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Stereoselective synthesis of UDP-2-(2-ketopropyl)galactose aided by di-tert-butylsilylene protecting group


UDP-2-(2-ketopropyl)galactose (1) has been utilized as a valuable probe for profiling proteins modified by O-GlcNAc. In this work, we developed a protocol for efficient synthesis of 1. Thus, 2-methallylgalactose derivative 11, a synthetic intermediate for the compound 1, was prepared by stereoselective iodination and methallylation at C-2 position, through exploitation of 4,6-O-di-tert-butylsilylene protecting group.

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electrospray ionization






O-linked β-N-acetylglucosamine hydrolase


O-linked β-N-acetylglucosamine


O-linked β-N-acetylglucosamine transferase


polyethylene glycol






uridine diphosphate


uridine monophosphate


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We thank Dr. Yayoi Hongo and Dr. Takemichi Nakamura for ESI mass measurements. We also thank Ms. Akemi Takahashi and Ms. Satoko Shirahata for technical assistance. This research was supported by the Advanced Research for Medical Products Mining Program (09–01) of the National Institute of Biomedical Innovation, Osaka, Japan (NIBIO).

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Correspondence to Yasuharu Sakamoto or Yukishige Ito.

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Sakamoto, Y., Ohta, T. & Ito, Y. Stereoselective synthesis of UDP-2-(2-ketopropyl)galactose aided by di-tert-butylsilylene protecting group. Glycoconj J 32, 541–548 (2015).

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