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The cyclotide fingerprint in oldenlandia affinis: elucidation of chemically modified, linear and novel macrocyclic peptides.
- Source :
-
Chembiochem : a European journal of chemical biology [Chembiochem] 2007 Jun 18; Vol. 8 (9), pp. 1001-11. - Publication Year :
- 2007
-
Abstract
- The complete suite of cyclotides present in Oldenlandia affinis (Rubiaceae), the plant that was originally found to contain this unique family of circular proteins, has been characterised. This study expands the number of known cyclotides in this plant to 17, of which nine new sequences (kalata B9-B17) were characterised in this work. In addition, five derivatives that contain oxidation products of the conserved tryptophan were identified, and it was shown that the formation of these derivatives is catalysed by exposure to sunlight. Furthermore, we describe two "linear" cyclotide analogues. These acyclic peptides have three intact disulfide bonds, and their N and C termini coincide with the hypothesised cleavage sites from the precursor protein. This work increases our knowledge about the sequence variation that is accommodated by the cyclic cystine knot scaffold, confirms its applicability as a template for drug design, and also shows the first natural degradation pathways for cyclotides. These pathways have important implications for the persistence and environmental fate of the cyclotides if used as crop-protection agents.
- Subjects :
- Acetylation
Alkylation
Amino Acid Sequence
Amino Acids analysis
Chromatography, High Pressure Liquid
Cyclotides biosynthesis
Disulfides chemistry
Hemolysis drug effects
Lysine chemistry
Mass Spectrometry
Molecular Sequence Data
Molecular Weight
Oxidation-Reduction
Peptide Mapping
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Ultraviolet
Tryptophan chemistry
Cyclotides chemistry
Macrocyclic Compounds chemistry
Oldenlandia chemistry
Subjects
Details
- Language :
- English
- ISSN :
- 1439-4227
- Volume :
- 8
- Issue :
- 9
- Database :
- MEDLINE
- Journal :
- Chembiochem : a European journal of chemical biology
- Publication Type :
- Academic Journal
- Accession number :
- 17534989
- Full Text :
- https://doi.org/10.1002/cbic.200700097