JP4232660B2 - ペプチドのアミノ酸配列決定法 - Google Patents
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- LLIANSAISVOLHR-GBCQHVBFSA-N 5-[(3as,4s,6ar)-2-oxidanylidene-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]pentanoic acid Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21.N1C(=O)N[C@@H]2[C@H](CCCCC(=O)O)SC[C@@H]21 LLIANSAISVOLHR-GBCQHVBFSA-N 0.000 description 1
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- SJYQYOVTHISIKX-UHFFFAOYSA-N n,n-dimethylformamide;n-ethyl-n-propan-2-ylpropan-2-amine Chemical compound CN(C)C=O.CCN(C(C)C)C(C)C SJYQYOVTHISIKX-UHFFFAOYSA-N 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 229960004072 thrombin Drugs 0.000 description 1
- 239000012588 trypsin Substances 0.000 description 1
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- 108010052257 tyrosyl-isoleucyl-glycyl-seryl-argininamide Proteins 0.000 description 1
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- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6842—Proteomic analysis of subsets of protein mixtures with reduced complexity, e.g. membrane proteins, phosphoproteins, organelle proteins
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01N—INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES
- G01N33/00—Investigating or analysing materials by specific methods not covered by groups G01N1/00 - G01N31/00
- G01N33/48—Biological material, e.g. blood, urine; Haemocytometers
- G01N33/50—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing
- G01N33/68—Chemical analysis of biological material, e.g. blood, urine; Testing involving biospecific ligand binding methods; Immunological testing involving proteins, peptides or amino acids
- G01N33/6803—General methods of protein analysis not limited to specific proteins or families of proteins
- G01N33/6848—Methods of protein analysis involving mass spectrometry
- G01N33/6851—Methods of protein analysis involving laser desorption ionisation mass spectrometry
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- Bioinformatics & Computational Biology (AREA)
- Hematology (AREA)
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- Biomedical Technology (AREA)
- Urology & Nephrology (AREA)
- Immunology (AREA)
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- Analytical Chemistry (AREA)
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- Proteomics, Peptides & Aminoacids (AREA)
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- Other Investigation Or Analysis Of Materials By Electrical Means (AREA)
Description
前記保護されたアミノ酸誘導体が結合したペプチド又はペプチド断片を質量分析法に供することによってペプチドのアミノ酸配列を決定する方法。
なお、本明細書においてペプチドとは、タンパク質を含む意味で用いる。
(2)前記酸性基が、カルボキシル基、スルホ基、ホスホノ基、硫酸基、及びリン酸基からなる群から選ばれる、(1)に記載のペプチドのアミノ酸配列を決定する方法。
(3)前記アミノ酸が、システイン酸、アスパラギン酸、グルタミン酸、リン酸化スレオニン、リン酸化セリン、硫酸化チロシン、及びリン酸化チロシンからなる群から選ばれる、(1)又は(2)に記載のペプチドのアミノ酸配列を決定する方法。
(4)前記保護基が、ビオチニル基、アセチル基、ホルミル基、及びフェニルイソチオカルバミル基からなる群から選ばれる、(1)〜(3)のいずれかに記載のペプチドのアミノ酸配列を決定する方法。
(5)前記保護基がビオチニル基である、(1)〜(3)のいずれかに記載のペプチドのアミノ酸配列を決定する方法。
(6)前記保護されたアミノ酸誘導体がN−ビオチニルシステイン酸である、(1)に記載のペプチドのアミノ酸配列を決定する方法。
(8)前記保護されたアミノ酸誘導体が結合したペプチド又はペプチド断片をイオン化させると共に分解イオンを発生させ、質量分析法により分離検出する、(1)〜(7)のいずれかに記載のペプチドのアミノ酸配列を決定する方法。
(9)前記保護されたアミノ酸誘導体が結合したペプチド又はペプチド断片をマトリックス支援レーザー脱離イオン化法(MALDI)によってイオン化させる、(8)に記載のペプチドのアミノ酸配列を決定する方法。
(10)飛行時間型質量分析法(TOFMS)によって、イオンを分離検出する、(8)又は(9)に記載のペプチドのアミノ酸配列を決定する方法。
スルホスクシンイミドビオチン3.4mgを20μlの蒸留水に溶解したもの、システイン酸1.1mgを15μlの蒸留水に溶解したもの、及び1.65μlのトリエチルアミンを混合し、60℃で30分間反応させた。反応生成物を逆相HPLCで精製し、目的のN−ビオチニルシステイン酸をMALDI−TOF MSで確認した。
モデルペプチドとしてラミニンペンタペプチド((株)ペプチド研究所社製)を用いた。ラミニンペンタペプチドのアミノ酸配列は、Tyr-Ile-Gly-Ser-Arg-NH2である。上記配列においては、アルギニン残基がアミド化されており、アミド化されたアルギニン残基をArg-NH2と表している。1mM N−ビオチニルシステイン酸のジメチルホルムアミド溶液2μl、0.5M HBTU(2-[1H-benzotriazole-1-yl]-1,1,3,3-tetramethyl uronium hexafluorophosphate)と0.5MHOBt(N-hydroxybenzotriazole)とを含むジメチルホルムアミド溶液0.6μl、及び1M ジイソプロピルエチルアミンのジメチルホルムアミド溶液0.6μlを予め混合し、2mM ラミニンペンタペプチドのジメチルホルムアミド溶液2μlに加え、室温で30分間反応を行った。反応終了後、反応溶液を0.1重量%トリフルオロ酢酸水溶液で希釈し、MALDI−TOF MSによってPSD分析を行った。
Claims (10)
- 解析すべきペプチド、又は前記解析すべきペプチドを断片化して得られたペプチド断片のN末端に、側鎖に酸性基を有するアミノ酸のアミノ基が保護基で保護されたアミノ酸誘導体を反応させ、前記保護されたアミノ酸誘導体が結合したぺプチド又はペプチド断片を得て、
前記保護されたアミノ酸誘導体が結合したペプチド又はペプチド断片を質量分析法に供することによってペプチドのアミノ酸配列を決定する方法。 - 前記酸性基が、カルボキシル基、スルホ基、ホスホノ基、硫酸基、及びリン酸基からなる群から選ばれる、請求項1に記載のペプチドのアミノ酸配列を決定する方法。
- 前記アミノ酸が、システイン酸、アスパラギン酸、グルタミン酸、リン酸化スレオニン、リン酸化セリン、硫酸化チロシン、及びリン酸化チロシンからなる群から選ばれる、請求項1又は2に記載のペプチドのアミノ酸配列を決定する方法。
- 前記保護基が、ビオチニル基、アセチル基、ホルミル基、及びフェニルイソチオカルバミル基からなる群から選ばれる、請求項1〜3のいずれか1項に記載のペプチドのアミノ酸配列を決定する方法。
- 前記保護基がビオチニル基である、請求項1〜3のいずれか1項に記載のペプチドのアミノ酸配列を決定する方法。
- 前記保護されたアミノ酸誘導体がN−ビオチニルシステイン酸である、請求項1に記載のペプチドのアミノ酸配列を決定する方法。
- 前記断片化を、塩基性アミノ酸残基のC末端側のペプチド結合を特異的に加水分解する酵素を用いて行う、請求項1〜6のいずれか1項に記載のペプチドのアミノ酸配列を決定する方法。
- 前記保護されたアミノ酸誘導体が結合したペプチド又はペプチド断片をイオン化させると共に分解イオンを発生させ、質量分析法により分離検出する、請求項1〜7のいずれか1項に記載のペプチドのアミノ酸配列を決定する方法。
- 前記保護されたアミノ酸誘導体が結合したペプチド又はペプチド断片をマトリックス支援レーザー脱離イオン化法(MALDI)によってイオン化させる、請求項8に記載のペプチドのアミノ酸配列を決定する方法。
- 飛行時間型質量分析法(TOFMS)によって、イオンを分離検出する、請求項8又は9に記載のペプチドのアミノ酸配列を決定する方法。
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