Uranyl Photocleavage of Phosphopeptides Yields Truncated C-Terminally Amidated Peptide Products
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Uranyl Photocleavage of Phosphopeptides Yields Truncated C-Terminally Amidated Peptide Products. / Elnegaard, Rasmus L B; Møllegaard, Niels Erik; Zhang, Qiang; Kjeldsen, Frank; Jørgensen, Thomas J D.
In: ChemBioChem, Vol. 18, No. 12, 19.06.2017, p. 1117-1122.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Uranyl Photocleavage of Phosphopeptides Yields Truncated C-Terminally Amidated Peptide Products
AU - Elnegaard, Rasmus L B
AU - Møllegaard, Niels Erik
AU - Zhang, Qiang
AU - Kjeldsen, Frank
AU - Jørgensen, Thomas J D
N1 - © 2017 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA.
PY - 2017/6/19
Y1 - 2017/6/19
N2 - The uranyl ion (UO2(2+) ) binds phosphopeptides with high affinity, and when irradiated with UV-light, it can cleave the peptide backbone. In this study, high-accuracy tandem mass spectrometry and enzymatic assays were used to characterise the photocleavage products resulting from the uranyl photocleavage reaction of a tetraphosphorylated β-casein model peptide. We show that the primary photocleavage products of the uranyl-catalysed reaction are C-terminally amidated. This could be of great interest to the pharmaceutical industry, as efficient peptide amidation reactions are one of the top challenges in green pharmaceutical chemistry.
AB - The uranyl ion (UO2(2+) ) binds phosphopeptides with high affinity, and when irradiated with UV-light, it can cleave the peptide backbone. In this study, high-accuracy tandem mass spectrometry and enzymatic assays were used to characterise the photocleavage products resulting from the uranyl photocleavage reaction of a tetraphosphorylated β-casein model peptide. We show that the primary photocleavage products of the uranyl-catalysed reaction are C-terminally amidated. This could be of great interest to the pharmaceutical industry, as efficient peptide amidation reactions are one of the top challenges in green pharmaceutical chemistry.
KW - Amides
KW - Amino Acid Sequence
KW - Carboxypeptidases
KW - Caseins
KW - Cations, Divalent
KW - Enzyme Assays
KW - Green Chemistry Technology
KW - Phosphopeptides
KW - Photolysis
KW - Protein Binding
KW - Tandem Mass Spectrometry
KW - Ultraviolet Rays
KW - Uranium Compounds
KW - Journal Article
U2 - 10.1002/cbic.201700103
DO - 10.1002/cbic.201700103
M3 - Journal article
C2 - 28425166
VL - 18
SP - 1117
EP - 1122
JO - ChemBioChem
JF - ChemBioChem
SN - 1439-4227
IS - 12
ER -
ID: 181383513