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Convergent Palladium-Catalyzed Stereospecific Arginine Glycosylation Using Glycals.

ABSTRACT: 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.

SUBMITTER: Yang J

PROVIDER: S-EPMC8173538 | biostudies-literature | 2021 May

REPOSITORIES: biostudies-literature

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Convergent Palladium-Catalyzed Stereospecific Arginine Glycosylation Using Glycals.

Yang Jun J Dai Yuanwei Y Bartlett Ryan R Zhang Qiang Q

Organic letters 20210512 10

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 gl ...[more]

PMID: 33979173

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