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Article: Ligation Technologies for the Synthesis of Cyclic Peptides

TitleLigation Technologies for the Synthesis of Cyclic Peptides
Authors
KeywordsPeptides and proteins
Precursors
Monomers
Cyclization
Ligation
Issue Date2019
PublisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/cr
Citation
Chemical Reviews, 2019, v. 119 n. 17, p. 9971-10001 How to Cite?
AbstractCyclic peptides have been attracting a lot of attention in recent decades, especially in the area of drug discovery, as more and more naturally occurring cyclic peptides with diverse biological activities have been discovered. Chemical synthesis of cyclic peptides is essential when studying their structure–activity relationships. Conventional peptide cyclization methods via direct coupling have inherent limitations, like the susceptibility to epimerization at the C-terminus, poor solubility of fully protected peptide precursors, and low yield caused by oligomerization. In this regard, chemoselective ligation-mediated cyclization methods have emerged as effective strategies for cyclic peptide synthesis. The toolbox for cyclic peptide synthesis has been expanded substantially in the past two decades, allowing more efficient synthesis of cyclic peptides with various scaffolds and modifications. This Review will explore different chemoselective ligation technologies used for cyclic peptide synthesis that generate both native and unnatural peptide linkages. The practical issues and limitations of different methods will be discussed. The advance in cyclic peptide synthesis will benefit the biological and medicinal study of cyclic peptides, an important class of macrocycles with potentials in numerous fields, notably in therapeutics.
Persistent Identifierhttp://hdl.handle.net/10722/284529
ISSN
2019 Impact Factor: 52.758
2015 SCImago Journal Rankings: 19.143
ISI Accession Number ID

 

DC FieldValueLanguage
dc.contributor.authorCHOW, HY-
dc.contributor.authorZHANG, Y-
dc.contributor.authorMatheson, E-
dc.contributor.authorLi, X-
dc.date.accessioned2020-08-07T08:58:57Z-
dc.date.available2020-08-07T08:58:57Z-
dc.date.issued2019-
dc.identifier.citationChemical Reviews, 2019, v. 119 n. 17, p. 9971-10001-
dc.identifier.issn0009-2665-
dc.identifier.urihttp://hdl.handle.net/10722/284529-
dc.description.abstractCyclic peptides have been attracting a lot of attention in recent decades, especially in the area of drug discovery, as more and more naturally occurring cyclic peptides with diverse biological activities have been discovered. Chemical synthesis of cyclic peptides is essential when studying their structure–activity relationships. Conventional peptide cyclization methods via direct coupling have inherent limitations, like the susceptibility to epimerization at the C-terminus, poor solubility of fully protected peptide precursors, and low yield caused by oligomerization. In this regard, chemoselective ligation-mediated cyclization methods have emerged as effective strategies for cyclic peptide synthesis. The toolbox for cyclic peptide synthesis has been expanded substantially in the past two decades, allowing more efficient synthesis of cyclic peptides with various scaffolds and modifications. This Review will explore different chemoselective ligation technologies used for cyclic peptide synthesis that generate both native and unnatural peptide linkages. The practical issues and limitations of different methods will be discussed. The advance in cyclic peptide synthesis will benefit the biological and medicinal study of cyclic peptides, an important class of macrocycles with potentials in numerous fields, notably in therapeutics.-
dc.languageeng-
dc.publisherAmerican Chemical Society. The Journal's web site is located at http://pubs.acs.org/cr-
dc.relation.ispartofChemical Reviews-
dc.rightsThis document is the Accepted Manuscript version of a Published Work that appeared in final form in [JournalTitle], copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see [insert ACS Articles on Request author-directed link to Published Work, see http://pubs.acs.org/page/policy/articlesonrequest/index.html].-
dc.subjectPeptides and proteins-
dc.subjectPrecursors-
dc.subjectMonomers-
dc.subjectCyclization-
dc.subjectLigation-
dc.titleLigation Technologies for the Synthesis of Cyclic Peptides-
dc.typeArticle-
dc.identifier.emailLi, X: xuechenl@hku.hk-
dc.identifier.authorityLi, X=rp00742-
dc.description.naturelink_to_subscribed_fulltext-
dc.identifier.doi10.1021/acs.chemrev.8b00657-
dc.identifier.pmid31318534-
dc.identifier.scopuseid_2-s2.0-85072059184-
dc.identifier.hkuros311890-
dc.identifier.volume119-
dc.identifier.issue17-
dc.identifier.spage9971-
dc.identifier.epage10001-
dc.identifier.isiWOS:000486360600008-
dc.publisher.placeUnited States-
dc.identifier.issnl0009-2665-

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