Amino acids: Optimization in underivatized formula and fragment patterns in LC/ESI-MS analysis. Yoshinori Takano (JAMSTEC)
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1 (a) Positive ion mode (ph < 7) Amino acids: ptimization in underivatized formula and fragment patterns in L/ESI-MS analysis R 1 R 2 N + HA R 3 Base Acid R 1 R N H + 2 R 3 + A - Sample [M + H] + (b) Negative ion mode (ph > 7) R H + B R - + H B + Acid Base Sample [M - H] - Yoshinori Takano (JAMSTE) The principles of acid-base theory in solution chemistry for ESI-MS optimization.
2 (a) Protein AAs (b) Non-protein AAs His, [M+H] + = 156 Met, [M+H] + = 150 Tyr, [M+H] + = 182 Phe, [M+H] + = 166 Arg, [M+H] + = Norleu, [M+H] + = 132 Norval, [M+H] + = 118 α-aaa, [M+H] + = 162 Isoval, [M+H] + = 118 α-aba, [M+H] + = 104 Leu, [M+H] + = 132 γ-aba, [M+H] + = 104 Lys, [M+H] + = 147 α-aiba, [M+H] + = 104 Val, [M+H] + = 118 β-aiba, [M+H] + = 104 Glu, [M+H] + = 148 N-Et-Gly, [M+H] + = 104 Pro, [M+H] + = 116 (Phe) β-ala, [M+H] + = 90 Asp, [M+H] + = 134 Sar, [M+H] + = 90 Thr, [M+H] + = 120 Hyp, [M+H] + = 132 Ala, [M+H] + = 90 Time (min) (c) Unhydrolyzed protein AAs Ser, [M+H] + = 106 Gly, [M+H] + = 76 Time (min) Gln, [M+H] + = 147 (Glu) Asn, [M+H] + = 133 (Asp) Time (min)
3 (a) Protein AAs Gly, [M+H] + = 76 Asp, [M+H] + = 134 H H hemical Formula: 2 H 5 N 2 Exact Mass: Molecular Weight: [M+H-H 2 ] + H H hemical Formula: 4 H 7 N 4 Exact Mass: Molecular Weight: Ser, [M+H] + = 106 Pro, [M+H] + = 116 [M+H-H 2 ] + H H hemical Formula: 3 H 7 N 3 Exact Mass: Molecular Weight: HN H hemical Formula: 5 H 9 N 2 Exact Mass: Molecular Weight: Ala, [M+H] + = 90 H Glu, [M+H] + = 148 H hemical Formula: 3 H 7 N 2 Exact Mass: Molecular Weight: [M+H-H 2-46] + [M+H-H 2 ] + H hemical Formula: 5 H 9 N 4 Exact Mass: Molecular Weight: Thr, [M+H] + = 120 Val, [M+H] + = 118 [M+H-H 2 ] + H H H hemical Formula: 4 H 9 N 3 Exact Mass: Molecular Weight: H H 3 hemical Formula: 5 H 11 N 2 Exact Mass: Molecular Weight:
4 H Lys, [M+H] + = 147 H Arg, [M+H] + = 175 hemical Formula: 6 H 14 N 2 2 Exact Mass: Molecular Weight: NH hemical Formula: 6 H 14 N 4 2 Exact Mass: Molecular Weight: NH H H 3 Leu, [M+H] + = 132 hemical Formula: 6 H 13 N 2 Exact Mass: Molecular Weight: H Phe, [M+H] + = 166 hemical Formula: 9 H 11 N 2 Exact Mass: Molecular Weight: H Met, [M+H] + = 150 H Tyr, [M+H] + = 182 S hemical Formula: 5 H 11 N 2 S Exact Mass: Molecular Weight: H hemical Formula: 9 H 11 N 3 Exact Mass: Molecular Weight: N H His, [M+H] + = 156 hemical Formula: 6 H 9 N 3 2 Exact Mass: Molecular Weight: HN H Hyp, [M+H] + = 132 hemical Formula: 5 H 9 N 3 Exact Mass: Molecular Weight: NH H
5 (b) Non-protein AAs Asn, [M+H] + = 133 Sar, [M+H] + = 90 H hemical Formula: 4 H 8 N 2 3 Exact Mass: Molecular Weight: H 3 NH H hemical Formula: 3 H 7 N 2 Exact Mass: Molecular Weight: Gln, [M+H] + = 147 -Ala, [M+H] + = 90 [M+H-46 -NH 3 ] + H hemical Formula: 5 H 10 N 2 3 Exact Mass: Molecular Weight: [M+H-H 2 ] + H hemical Formula: 3 H 7 N 2 Exact Mass: Molecular Weight: N-Et-Gly, [M+H] + = H 5 NH H hemical Formula: 4 H 9 N 2 Exact Mass: AiBA, [M+H] + = 104 H 2 H hemical Formula: 4 H 9 N 2 Exact Mass:
6 -AiBA, [M+H] + = 104 H -AAA, [M+H] + = 162 H 3 hemical Formula: 4 H 9 N 2 H Exact Mass: [M+H-H 2 ] + H hemical Formula: 6 H 11 N 4 Exact Mass: Molecular Weight: ABA, [M+H] + = 104 Norval, [M+H] + = 118 H 2 H hemical Formula: 4 H 9 N 2 Exact Mass: H hemical Formula: 5 H 11 N 2 Exact Mass: Molecular Weight: H -ABA, [M+H] + = 104 hemical Formula: 4 H 9 N 2 Exact Mass: H Norleu, [M+H] + = 132 hemical Formula: 6 H 13 N 2 Exact Mass: Molecular Weight: Isoval, [M+H] + = 118 hemical Formula: H 5 H 11N 2 Exact Mass: Molecular Weight:
7 (a) -H fragment [M + H - 46] + R H H [M + H] + (b) - fragment [M + H - NH 3 ] + H R' H [M + H] + (c) -H fragment H R" H [M + H - H 2 ] + H [M + H] +
8 Application to L x G//IRMS method: Liquid hromatography x Gas hromatography/ ombustion/ Isotope Ratio Mass Spectrometry R H Amino acid A B D L G IRMS (1D-separation) (2D-separation) magnet ion source A B furnaces m/z D N 2 ion source ESI-MS Identification and determination Preparative collection on a arbitrary purpose High precision measurement of amino acids for 15 N/ 14 N ompound-specific 15 N/ 14 N analysis Takano et al., IJMS (2015)
9 References Takano, Y., hikaraishi, Y. and hkouchi, N. (2015) Isolation of underivatized amino acids by ion-pair high performance liquid chromatography for precise measurement of nitrogen isotopic composition of amino acids: development of comprehensive L x G//IRMS method. International Journal of Mass Spectrometry, 379, doi: /j.ijms hkouchi, N. and Takano, Y. (2014) rganic nitrogen: sources, fates, and chemistry. Treatise on Geochemistry, Vol. 12, 10: rganic Geochemistry (Edited by Birrer, B., Falkowski, P., Freeman, K.), Elsevier, pp doi: /B hikaraishi Y., Takano Y., gawa. N., and hkouchi, N. (2010) Instrumental optimization for compound-specific nitrogen isotope analysis of amino acids by gas chromatography/combustion/ isotope ratio mass spectrometry. Earth, Life, and Isotopes (edited by N. hkouchi, I. Tayasu, and K. Koba). Kyoto University Press., pp Takano, Y., Kashiyama, Y., gawa,.n., hikaraishi, Y., and hkouchi, N., (2010) Isolation and desalting with cation-exchange chromatography for compound-specific nitrogen isotope analysis of amino acids. Rapid ommunications in Mass Spectrometry, 24, doi: /rcm Takano, Y., hikaraishi, Y., gawa,. N., Kitazato, H., and hkouchi, N. (2009) ompound-specific nitrogen isotope analysis of D-alanine, L-alanine, and valine: application of diastereomer separation to delta 15 N and microbial peptidoglycan studies. Analytical hemistry, 81, doi: / ac802077v.
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