PMID: 12782038Jun 5, 2003Paper

Expression of Viola cyclotides by liquid chromatography-mass spectrometry and tandem mass spectrometry sequencing of intercysteine loops after introduction of charges and cleavage sites by aminoethylation

Analytical Biochemistry
Ulf GöranssonPer Claeson

Abstract

The expression of cyclotides-macrocyclic plant peptides-was profiled in six violets, Viola cotyledon, V. biflora, V. arvensis, V. tricolor, V. riviniana, and V. odorata, by LC-MS. All were found to express notably complex mixtures, with single species containing >50 cyclotides. To facilitate their sequencing by MS-MS, an analytical strategy is presented involving aminoethylation of cysteines. This overcomes a number of problems intimately associated with the cyclotide core structure-that is, their joined N and C termini, disulfide knot, and low or clustered content of positively charged amino acids and enzymatic cleavage sites. As a result, charges as well as cleavage sites are introduced at the most conserved part of their sequence, the cysteines. Combined with tryptic digestion, all intercysteine loops are then of suitable size and charge for MS-MS sequencing. The utility of this strategy is shown by the sequencing of two novel cyclotides isolated from V. cotyledon; vico A (cyclo-(AESCVYIPCFTGIAGCSCKNKVCYYNGSIPC)) and vico B (cyclo-(AESCVYIPCITGIAGCSCKNKVCYYNGSIPC)); their complete sequence could be determined by nanospray MS-MS. The strategy for converting conserved cysteines to enzymatic cleavage sites might also benefit th...Continue Reading

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Citations

Sep 1, 2015·ACS Chemical Biology·Anjaneya S RavipatiDavid J Craik
May 26, 2016·Journal of Experimental Botany·Joachim Weidmann, David J Craik
Apr 24, 2016·Biopolymers·Johannes Koehbach, Richard J Clark
Nov 24, 2004·FEBS Letters·Shane M SimonsenDavid J Craik
Nov 5, 2003·Journal of Mass Spectrometry : JMS
Dec 12, 2003·Phytochemical Analysis : PCA
Jun 14, 2006·Journal of Mass Spectrometry : JMS·Alexandr JegorovVladimir Havlicek
May 31, 2007·Chembiochem : a European Journal of Chemical Biology·Manuel Rey R PlanDavid J Craik
Jan 6, 2009·Journal of Forensic Sciences·Eric S WisniewskiEsther W Chege
May 23, 2009·Organic & Biomolecular Chemistry·Manuela TrabiDavid J Craik
Jul 2, 2009·Alzheimer Disease and Associated Disorders·Alexander Frizell SantilloLena Kilander
Aug 12, 2010·Phytochemistry Reviews : Proceedings of the Phytochemical Society of Europe·Lars BohlinAnders Backlund
Jun 22, 2010·Biopolymers·Michelle L ColgraveDavid J Craik
Jun 22, 2010·Biopolymers·Quentin Kaas, David J Craik
Sep 10, 2003·The Journal of Biological Chemistry·Ulf Göransson, David J Craik
Aug 26, 2004·The Journal of Biological Chemistry·Julie L DuttonDavid J Craik
Aug 31, 2004·Journal of Natural Products·Ulf GöranssonLars Bohlin
Dec 18, 2007·Journal of Natural Products·Conan K L WangDavid J Craik
Jun 19, 2008·Journal of Agricultural and Food Chemistry·Manuel Rey R PlanDavid J Craik
Apr 30, 2011·The Journal of Organic Chemistry·David J Craik, Anne C Conibear
Aug 20, 2010·Journal of Natural Products·David C IrelandDavid J Craik
Jun 26, 2010·Journal of Natural Products·Samantha L GerlachUlf Göransson
Feb 18, 2014·Journal of Natural Products·Robert BurmanUlf Göransson
May 15, 2018·Journal of Natural Products·Meri Emili F PintoVanderlan S Bolzani
Mar 9, 2006·Chemical Reviews·Ning-Hua Tan, Jun Zhou
May 29, 2004·Journal of Natural Products·Manuela TrabiLars Bohlin
Jan 31, 2006·Journal of Natural Products·Bin ChenDavid J Craik

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