[go: up one dir, main page]

WO2004046731A3 - Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivatives - Google Patents

Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivatives Download PDF

Info

Publication number
WO2004046731A3
WO2004046731A3 PCT/US2003/036739 US0336739W WO2004046731A3 WO 2004046731 A3 WO2004046731 A3 WO 2004046731A3 US 0336739 W US0336739 W US 0336739W WO 2004046731 A3 WO2004046731 A3 WO 2004046731A3
Authority
WO
WIPO (PCT)
Prior art keywords
mass
charge
amino acids
protein
fixed charge
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/US2003/036739
Other languages
French (fr)
Other versions
WO2004046731A2 (en
Inventor
Gavin Reid
Richard Simpson
Richard O'hair
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ludwig Institute for Cancer Research Ltd
Ludwig Cancer Research
Original Assignee
Ludwig Institute for Cancer Research Ltd
Ludwig Cancer Research
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ludwig Institute for Cancer Research Ltd, Ludwig Cancer Research filed Critical Ludwig Institute for Cancer Research Ltd
Priority to JP2004553836A priority Critical patent/JP2006506647A/en
Priority to EP03781974A priority patent/EP1565752A2/en
Priority to US10/535,389 priority patent/US20060094121A1/en
Priority to AU2003287673A priority patent/AU2003287673A1/en
Publication of WO2004046731A2 publication Critical patent/WO2004046731A2/en
Anticipated expiration legal-status Critical
Publication of WO2004046731A3 publication Critical patent/WO2004046731A3/en
Ceased legal-status Critical Current

Links

Classifications

    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6848Methods of protein analysis involving mass spectrometry
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6842Proteomic analysis of subsets of protein mixtures with reduced complexity, e.g. membrane proteins, phosphoproteins, organelle proteins
    • GPHYSICS
    • G01MEASURING; TESTING
    • G01NINVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
    • G01N33/00Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
    • G01N33/48Biological material, e.g. blood, urine; Haemocytometers
    • G01N33/50Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
    • G01N33/68Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
    • G01N33/6803General methods of protein analysis not limited to specific proteins or families of proteins
    • G01N33/6848Methods of protein analysis involving mass spectrometry
    • G01N33/6851Methods of protein analysis involving laser desorption ionisation mass spectrometry

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Molecular Biology (AREA)
  • Physics & Mathematics (AREA)
  • Hematology (AREA)
  • Chemical & Material Sciences (AREA)
  • Biomedical Technology (AREA)
  • Urology & Nephrology (AREA)
  • Immunology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Bioinformatics & Computational Biology (AREA)
  • Biophysics (AREA)
  • Analytical Chemistry (AREA)
  • Microbiology (AREA)
  • Biotechnology (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Food Science & Technology (AREA)
  • Medicinal Chemistry (AREA)
  • Cell Biology (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • Pathology (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Optics & Photonics (AREA)
  • Other Investigation Or Analysis Of Materials By Electrical Means (AREA)

Abstract

The invention provides methods, reagents and kits for amino acid, peptide and protein identification, differential quantitation and for the analysis of post translational modification and cross-linking status, comprising: derivatizing a mixture of amino acids peptides or proteins, to form at least one amino acid peptide or protein containing a fixed-charge ion, other than at the C-terminal or N-terminal end thereof; introducing the mixture of amino acids peptides or proteins containing the fixed charge derivatized amino acid peptide or protein to a mass spectrometer; passing the mixture of amino acids peptides or proteins containing the fixed charge derivatized amino acid peptide or protein through a first mass resolving spectrometer to select precursor protein or peptide ions having a first desired mass-to-charge ratio; subjecting the precursor ions of the first mass to charge ratio to dissociation to form a product ion having a second mass-to-charge ratio that is characteristic of a fragmentation occurring at a site adjacent to the fixed charge; and detecting the product ions having the second mass-to-charge ratio. The product ion having the second mass-to-charge ratio may be either a product ion formed by neutral loss of the fixed charge from the precursor ion, or a product ion formed by charged loss of the fixed charge from the precursor ion.
PCT/US2003/036739 2002-11-18 2003-11-18 Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivatives Ceased WO2004046731A2 (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
JP2004553836A JP2006506647A (en) 2002-11-18 2003-11-18 Method for analyzing amino acids, peptides and proteins
EP03781974A EP1565752A2 (en) 2002-11-18 2003-11-18 Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivates
US10/535,389 US20060094121A1 (en) 2002-11-18 2003-11-18 Method for analysing amino acids, peptides and proteins
AU2003287673A AU2003287673A1 (en) 2002-11-18 2003-11-18 Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivatives

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
AU2002952747A AU2002952747A0 (en) 2002-11-18 2002-11-18 Method for analysing peptides
AU2002952747 2002-11-28

Publications (2)

Publication Number Publication Date
WO2004046731A2 WO2004046731A2 (en) 2004-06-03
WO2004046731A3 true WO2004046731A3 (en) 2005-06-23

Family

ID=28796128

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2003/036739 Ceased WO2004046731A2 (en) 2002-11-18 2003-11-18 Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivatives

Country Status (4)

Country Link
EP (1) EP1565752A2 (en)
JP (1) JP2006506647A (en)
AU (1) AU2002952747A0 (en)
WO (1) WO2004046731A2 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9196466B2 (en) 2002-07-24 2015-11-24 Micromass Uk Limited Mass spectrometer with bypass of a fragmentation device

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20020115056A1 (en) 2000-12-26 2002-08-22 Goodlett David R. Rapid and quantitative proteome analysis and related methods
SE0401293D0 (en) * 2004-05-17 2004-05-17 Amersham Biosciences Ab Novel MS Reagents
KR100611313B1 (en) * 2004-06-30 2006-08-10 고려대학교 산학협력단 N-terminal substitution of polypeptide, amino acid sequencing and quantification method in polypeptide
WO2006023398A2 (en) * 2004-08-16 2006-03-02 Ludwig Institute For Cancer Research Modular isotope labelled mass spectrometry reagents and methods for quantitation of amino acids, peptides and proteins
US20090053817A1 (en) * 2004-08-16 2009-02-26 Ludwig Institute For Cancer Research Fixed charge reagents
US20060183238A1 (en) * 2005-02-09 2006-08-17 Applera Corporation Amine-containing compound analysis methods
GB0523806D0 (en) * 2005-11-23 2006-01-04 Micromass Ltd Mass spectrometer
GB0523811D0 (en) * 2005-11-23 2006-01-04 Micromass Ltd Mass stectrometer
WO2008111911A1 (en) * 2007-03-13 2008-09-18 Nanyang Polytechnic System and process for pre-filtering of tandem mass spectra using piecewise convolution
DE602008001609D1 (en) 2007-03-19 2010-08-05 Brains Online Holding B V METHOD FOR DETERMINING AN ANALYTE WITH A PRIMARY AMINO GROUP AND KIT FOR LABELING THIS ANALYSIS
US9202678B2 (en) 2008-11-14 2015-12-01 Board Of Trustees Of Michigan State University Ultrafast laser system for biological mass spectrometry
US8372653B2 (en) * 2010-01-22 2013-02-12 Dh Technologies Development Pte. Ltd. Mass tag reagents for simultaneous quantitation and identification of small molecules
JP5799618B2 (en) * 2011-07-06 2015-10-28 株式会社島津製作所 MS / MS mass spectrometer and program for the same
US9581605B2 (en) 2012-05-22 2017-02-28 Biogen Ma Inc. Trapping reagents for reactive metabolites screening
CN105051530B (en) 2013-03-14 2018-05-01 莱克公司 System and method for Tandem Mass Spectrometry Analysis
EP3023420A1 (en) 2014-11-18 2016-05-25 Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e.V. Methods for providing stable isoindole derivatives
CN110133124A (en) * 2019-04-29 2019-08-16 天津中医药大学 The content assaying method of 18 kinds of amino acid in SHUXUETONG ZHUSHEYE
CN115515928B (en) * 2020-02-28 2024-05-10 公立大学法人大阪 Method for analyzing polysulfide, method for inhibiting hydrolysis of polysulfide, and use of N-iodoacetyl-L-tyrosine methyl ester
CN112786105B (en) * 2020-12-07 2024-05-07 中山大学附属第五医院 A metaproteome mining method and its application in obtaining intestinal microbial proteolytic characteristics

Non-Patent Citations (11)

* Cited by examiner, † Cited by third party
Title
ADAMCZYK MACIEJ ET AL: "Charge derivatization of peptides to simplify their sequencing with an ion trap mass spectrometer", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, vol. 13, no. 14, 1999, pages 1413 - 1422, XP009041623, ISSN: 0951-4198 *
BRANCIA F L ET AL: "IMPROVED MATRIX-ASSISTED LASER DESORPTION/IONIZATION MASS SPECTROMETRIC ANALYSIS OF TRYPTIC HYDROLYSATES OF PROTEINS FOLLOWING GUANIDINATION OF LYSINE-CONTAINING PEPTIDES", RAPID COMMUNICATIONS IN MASS SPECTROMETRY, HEYDEN, LONDON, GB, vol. 14, no. 21, 2000, pages 2070 - 2073, XP009018972, ISSN: 0951-4198 *
GU C ET AL: "Selective gas-phase cleavage at the peptide bond C-terminal to aspartic acid in fixed-charge derivatives of Asp-containing peptides", ANALYTICAL CHEMISTRY 01 DEC 2000 UNITED STATES, vol. 72, no. 23, 1 December 2000 (2000-12-01), pages 5804 - 5813, XP002313095, ISSN: 0003-2700 *
MORIARTY, ROBERT M. ET AL: "Reaction of [hydroxy(tosyloxy)iodo]benzene and [hydroxy(mesyloxy)iodo]benzene with trimethylsilyl enol ethers. A new general method for .alpha.-sulfonyloxylation of carbonyl compounds", JOURNAL OF ORGANIC CHEMISTRY , 54(5), 1101-4 CODEN: JOCEAH; ISSN: 0022-3263, 1989, XP002323781 *
REID G E ET AL: "Leaving group and gas phase neighboring group effects in the side chain losses from protonated serine and its derivatives*", JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, ELSEVIER SCIENCE INC., NEW YORK, NY, US, vol. 11, no. 12, December 2000 (2000-12-01), pages 1047 - 1060, XP004220712, ISSN: 1044-0305 *
SADAGOPAN N ET AL: "Investigation of the tris(trimethoxyphenyl)phosphonium acetyl charged derivatives of peptides by electrospray ionization mass spectrometry and tandem mass spectrometry - Evidence for the mobile proton model", JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, ELSEVIER SCIENCE INC., NEW YORK, NY, US, vol. 11, no. 2, February 2000 (2000-02-01), pages 107 - 119, XP004184664, ISSN: 1044-0305 *
SADAGOPAN N ET AL: "Mass spectrometric evidence for mechanisms of fragmentation of charge-derivatized peptides", JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, ELSEVIER SCIENCE INC., NEW YORK, NY, US, vol. 12, no. 4, April 2001 (2001-04-01), pages 399 - 409, XP004233057, ISSN: 1044-0305 *
SONSMANN G ET AL: "Investigation of the influence of charge derivatization on the fragmentation of multiply protonated peptides", JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, ELSEVIER SCIENCE INC., NEW YORK, NY, US, vol. 13, no. 1, January 2002 (2002-01-01), pages 47 - 58, XP004326923, ISSN: 1044-0305 *
SPENGLER B ET AL: "Peptide sequencing of charged derivatives by postsource decay MALDI mass spectrometry", INTERNATIONAL JOURNAL OF MASS SPECTROMETRY AND ION PROCESSES, ELSEVIER SCIENTIFIC PUBLISHING CO. AMSTERDAM, NL, vol. 169-170, December 1997 (1997-12-01), pages 127 - 140, XP004109239, ISSN: 0168-1176 *
ZAIA J ET AL: "Comparison of Charged Derivatives for High Energy Collision-Induced Dissociation Tandem Mass Spectrometry", JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, ELSEVIER SCIENCE INC, US, vol. 6, no. 5, May 1995 (1995-05-01), pages 428 - 436, XP004052025, ISSN: 1044-0305 *
ZEFIROV, N. S. ET AL: "Oxidatively assisted nucleophilic substitution of iodine in alkyl iodides by nucleofugic anions", JOURNAL OF ORGANIC CHEMISTRY , 50(11), 1872-6 CODEN: JOCEAH; ISSN: 0022-3263, 1985, XP002323780 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9196466B2 (en) 2002-07-24 2015-11-24 Micromass Uk Limited Mass spectrometer with bypass of a fragmentation device

Also Published As

Publication number Publication date
EP1565752A2 (en) 2005-08-24
JP2006506647A (en) 2006-02-23
WO2004046731A2 (en) 2004-06-03
AU2002952747A0 (en) 2002-12-05

Similar Documents

Publication Publication Date Title
WO2004046731A3 (en) Method for analysing amino acids, peptides and proteins using mass spectroscopy of fixed charge-modified derivatives
Breuker et al. Top-down identification and characterization of biomolecules by mass spectrometry
DE60223696T2 (en) GROUND MARKER
Sun et al. Inhibition of protein carbamylation in urea solution using ammonium-containing buffers
US8426155B2 (en) Proteome analysis in mass spectrometers containing RF ion traps
CN103392219A (en) Quantitation of insulin by mass spectrometry
JP2024050535A (en) Detection of amyloid beta by mass spectrometry
DE102012102874A1 (en) Method for analyzing analyte with use of mass spectrometry, involves providing isobaric labeled analyte and generating distribution of precursor ions from isobaric labeled analyte
Samyn et al. A case study of de novo sequence analysis of N-sulfonated peptides by MALDI TOF/TOF mass spectrometry
WO2002008767A2 (en) Methods and kits for sequencing polypeptides
Yates [15] Protein structure analysis by mass spectrometry
Jones et al. Isolation and characterization of conopeptides by high‐performance liquid chromatography combined with mass spectrometry and tandem mass spectrometry
GB2477000A (en) Method for detecting and sequencing post transationally modified peptides
US7729868B2 (en) Method for analyzing structure of glycoprotein
Jiao et al. Hydrazinonicotinic acid derivatization for selective ionization and improved glycan structure characterization by MALDI-MS
GB2443571A (en) Methods of comparing samples in mass spectrometry
WO2001074842A1 (en) Macromolecule detection
Waldera-Lupa et al. The fate of b-ions in the two worlds of collision-induced dissociation
Apffel et al. Application of high-performance liquid chromatography-electrospray ionization mass spectrometry and matrix-assisted laser-desorption ionization time-of-flight mass spectrometry in combination with selective enzymatic modifications in the characterization of glycosylation patterns in single-chain plasminogen activator
Yang et al. A new method for analysis of disulfide-containing proteins by matrix-assisted laser desorption ionization (MALDI) mass spectrometry
Kjeldsen et al. Towards liquid chromatography time-scale peptide sequencing and characterization of post-translational modifications in the negative-ion mode using electron detachment dissociation tandem mass spectrometry
JPWO2002027328A1 (en) Structural analysis of antibody molecules
CA2628927A1 (en) Mass spectrometer
EP3109630A1 (en) Protein detection method using mass spectrometry
US20030104483A1 (en) Liquid chromatography/fourier-transform mass spectrometry/electron capture dissociation for the analysis of proteins

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A2

Designated state(s): AU JP US

AL Designated countries for regional patents

Kind code of ref document: A2

Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IT LU MC NL PT RO SE SI SK TR

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
WWE Wipo information: entry into national phase

Ref document number: 2003781974

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2003287673

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 2004553836

Country of ref document: JP

WWP Wipo information: published in national office

Ref document number: 2003781974

Country of ref document: EP

ENP Entry into the national phase

Ref document number: 2006094121

Country of ref document: US

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 10535389

Country of ref document: US

WWP Wipo information: published in national office

Ref document number: 10535389

Country of ref document: US

WWW Wipo information: withdrawn in national office

Ref document number: 2003781974

Country of ref document: EP