N-terminal labeling of proteins by the Pictet–Spengler reaction

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Abstract

The Pictet–Spengler reaction was applied to the N-terminal labeling of horse heart myoglobin. This was performed in the following two steps: (1) conversion of the N-terminal glycine residue to an α-keto aldehyde by a transamination reaction and (2) condensation of the resulting activated myoglobin with tryptamine analogues by the Pictet–Spengler reaction. Ultraviolet (UV)/visible (vis) absorption and circular dichroism (CD) spectral data revealed that the tertiary structure of myoglobin was not altered by the Pictet–Spengler reaction.

Graphical abstract

This work describes the methodology for the N-terminal modification of proteins by the Pictet–Spengler reaction.

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Acknowledgments

We are grateful to Prof. Hiroshi Nishihara and Dr. Shoko Kume of the University of Tokyo, for help in measuring MALDI mass spectra and to Masaru Kinugawa of the University of Tokyo for help in measuring NMR spectra. Thanks are also due to Prof. Shigeyuki Yokoyama, Dr. Takuhiro Ito and Shinya Mimasu of the University of Tokyo, for help in HPLC purification and UV/vis absorption measurement and to Dr. Hiroshi Nakayama of RIKEN for valuable suggestion. This work was partly supported by a

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