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1.
公开(公告)号:US12110309B2
公开(公告)日:2024-10-08
申请号:US16590676
申请日:2019-10-02
申请人: SHIMADZU CORPORATION
发明人: Takashi Nishikaze
CPC分类号: C07H1/00 , G01N33/6848 , G01N2400/00 , G01N2440/38 , G01N2560/00
摘要: A method for preparing an analytical sample for analysis of a glycan contained in a sample includes: performing an amidation reaction that amidates a lactone structure included in the glycan through contacting the sample with a reaction solution that is basic; adding an acidic solution to the reaction solution after the reaction solution is subjected to the amidation reaction; and purifying the sample contained in the reaction solution after the acidic solution is added to the reaction solution by using a carrier for hydrophilic interaction chromatography.
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2.
公开(公告)号:US20220189756A1
公开(公告)日:2022-06-16
申请号:US17644364
申请日:2021-12-15
申请人: SHIMADZU CORPORATION
发明人: Masaki MURASE , Takashi Nishikaze
摘要: In a device for analyzing mass spectrum data of a sample containing a sialic-acid-linked glycan subjected to a sialic-acid-linkage-specific derivatization or a molecule modified with the glycan, a glycan information acquisition section acquires a plurality of kinds of glycans having a core structure formed by a plurality of monosaccharide residues of a plurality of kinds, and mass information corresponding to each of those glycans, based on a glycan composition set through a glycan composition setting section. A mass-changing factor setting section allows a setting of mass-changing factors causing a mass change of a glycan. A theoretical glycan mass calculation section determines a theoretical glycan mass-to-charge ratio after the mass change of the glycan occurs, of each glycan based on the mass-changing factors, which include an ion species or salt that is possibly formed on a carboxyl group of a sialic acid in a sialic-acid-linked glycan included in the analysis target and a sialic-acid linkage type in which a mass change corresponding to the derivatization possibly occurs. A mass change calculation section estimates the mass change from the combination of the ion species or the salt and the sialic-acid linkage type.
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公开(公告)号:US20210208117A1
公开(公告)日:2021-07-08
申请号:US17094912
申请日:2020-11-11
申请人: SHIMADZU CORPORATION
发明人: Masaki Murase , Takashi Nishikaze
摘要: A glycopeptide analyzer that performs a structural analysis on glycoforms of a glycoprotein, including: a spectrum creator creating an MS/MS spectrum for each elution time based on data acquired by an LC/MS analysis of a sample containing glycopeptides originating from a target glycoprotein; a peptide mass calculator selecting a glycopeptide-related spectrum from a plurality of MS/MS spectra and calculating the mass of a peptide from the selected spectrum; a similarity determiner determining a similarity between the glycopeptide-related spectrum and each of the other MS/MS spectra; an elution-time range estimator estimating an elution-time range based on a distribution of the frequency of occurrence of an MS/MS spectrum for which a high level of similarity has been determined on a time axis; and a glycan composition estimator selecting an ion peak corresponding to a mass equal to or greater than a peptide mass and estimating a glycan composition based on the peak.
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公开(公告)号:US11906522B2
公开(公告)日:2024-02-20
申请号:US16347639
申请日:2016-11-07
申请人: SHIMADZU CORPORATION
发明人: Takashi Nishikaze
CPC分类号: G01N33/58 , H01J49/004 , H01J49/0027 , G01N2400/10
摘要: Glycans having a branched structure are labeled with a labeling agent, such as 2-aminobenzoic acid, having one site that is easily negatively charged. At this time, reduction which is usually performed in labeling by reduction amination is not performed. A sample for mass spectrometry containing the labeled form of glycans thus obtained is prepared, and is subjected to MS/MS analysis in negative ion mode. In the MS/MS spectra obtained by the MS/MS analysis, peaks of E ions, D ions and the like which reflect the branched structure clearly appear. As a result, structural analysis of an entirety of the glycan including the branched structure can be easily performed.
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公开(公告)号:US11686713B2
公开(公告)日:2023-06-27
申请号:US17094912
申请日:2020-11-11
申请人: SHIMADZU CORPORATION
发明人: Masaki Murase , Takashi Nishikaze
CPC分类号: G01N30/88 , G01N30/86 , G01N2030/8831 , G01N2440/38 , G01N2560/00 , G01N2570/00
摘要: A glycopeptide analyzer that performs a structural analysis on glycoforms of a glycoprotein, including: a spectrum creator creating an MS/MS spectrum for each elution time based on data acquired by an LC/MS analysis of a sample containing glycopeptides originating from a target glycoprotein; a peptide mass calculator selecting a glycopeptide-related spectrum from a plurality of MS/MS spectra and calculating the mass of a peptide from the selected spectrum; a similarity determiner determining a similarity between the glycopeptide-related spectrum and each of the other MS/MS spectra; an elution-time range estimator estimating an elution-time range based on a distribution of the frequency of occurrence of an MS/MS spectrum for which a high level of similarity has been determined on a time axis; and a glycan composition estimator selecting an ion peak corresponding to a mass equal to or greater than a peptide mass and estimating a glycan composition based on the peak.
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6.
公开(公告)号:US11187630B2
公开(公告)日:2021-11-30
申请号:US16547691
申请日:2019-08-22
申请人: SHIMADZU CORPORATION
发明人: Takashi Nishikaze
摘要: A method for preparing an analytical sample for analyzing a glycan contained in a sample includes: performing a first reaction so that when sialic acid is linked to the glycan, sialic acid of a first linkage type is lactonized and modification different from lactonization is performed on sialic acid of a second linkage type different from the first linkage type; performing a second reaction to ring-open a lactone formed in the first reaction; and performing the first reaction again.
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公开(公告)号:US11971336B2
公开(公告)日:2024-04-30
申请号:US16289643
申请日:2019-02-28
申请人: SHIMADZU CORPORATION
CPC分类号: G01N1/30 , C08B37/0006 , G01N30/06 , G01N33/50 , G01N33/6848 , H01J49/0027 , G01N2400/00
摘要: A method for preparing a sample comprising a glycan includes: performing a lactonization reaction in which at least a part of sialic acids included in the glycan is lactonized; and performing an amidation reaction in which lactones of lactonized sialic acids are amidated through addition of an amidation reaction solution to the sample, the amidation reaction solution comprising at least one selected from the group consisting of ammonia, an amine, and a salt thereof that is reacted with the lactonized sialic acids.
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8.
公开(公告)号:US11105717B2
公开(公告)日:2021-08-31
申请号:US16549020
申请日:2019-08-23
申请人: SHIMADZU CORPORATION
发明人: Takashi Nishikaze
摘要: A method for preparing an analytical sample for analysis of a glycan that includes a lactone structure and is contained in a sample, includes: performing a first amidation reaction that amidates a sialic acid including the lactone structure through addition of a first amidation reaction solution to the sample, the first amidation reaction solution containing ammonia, an amine, or a salt thereof as a first nucleophilic agent that is reacted with the sialic acid including the lactone structure; and performing a second reaction that modifies at least a part of sialic acids not amidated in the first amidation reaction through a method different from permethylation.
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公开(公告)号:US10712338B2
公开(公告)日:2020-07-14
申请号:US15562698
申请日:2016-03-31
申请人: SHIMADZU CORPORATION
发明人: Takashi Nishikaze
摘要: In the method of preparing a sample for analysis, a reaction is performed that produces different modified product depending on the sialic acid linkage type when a sialic acid is bound to a sugar chain of an analyte. In this reaction, an analyte containing a sugar chain, an amine containing two or more carbon atoms, and a dehydration-condensation agent are used. The sialic acid linkage type can be identified by analyzing the resulting sample with mass spectrometry etc. This method is applicable not only to free sugar chains but also to glycopeptides and glycoproteins.
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