Orthogonality in organic, polymer, and supramolecular chemistry: from Merrifield to click chemistry
The concept of orthogonality has been applied to many areas of chemistry, ranging from wave functions to chromatography. But it was Barany and Merrifield's orthogonal protecting group strategy that paved the way for solid phase peptide syntheses, other important classes of biomaterials such as...
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| Published in | Chemical communications (Cambridge, England) Vol. 49; no. 17; pp. 1679 - 1695 |
|---|---|
| Main Authors | , |
| Format | Journal Article |
| Language | English |
| Published |
England
01.01.2013
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| Subjects | |
| Online Access | Get full text |
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| Abstract | The concept of orthogonality has been applied to many areas of chemistry, ranging from wave functions to chromatography. But it was Barany and Merrifield's orthogonal protecting group strategy that paved the way for solid phase peptide syntheses, other important classes of biomaterials such as oligosaccharides and oligonucleotides, and ultimately to a term in widespread usage that is focused on chemical reactivity and binding selectivity. The orthogonal protection strategy has been extended to the development of orthogonal activation, and recently the click reaction, for streamlining organic synthesis. The click reaction and its variants are considered orthogonal as the components react together in high yield and in the presence of many other functional groups. Likewise, supramolecular building blocks can also be orthogonal, thereby enabling programmed self-assembly, a superb strategy to create complex architectures. Overall, orthogonal reactions and supramolecular interactions have dramatically improved the syntheses, the preparation of functional materials, and the self-assembly of nanoscale structures.
This Feature Article traces the history of orthogonality in synthetic chemistry from Merrifield up through supramolecular chemistry and into click and bioorthogonal click processes. |
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| AbstractList | The concept of orthogonality has been applied to many areas of chemistry, ranging from wave functions to chromatography. But it was Barany and Merrifield's orthogonal protecting group strategy that paved the way for solid phase peptide syntheses, other important classes of biomaterials such as oligosaccharides and oligonucleotides, and ultimately to a term in widespread usage that is focused on chemical reactivity and binding selectivity. The orthogonal protection strategy has been extended to the development of orthogonal activation, and recently the click reaction, for streamlining organic synthesis. The click reaction and its variants are considered orthogonal as the components react together in high yield and in the presence of many other functional groups. Likewise, supramolecular building blocks can also be orthogonal, thereby enabling programmed self-assembly, a superb strategy to create complex architectures. Overall, orthogonal reactions and supramolecular interactions have dramatically improved the syntheses, the preparation of functional materials, and the self-assembly of nanoscale structures. The concept of orthogonality has been applied to many areas of chemistry, ranging from wave functions to chromatography. But it was Barany and Merrifield's orthogonal protecting group strategy that paved the way for solid phase peptide syntheses, other important classes of biomaterials such as oligosaccharides and oligonucleotides, and ultimately to a term in widespread usage that is focused on chemical reactivity and binding selectivity. The orthogonal protection strategy has been extended to the development of orthogonal activation, and recently the click reaction, for streamlining organic synthesis. The click reaction and its variants are considered orthogonal as the components react together in high yield and in the presence of many other functional groups. Likewise, supramolecular building blocks can also be orthogonal, thereby enabling programmed self-assembly, a superb strategy to create complex architectures. Overall, orthogonal reactions and supramolecular interactions have dramatically improved the syntheses, the preparation of functional materials, and the self-assembly of nanoscale structures. This Feature Article traces the history of orthogonality in synthetic chemistry from Merrifield up through supramolecular chemistry and into click and bioorthogonal click processes. |
| Author | Wong, Chun-Ho Zimmerman, Steven C |
| AuthorAffiliation | Department of Chemistry University of Illinois at Urbana-Champaign |
| AuthorAffiliation_xml | – name: University of Illinois at Urbana-Champaign – name: Department of Chemistry |
| Author_xml | – sequence: 1 givenname: Chun-Ho surname: Wong fullname: Wong, Chun-Ho – sequence: 2 givenname: Steven C surname: Zimmerman fullname: Zimmerman, Steven C |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/23282586$$D View this record in MEDLINE/PubMed |
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| Notes | Steven C. Zimmerman was born in Evanston, Illinois, in 1957. He received his BS from the University of Wisconsin, his PhD from Columbia University, and was an NSF-NATO Postdoctoral Fellow at Cambridge University. He joined the University of Illinois faculty in 1985, served as interim or permanent Head of the Department for eight years, and is currently the Roger Adams Professor of Chemistry. He has broad interests in organic, polymer, and supramolecular chemistry and their interface with biology and materials chemistry. He dedicates this article to his father-in-law, Prof. Isaiah Shavitt (1925-2012) and his father, Prof. Howard E. Zimmerman (1926-2012). Chun-Ho Wong was born in Hong Kong in 1982. He received his first-class BSc (Hons) in Chemistry in 2004 and MPhil in 2006 from the Chinese University of Hong Kong, working with Prof. Hak-Fun Chow on dendrimer and supramolecular chemistry. He then spent a year as an editorial assistant at the SYNLETT (HK) regional editorial office. In 2007, he received the Croucher Foundation Scholarship and commenced his PhD research at the University of Illinois at Urbana-Champaign under the guidance of Prof. Steven C. Zimmerman working on drug discovery for myotonic dystrophy. His research interests include drug design and chemical biology. ObjectType-Article-1 SourceType-Scholarly Journals-1 ObjectType-Feature-2 content type line 23 ObjectType-Article-2 ObjectType-Feature-1 |
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| PublicationCentury | 2000 |
| PublicationDate | 2013-01-01 |
| PublicationDateYYYYMMDD | 2013-01-01 |
| PublicationDate_xml | – month: 01 year: 2013 text: 2013-01-01 day: 01 |
| PublicationDecade | 2010 |
| PublicationPlace | England |
| PublicationPlace_xml | – name: England |
| PublicationTitle | Chemical communications (Cambridge, England) |
| PublicationTitleAlternate | Chem Commun (Camb) |
| PublicationYear | 2013 |
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| Title | Orthogonality in organic, polymer, and supramolecular chemistry: from Merrifield to click chemistry |
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