Title:
PHOSPHORYLATED PROTEIN LABELING REAGENT CONTAINING EQUAL-WEIGHT STABLE ISOTOPES, PREPARATION METHOD THEREFOR AND USE THEREOF
Document Type and Number:
WIPO Patent Application WO/2021/208818
Kind Code:
A1
Abstract:
Provided are a phosphorylated protein labeling reagent containing equal-weight stable isotopes, a preparation method therefor and a use thereof. The protein labeling reagent is a phosphorylated dipeptide organophosphorus reagent labeled by stable isotopes containing deuterium-2, carbon-13, oxygen-18, nitrogen-15 etc. The preparation method for the phosphorylated protein labeling reagent comprises: (1) preparing N-terminal protected amino acid containing equal-weight stable isotopes; (2) preparing amino acid activated ester Fmoc/Boc-R1-NHS containing equal-weight stable isotopes; (3) preparing dipeptide containing equal-weight stable isotopes; (4) preparing phosphite ester containing equal-weight stable isotopes; (5) preparing phosphite ester dipeptide containing equal-weight stable isotopes; and (6) preparing the stable isotope labeled N-phosphorylated amino acid activated ester. The protein labeling reagent provided in the present invention can realize quantitative analysis of polypeptides, standard proteins, proteins in cells, and proteins in urine samples and blood samples.
Inventors:
GAO XIANG (CN)
WANG XIAOYU (CN)
HUANG CHENGTING (CN)
ZHAO YUFEN (CN)
WANG XIAOYU (CN)
HUANG CHENGTING (CN)
ZHAO YUFEN (CN)
Application Number:
PCT/CN2021/086224
Publication Date:
October 21, 2021
Filing Date:
April 09, 2021
Export Citation:
Assignee:
GUANGDONG PHOBIOLOGY TECH CO LTD (CN)
International Classes:
C07K1/02; C07K5/062; C07K1/06; C07K1/13; G01N30/06; G01N33/68
Domestic Patent References:
| WO2010120946A1 | 2010-10-21 |
Foreign References:
| CN111499686A | 2020-08-07 | |||
| CN106596967A | 2017-04-26 |
Other References:
ZHANG SHANSHAN, JINWEN SHI, CHANGKAI SHAN, CHENGTING HUANG, YILE WU, RONG DING, YUHUA XUE, WEN LIU, QIANG ZHOU, YUFEN ZHAO, PENGXI: "Stable isotope N-phosphoryl amino acids labeling for quantitative profiling of amine-containing metabolites using liquid chromatography mass spectrometry", ANALYTICA CHIMICA ACTA, vol. 978, 27 April 2017 (2017-04-27), pages 24 - 34, XP055859221, DOI: 10.1016/j.aca.2017.04.025
ONG, S. EMANN, M: "Mass spectrometry-based proteomics turns quantitative", NAT. CHEM. BIOL, vol. 1, 2005, pages 252 - 262, XP002430016, DOI: 10.1038/nchembio736
ROSS, P. LHUANG, Y. NMARCHESE, J. N.;WILLIAMSON, BPARKER, KHATTAN, SKHAINOVSKI, NPILLAI, SDEY, SDANIELS, S: "Multiplexed protein quantitation in Saccharomyces cerevisiae using amine-reactive isobaric tagging reagents", MOL. CELL. PROTEOMICS, vol. 3, 2004, pages 1154 - 1169, XP055533176, DOI: 10.1074/mcp.M400129-MCP200
GYGI, S. PRIST, BGERBER, S. ATURECEK, FGELB, M. H: "Aebersold, R. Quantitative analysis of comlex protein mixtures using isotope-coded affinity tags", NAT. BIOTECHNOL., vol. 17, 1999, pages 994 - 999
THOMPSON, ASCHAFER, JKUHN, KKIENLE, SSCHWARZ, JSCHMIDT, GNEUMANN, THAMON, C: "Tandem mass tags: a novel quantification strategy for comparative analysis of complex protein mixtures by MS/MS", ANAL. CHEM., vol. 75, 2003, pages 1895 - 1904, XP002328688, DOI: 10.1021/ac0262560
WINTER, S. VMEIER, FWICHMANN, CCOX, JMANN, MMEISSNER, F: "EASI-tag enables accurate multiplexed and interference-free MS2-based proteome quantification", NATURE METHODS, vol. 15, 2018, pages 527 - 530, XP036542163, DOI: 10.1038/s41592-018-0037-8
LI, J. MVAN VRANKEN, J. G ET AL.: "TMTpro reagents: a set of isobaric labeling mass tags enables simultaneous proteome-wide measurements across 16 samples", NATURE METHODS, 2020
ZHANG, SSHI, JSHAN, CHUANG, CWU, YDING, RXUE, YLIU, WZHOU, QZHAO, Y: "Stable isotope N-phosphoryl amino acids labeling for quantitative profiling of amine-containing metabolites using liquid chromatography mass spectrometry", ANAL. CHIM. ACTA, vol. 978, 2017, pages 24 - 34, XP055859221, DOI: 10.1016/j.aca.2017.04.025
GAO, XWU, HLEE, K.-CLIU, HZHAO, YCAI, ZJIANG, Y: "Stable isotope N-phosphorylation labeling for peptide de novo sequencing and protein quantification based on organic phosphorus chemistry", ANAL. CHEM. (WASHINGTON, DC, U. S., vol. 84, no. 23, 2012, pages 10236 - 10244
ONG, S. EMANN, M: "Mass spectrometry-based proteomics turns quantitative", NAT. CHEM. BIOL, vol. 1, 2005, pages 252 - 262, XP002430016, DOI: 10.1038/nchembio736
ROSS, P. LHUANG, Y. NMARCHESE, J. N.;WILLIAMSON, BPARKER, KHATTAN, SKHAINOVSKI, NPILLAI, SDEY, SDANIELS, S: "Multiplexed protein quantitation in Saccharomyces cerevisiae using amine-reactive isobaric tagging reagents", MOL. CELL. PROTEOMICS, vol. 3, 2004, pages 1154 - 1169, XP055533176, DOI: 10.1074/mcp.M400129-MCP200
GYGI, S. PRIST, BGERBER, S. ATURECEK, FGELB, M. H: "Aebersold, R. Quantitative analysis of comlex protein mixtures using isotope-coded affinity tags", NAT. BIOTECHNOL., vol. 17, 1999, pages 994 - 999
THOMPSON, ASCHAFER, JKUHN, KKIENLE, SSCHWARZ, JSCHMIDT, GNEUMANN, THAMON, C: "Tandem mass tags: a novel quantification strategy for comparative analysis of complex protein mixtures by MS/MS", ANAL. CHEM., vol. 75, 2003, pages 1895 - 1904, XP002328688, DOI: 10.1021/ac0262560
WINTER, S. VMEIER, FWICHMANN, CCOX, JMANN, MMEISSNER, F: "EASI-tag enables accurate multiplexed and interference-free MS2-based proteome quantification", NATURE METHODS, vol. 15, 2018, pages 527 - 530, XP036542163, DOI: 10.1038/s41592-018-0037-8
LI, J. MVAN VRANKEN, J. G ET AL.: "TMTpro reagents: a set of isobaric labeling mass tags enables simultaneous proteome-wide measurements across 16 samples", NATURE METHODS, 2020
ZHANG, SSHI, JSHAN, CHUANG, CWU, YDING, RXUE, YLIU, WZHOU, QZHAO, Y: "Stable isotope N-phosphoryl amino acids labeling for quantitative profiling of amine-containing metabolites using liquid chromatography mass spectrometry", ANAL. CHIM. ACTA, vol. 978, 2017, pages 24 - 34, XP055859221, DOI: 10.1016/j.aca.2017.04.025
GAO, XWU, HLEE, K.-CLIU, HZHAO, YCAI, ZJIANG, Y: "Stable isotope N-phosphorylation labeling for peptide de novo sequencing and protein quantification based on organic phosphorus chemistry", ANAL. CHEM. (WASHINGTON, DC, U. S., vol. 84, no. 23, 2012, pages 10236 - 10244
Attorney, Agent or Firm:
MERITS & TREE (CN)
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