We present novel polyethyleneglycol (PEG) a-hydroxy aldehyde reagents which can be conjugated to amine-containing compounds such as proteins to form stable conjugates in a single-step reaction. These novel aldehyde reagents do not require reductive amination in order to provide a stable conjugate and thus eliminate the need for using sodium cyanoborohydride in protein conjugation reactions. The a-hydroxy aldehyde moiety provides a stable keto-amine conjugate via the Amadori rearrangement. Related Amadori products are known to form in vivo where for example glucose reacts with N-terminal chains of hemoglobin via the Maillard reaction pathway to produce the HbA1c form often used for monitoring long term glucose control. The polymeric reagent may optionally incorporate an internal proton abstracting (basic) functional group, to promote more efficient reaction. Also provided are methods of using the reagents to form conjugates with biologically active compounds.

Novel polyethyleneglycol-aldehyde reagents for amine conjugation via rearrangement

246th National Meeting (2013)

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