Cyclic peptides are polypeptide chains which contain a circular sequence of bonds.[1] This can be through a connection between the amino and carboxyl ends of the peptide, for example in cyclosporin; a connection between the amino end and a side chain, for example in bacitracin; the carboxyl end and a side chain, for example in colistin; or two side chains or more complicated arrangements, for example in alpha-amanitin. Many cyclic peptides have been discovered in nature and many others have been synthesized in the laboratory. Their length ranges from just two amino acid residues to hundreds. In nature they are frequently antimicrobial or toxic; in medicine they have various applications, for example as antibiotics and immunosuppressive agents.[2]Thin-Layer Chromatography (TLC) is a convenient method to detect cyclic peptides in crude extract from bio-mass.[3]
Cyclic peptides can be classified according to the types of bonds that comprise the ring.
Homodetic cyclic peptides, such as cyclosporine A, are those in which the ring is composed exclusively of normal peptide bonds (i.e. between the alpha carboxyl of one residue to the alpha amine of another). The smallest such species are 2,5-diketopiperazines,[4] being derived from the cyclisation of a dipeptide.
Cyclic isopeptides contain at least one non-alpha amide linkage, such as a linkage between the side chain of one residue to the alpha carboxyl group of another residue, as in microcystin and bacitracin.
Cyclic depsipeptides, such as aureobasidin A and HUN-7293, have at least one lactone (ester) linkage in place of one of the amides. Some cyclic depsipeptides are cyclized between the C-terminal carboxyl and the side chain of a Thr or Ser residue in the chain, such as kahalalide F, theonellapeptolide, and didemnin B.
Bicyclics such as the amanitins and the phalloidins contain a bridging group, generally between two of the side chains. In the amatoxins, this is formed as a sulfoxide bridge between the Trp and Cys residues. Other bicyclic peptides include echinomycin, triostin A, and Celogentin C.
There are a number of bi and monocyclic peptides which are cyclized through a disulfide bond between two cysteines, oxytocin being a notable example.
Biosynthesisedit
Cyclic peptides in plants are synthesized via a two-step process; the translation of a linear peptide chain, and its subsequent formation into a cyclic structure through activities of a protease-like enzyme or other ways.[5][6][7]
Properties and applicationsedit
Cyclic peptides tend to be extremely resistant to the process of digestion, making them of interest to scientists working on novel oral medications.[8]
^Jensen, Knud (2009-09-01). Peptide and Protein Design for Biopharmaceutical Applications. John Wiley & Sons. ISBN9780470749715.
^Wenyan, Xu; Jun, Tang; Changjiu, Ji; Wenjun, He; Ninghua, Tan (2008). "Application of a TLC chemical method to detection of cyclotides in plants". Science Bulletin. 53 (11): 1671–1674. Bibcode:2008SciBu..53.1671W. doi:10.1007/s11434-008-0178-8.
^Borthwick AD (May 2012). "2,5-Diketopiperazines: Synthesis, Reactions, Medicinal Chemistry, and Bioactive Natural Products". Chemical Reviews. 112 (7): 3641–3716. doi:10.1021/cr200398y. PMID 22575049.
^Barber, Carla J. S.; Pujara, Pareshkumar T.; Reed, Darwin W.; Chiwocha, Shiela; Zhang, Haixia; Covello, Patrick S. (2013). "The Two-step Biosynthesis of Cyclic Peptides from Linear Precursors in a Member of the Plant Family Caryophyllaceae Involves Cyclization by a Serine Protease-like Enzyme". Journal of Biological Chemistry. 288 (18): 12500–12510. doi:10.1074/jbc.M112.437947. PMC3642298. PMID 23486480.
^Wenyan Xu; et al. (2011). "Various mechanisms in cyclopeptide production from precursors synthesized independently of non-ribosomal peptide synthetases". Acta Biochimica et Biophysica Sinica. 43 (10): 757–762. doi:10.1093/abbs/gmr062. PMC3180235. PMID 21764803.
^Wenyan Xu; et al. "Plant Cyclopeptides and Possible Biosynthetic Mechanisms". {{cite journal}}: Cite journal requires |journal= (help)
^David J. Craik (17 March 2006). "Seamless Proteins Tie Up Their Loose Ends". Science. 311 (5767): 1563–7. doi:10.1126/science.1125248. PMID 16543448. S2CID 82425866.
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Cyclic peptides are polypeptide chains which contain a circular sequence of bonds 1 This can be through a connection between the amino and carboxyl ends of the peptide for example in cyclosporin a connection between the amino end and a side chain for example in bacitracin the carboxyl end and a side chain for example in colistin or two side chains or more complicated arrangements for example in alpha amanitin Many cyclic peptides have been discovered in nature and many others have been synthesized in the laboratory Their length ranges from just two amino acid residues to hundreds In nature they are frequently antimicrobial or toxic in medicine they have various applications for example as antibiotics and immunosuppressive agents 2 Thin Layer Chromatography TLC is a convenient method to detect cyclic peptides in crude extract from bio mass 3 a AmanitinBacitracinCiclosporin Contents 1 Classification 2 Biosynthesis 3 Properties and applications 4 See also 5 References 6 External linksClassification editCyclic peptides can be classified according to the types of bonds that comprise the ring Homodetic cyclic peptides such as cyclosporine A are those in which the ring is composed exclusively of normal peptide bonds i e between the alpha carboxyl of one residue to the alpha amine of another The smallest such species are 2 5 diketopiperazines 4 being derived from the cyclisation of a dipeptide Cyclic isopeptides contain at least one non alpha amide linkage such as a linkage between the side chain of one residue to the alpha carboxyl group of another residue as in microcystin and bacitracin Cyclic depsipeptides such as aureobasidin A and HUN 7293 have at least one lactone ester linkage in place of one of the amides Some cyclic depsipeptides are cyclized between the C terminal carboxyl and the side chain of a Thr or Ser residue in the chain such as kahalalide F theonellapeptolide and didemnin B Bicyclics such as the amanitins and the phalloidins contain a bridging group generally between two of the side chains In the amatoxins this is formed as a sulfoxide bridge between the Trp and Cys residues Other bicyclic peptides include echinomycin triostin A and Celogentin C There are a number of bi and monocyclic peptides which are cyclized through a disulfide bond between two cysteines oxytocin being a notable example Biosynthesis editCyclic peptides in plants are synthesized via a two step process the translation of a linear peptide chain and its subsequent formation into a cyclic structure through activities of a protease like enzyme or other ways 5 6 7 Properties and applications editCyclic peptides tend to be extremely resistant to the process of digestion making them of interest to scientists working on novel oral medications 8 Examples include Amanitins Bacitracin Colistin Ciclosporin Dactinomycin Daptomycin Gramicidin S Hymenistatin Microcystins Nisin Nodularin Octreotide Polymyxin B Pristinamycin Valinomycin technically a depsipeptide Vancomycin Viscumamide Yunnanin ASee also editNonribosomal peptide lantibiotics 19 37 residues and 1 to 5 bridges References edit Salehi David Mozaffari Saghar Zoghebi Khalid Lohan Sandeep Mandal Dindyal Tiwari Rakesh K Parang Keykavous 2022 03 29 Amphiphilic Cell Penetrating Peptides Containing Natural and Unnatural Amino Acids as Drug Delivery Agents Cells 11 7 1156 doi 10 3390 cells11071156 ISSN 2073 4409 PMC 8997995 PMID 35406720 Jensen Knud 2009 09 01 Peptide and Protein Design for Biopharmaceutical Applications John Wiley amp Sons ISBN 9780470749715 Wenyan Xu Jun Tang Changjiu Ji Wenjun He Ninghua Tan 2008 Application of a TLC chemical method to detection of cyclotides in plants Science Bulletin 53 11 1671 1674 Bibcode 2008SciBu 53 1671W doi 10 1007 s11434 008 0178 8 Borthwick AD May 2012 2 5 Diketopiperazines Synthesis Reactions Medicinal Chemistry and Bioactive Natural Products Chemical Reviews 112 7 3641 3716 doi 10 1021 cr200398y PMID 22575049 Barber Carla J S Pujara Pareshkumar T Reed Darwin W Chiwocha Shiela Zhang Haixia Covello Patrick S 2013 The Two step Biosynthesis of Cyclic Peptides from Linear Precursors in a Member of the Plant Family Caryophyllaceae Involves Cyclization by a Serine Protease like Enzyme Journal of Biological Chemistry 288 18 12500 12510 doi 10 1074 jbc M112 437947 PMC 3642298 PMID 23486480 Wenyan Xu et al 2011 Various mechanisms in cyclopeptide production from precursors synthesized independently of non ribosomal peptide synthetases Acta Biochimica et Biophysica Sinica 43 10 757 762 doi 10 1093 abbs gmr062 PMC 3180235 PMID 21764803 Wenyan Xu et al Plant Cyclopeptides and Possible Biosynthetic Mechanisms a href Template Cite journal html title Template Cite journal cite journal a Cite journal requires journal help David J Craik 17 March 2006 Seamless Proteins Tie Up Their Loose Ends Science 311 5767 1563 7 doi 10 1126 science 1125248 PMID 16543448 S2CID 82425866 External links editCybase Cyclic Peptides at the U S National Library of Medicine Medical Subject Headings MeSH Retrieved from https en wikipedia org w index php title Cyclic peptide amp oldid 1182890151, wikipedia, wiki, book, books, library,
