(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal → HCID 131732956, compound

Participants

Reaction Conditions

Reaction Steps

Glucose was modified with PEG-conjugated to BODIPY. BODIPY was used as a red fluorescent indicator for cell imaging. A flame dried reaction vial (2 mL) was charged with a solution of glucose-PEG-NH2 (32 mg, 0.1 mmol) and BODIPY 650/665-X (64 mg, 0.1 mmol) under argon, and the mixture was cooled in an ice bath at 0° C. Dry dimethylformamide (DMF; Aldrich, 1 mL) was added dropwise and was stirred at 0° C. for 2 h under argon. The reaction mixture was then brought to room temperature, and continuously stirred for 24 h under argon in the dark. The reaction was monitored by reverse-phase high-pressure liquid chromatography (HPLC; Waters Corporation, USA). After completion of the reaction, DMF was removed under reduced pressure and the blue residue was purified by reverse-phase flash column chromatography using a Combiflash separating system (ISCO Combiflash Companion, USA). The desired fractions were collected and lyophilized to obtain the FR-BODIPY-glucose as a bluish green solid (75 mg, 90%). The final compound was soluble in deionized (DI) water and in a mixture of ethanol and water (volume ratio=1:1). Mass spectral analysis showed a molecular ion peak of 841 (M+1). The structure of glucose-PEG-BODIPY is shown in FIG. 1 and the synthesis scheme, including the preparation of glucose-PEG-NH2, is depicted in FIG. 4.

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