4.8 Article

Convergent Palladium-Catalyzed Stereospecific Arginine Glycosylation Using Glycals

Journal

ORGANIC LETTERS
Volume 23, Issue 10, Pages 4008-4012

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.1c01218

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Funding

  1. National Science Foundation [CHE 1710174]
  2. National Institute of Health [1R35 GM138336-01, CHE 17267240]

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This method allows effective arginine glycosylation, catalyzed by a palladium complex, which can be achieved in one step at room temperature with high functional group tolerance, facilitating the preparation of glycopeptide analogues.
A stereospecific convergent peptide arginine glycosylation method is reported for the first time. A recently discovered arginine glycosylation invigorated the interests of arginine modification, which has been challenging, because of the inertness of the guanidino side chain. The approach renders the arginine glycoside construction convergently. Catalyzed by palladium complex, glycals modify arginine guanidino groups in one step with high functional group tolerance at ambient temperature. The glycosylated products may be converted to glycopeptide analogues in few steps.

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