Enzymatic Macrocyclization of 1,2,3-Triazole Peptide Mimetics
The macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are available for their chemical macrocyclization, however, enzyme‐mediated methods remain of great interest in terms of synthetic utility. To dat...
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Published in | Angewandte Chemie International Edition Vol. 55; no. 19; pp. 5842 - 5845 |
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Main Authors | , , , |
Format | Journal Article |
Language | English |
Published |
WEINHEIM
Blackwell Publishing Ltd
04.05.2016
Wiley Wiley Subscription Services, Inc John Wiley and Sons Inc |
Edition | International ed. in English |
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Abstract | The macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are available for their chemical macrocyclization, however, enzyme‐mediated methods remain of great interest in terms of synthetic utility. To date, known macrocyclization enzymes have been shown to be active on both peptide and protein substrates. Here we show that the macrocyclization enzyme of the cyanobactin family, PatGmac, is capable of macrocyclizing substrates with one, two, or three 1,4‐substituted 1,2,3‐triazole moieties. The introduction of non‐peptidic scaffolds into macrocycles is highly desirable in tuning the activity and physical properties of peptidic macrocycles. We have isolated and fully characterized nine non‐natural triazole‐containing cyclic peptides, a further ten molecules are also synthesized. PatGmac has now been shown to be an effective and versatile tool for the ring closure by peptide bond formation.
The macrocyclase enzyme PatGmac from the patellamide pathway of the cyanobactin family successfully macrocyclized non‐natural peptides where one, two, or three 1,4‐substituted 1,2,3‐triazole rings were incorporated at different positions of the core peptide. 19 cyclic peptides were macrocyclized by PatGmac, among which 9 were isolated and fully characterized. |
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AbstractList | The macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are available for their chemical macrocyclization, however, enzyme-mediated methods remain of great interest in terms of synthetic utility. To date, known macrocyclization enzymes have been shown to be active on both peptide and protein substrates. Here we show that the macrocyclization enzyme of the cyanobactin family, PatGmac, is capable of macrocyclizing substrates with one, two, or three 1,4-substituted 1,2,3-triazole moieties. The introduction of non-peptidic scaffolds into macrocycles is highly desirable in tuning the activity and physical properties of peptidic macrocycles. We have isolated and fully characterized nine non-natural triazole-containing cyclic peptides, a further ten molecules are also synthesized. PatGmac has now been shown to be an effective and versatile tool for the ring closure by peptide bond formation. The macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are available for their chemical macrocyclization, however, enzyme‐mediated methods remain of great interest in terms of synthetic utility. To date, known macrocyclization enzymes have been shown to be active on both peptide and protein substrates. Here we show that the macrocyclization enzyme of the cyanobactin family, PatGmac, is capable of macrocyclizing substrates with one, two, or three 1,4‐substituted 1,2,3‐triazole moieties. The introduction of non‐peptidic scaffolds into macrocycles is highly desirable in tuning the activity and physical properties of peptidic macrocycles. We have isolated and fully characterized nine non‐natural triazole‐containing cyclic peptides, a further ten molecules are also synthesized. PatGmac has now been shown to be an effective and versatile tool for the ring closure by peptide bond formation. The macrocyclase enzyme PatGmac from the patellamide pathway of the cyanobactin family successfully macrocyclized non‐natural peptides where one, two, or three 1,4‐substituted 1,2,3‐triazole rings were incorporated at different positions of the core peptide. 19 cyclic peptides were macrocyclized by PatGmac, among which 9 were isolated and fully characterized. |
Author | Oueis, Emilia Westwood, Nicholas J. Jaspars, Marcel Naismith, James H. |
AuthorAffiliation | 1 Biomedical Science Research Complex University of St Andrews, BSRC North Haugh St Andrews KY16 9ST UK 3 Marine Biodiscovery Centre, Department of Chemistry University of Aberdeen Old Aberdeen AB24 3UE UK 2 State Key Laboratory of Biotherapy Sichuan University China |
AuthorAffiliation_xml | – name: 1 Biomedical Science Research Complex University of St Andrews, BSRC North Haugh St Andrews KY16 9ST UK – name: 2 State Key Laboratory of Biotherapy Sichuan University China – name: 3 Marine Biodiscovery Centre, Department of Chemistry University of Aberdeen Old Aberdeen AB24 3UE UK |
Author_xml | – sequence: 1 givenname: Emilia surname: Oueis fullname: Oueis, Emilia organization: Biomedical Science Research Complex, University of St Andrews, BSRC, North Haugh, KY16 9ST, St Andrews, UK – sequence: 2 givenname: Marcel surname: Jaspars fullname: Jaspars, Marcel organization: Marine Biodiscovery Centre, Department of Chemistry, University of Aberdeen, AB24 3UE, Old Aberdeen, UK – sequence: 3 givenname: Nicholas J. surname: Westwood fullname: Westwood, Nicholas J. organization: Biomedical Science Research Complex, University of St Andrews, BSRC, North Haugh, KY16 9ST, St Andrews, UK – sequence: 4 givenname: James H. surname: Naismith fullname: Naismith, James H. email: naismith@st-andrews.ac.uk organization: Biomedical Science Research Complex, University of St Andrews, BSRC, KY16 9ST, St Andrews, North Haugh, UK |
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Keywords | cyclic peptides biotransformation DRUG DISCOVERY CHEMISTRY cyanobactin peptidomimetics CYCLIZATION triazole |
Language | English |
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Snippet | The macrocyclization of linear peptides is very often accompanied by significant improvements in their stability and biological activity. Many strategies are... |
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SubjectTerms | Amino Acid Sequence biotransformation Chemistry Chemistry, Multidisciplinary Communication Communications cyanobactin cyclic peptides Cyclization Enzymes Peptide Hydrolases - metabolism Peptides Peptides, Cyclic - chemistry Peptides, Cyclic - metabolism peptidomimetics Physical Sciences Science & Technology Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization triazole Triazoles - chemistry |
Title | Enzymatic Macrocyclization of 1,2,3-Triazole Peptide Mimetics |
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