title: Sequencing of oligourea foldamers by tandem mass spectrometry.
abstract: This study is focused on sequence analysis of peptidomimetic helical oligoureas by means of tandem mass spectrometry, to build a basis for de novo sequencing for future high-throughput combinatorial library screening of oligourea foldamers. After the evaluation of MS/MS spectra obtained for model compounds with either MALDI or ESI sources, we found that the MALDI-TOF-TOF instrument gave more satisfactory results. MS/MS spectra of oligoureas generated by decay of singly charged precursor ions show major ion series corresponding to fragmentation across both CO-NH and N'H-CO urea bonds. Oligourea backbones fragment to produce a pattern of a, x, b, and y type fragment ions. De novo decoding of spectral information is facilitated by the occurrence of low mass reporter ions, representative of constitutive monomers, in an analogous manner to the use of immonium ions for peptide sequencing.
authors: University of Bordeaux, UMR 5248 CNRS-Université Bordeaux-IPB, Bordeaux, France.
authors: Katell
authors: K
authors: Bathany
authors: Neil W
authors: NW
authors: Owens
authors: Gilles
authors: G
authors: Guichard
authors: Jean-Marie
authors: JM
authors: Schmitter
mesh_terms: D000595:Amino Acid Sequence; D008958:Models, Molecular; D057786:Peptidomimetics / Q000737:chemistry*; D017510:Protein Folding; D019032:Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization / Q000379:methods; D053719:Tandem Mass Spectrometry / Q000379:methods; D014508:Urea / Q000737:chemistry*
chemical_list: D057786:Peptidomimetics; D014508:Urea
references: Anal Chem. 2007 Nov 15;79(22):8678-85
references: 17939742
references: Angew Chem Int Ed Engl. 2010;49(2):333-6
references: 19957258
references: J Mass Spectrom. 2005 Nov;40(11):1429-38
references: 16220504
references: J Am Soc Mass Spectrom. 1993 Nov;4(11):882-93
references: 24227532
references: Biomed Mass Spectrom. 1984 Nov;11(11):601
references: 6525415
references: Chem Soc Rev. 2009 Dec;38(12):3289-300
references: 20449049
references: Angew Chem Int Ed Engl. 2002 Jun 3;41(11):1893-5
references: 19750624
references: Chem Biol. 2006 May;13(5):531-8
references: 16720274
references: Chem Commun (Camb). 2011 Jun 7;47(21):5933-41
references: 21483969
references: J Am Chem Soc. 2005 Sep 28;127(38):13271-80
references: 16173757
references: J R Soc Interface. 2006 Apr 22;3(7):215-33
references: 16849232
references: Org Biomol Chem. 2010 Jul 21;8(14):3101-17
references: 20502838
references: J Am Chem Soc. 2005 Feb 23;127(7):2156-64
references: 15713093
references: J Am Chem Soc. 2005 Oct 26;127(42):14584-5
references: 16231906
references: J Mass Spectrom. 2009 Sep;44(9):1338-47
references: 19618398
references: J Comb Chem. 2009 Mar 9;11(2):294-302
references: 19154119
references: Rapid Commun Mass Spectrom. 1996;10(4):459-64
references: 8721042
references: Angew Chem Int Ed Engl. 2010 Feb 1;49(6):1067-70
references: 20039243