Bioconjugation with Strained Alkenes and Alkynes - Accounts of Chemical Research (ACS Publications) pandora siopa

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Bioconjugation with Strained Alkenes and Alkynes

Marjoke F. Debets , Sander S. van Berkel , Jan Dommerholt , A. (Ton) J. Dirks , Floris P. J. T. Rutjes , and Floris L. van Delft * Institute for Molecules and Materials, Radboud University Nijmegen , Heyendaalseweg 135, 6525 AJ, The Netherlands Acc. Chem. Res. , 2011 , 44 (9), pp 805–815DOI: 10.1021/ar200059zPublication Date (Web): July 18, 2011Copyright © 2011 American Chemical SocietyTo whom correspondence should be addressed. E-mail: F.vanDelft@science.ru.nl.This article is part of the Bioorthogonal Chemistry in Biology special issue. Biography

Marjoke F. Debets is a Ph.D. student at the Radboud University Nijmegen, working under the guidance of Prof. Rutjes and Prof. van Hest, with focus on the development and application of new bioorthogonal ligations. Before that, she completed her M.Sc. in chemistry at the same university (2008) and performed a research internship in the group of Prof. Erik Sorensen (Princeton University, Princeton, NJ).

Biography

Sander S. van Berkel obtained his Ph.D. in chemistry at the Radboud University Nijmegen in 2008 under the supervision of Prof. Rutjes. His research involved various topics including metal-free cycloaddition reactions. He then moved to the Leibniz Institute of Plant Biochemistry for a postdoctoral stay, where he worked on the synthesis of novel antimitotics under the supervision of Prof. Wessjohann. At present, he is a postdoctoral fellow at the Radboud University Nijmegen in the research group of Prof. van Hest, conducting research on surface modifications with bioorthogonal reactions.

Biography

Jan Dommerholt is a technician at the Radboud University Nijmegen since 1985. He is the recipient of the Trooster prize 2010.

Biography

Ton Dirks received his Ph.D. degree (2009) from the Radboud University Nijmegen, where he studied (amphiphilic) protein–polymer conjugates in the groups of Prof. Nolte and Prof. Cornelissen. Currently, he is working as a scientist in biomedical materials at DSM, Geleen.

Biography

Floris P. J. T. Rutjes is full professor in synthetic organic chemistry with research focus on application of catalysis (bio- and transition metal catalysis), on synthesis of biologically relevant molecules, on development of diagnostic tools, and on synthesis in microreactors. He obtained his Ph.D. at the University of Amsterdam (1993), under the supervision of Prof. Speckamp, before conducting postdoctoral research in the group of Prof. Nicolaou (The Scripps Research Institute, La Jolla, CA). In 1995, he was appointed assistant professor at the University of Amsterdam and became full professor at Radboud University Nijmegen in 1999.

Biography

Floris L. van Delft is an associate professor with special interest in the synthesis of glycoproteins (isosteres) and bioorthogonal chemistry. He received his Ph.D. at the University of Leiden (1996, cum laude) under the supervision of the late Prof. van Boom and conducted postdoctoral research in the group of Prof. Nicolaou (The Scripps Research Institute, La Jolla, CA). In 1998, he became assistant professor in bioorganic chemistry at the University of Amsterdam before moving to Radboud University Nijmegen (1999).

Abstract

Abstract Image

The structural complexity of molecules isolated from biological sources has always served as an inspiration for organic chemists. Since the first synthesis of a natural product, urea, chemists have been challenged to prepare exact copies of natural structures in the laboratory. As a result, a broad repertoire of synthetic transformations has been developed over the years. It is now feasible to synthesize organic molecules of enormous complexity, and also molecules with less structural complexity but prodigious societal impact, such as nylon, TNT, polystyrene, statins, estradiol, XTC, and many more.

Unfortunately, only a few chemical transformations are so mild and precise that they can be used to selectively modify biochemical structures, such as proteins or nucleic acids; these are the so-called bioconjugation strategies. Even more challenging is to apply a chemical reaction on or in living cells or whole organisms; these are the so-called bioorthogonal reactions. These fields of research are of particular importance because they not only pose a worthy challenge for chemists but also offer unprecedented possibilities for studying biological systems, especially in areas in which traditional biochemistry and molecular biology tools fall short.

Recent years have seen tremendous growth in the chemical biology toolbox. In particular, a rapidly increasing number of bioorthogonal reactions has been developed based on chemistry involving strained alkenes or strained alkynes. Such strained unsaturated systems have the unique ability to undergo (3 + 2) and (4 + 2) cycloadditions with a diverse set of complementary reaction partners. Accordingly, chemistry centered around strain-promoted cycloadditions has been exploited to precisely modify biopolymers, ranging from nucleic acids to proteins to glycans.

In this Account, we describe progress in bioconjugation centered around cycloadditions of these strained unsaturated systems. Being among the first to recognize the utility of strain-promoted cycloadditions between alkenes and dipoles, we highlight our report in 2007 of the reaction of oxanobornadienes with azides, which occurs through a sequential cycloaddition and retro Diels–Alder reaction. We further consider the subsequent refinement of this reaction as a valuable tool in chemical biology. We also examine the development of the reaction of cyclooctyne, the smallest isolable cyclic alkyne, with a range of substrates. Owing to severe deformation of the triple bond from ideal linear geometry, the cyclooctynes show high reactivity toward dienes, 1,3-dipoles, and other molecular systems. In the search for bioorthogonal reactions, cycloadditions of cyclic alkenes and alkynes have now established themselves as powerful tools in reagent-free bioconjugations.

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