-Pyridinecarboxyaldehydes (2PCA) ......................................................................................................... 42 2.2 Serine and Threonine ............................................................................................................................ 43 2.2.1 O → N shift of oxazolidines ............................................................................................................................. 43 2.2.2 Periodate oxidation ............................................................................................................................................ 43 2.2.3 Phosphate-assisted ligation ............................................................................................................................ 44 2.2.4 Indirect approaches ..........................................................................................................................................
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