Open AccessConvergent Palladium-Catalyzed Stereospecific Arginine Glycosylation Using Glycals
Author(s) -
Jun Yang,
Yuanwei Dai,
Rosemarie Bartlett,
Qiang Zhang
Publication year - 2021
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.1c01218
Subject(s) - chemistry , glycosylation , stereospecificity , arginine , glycopeptide , palladium , stereochemistry , catalysis , glycoside , biochemistry , combinatorial chemistry , amino acid , antibiotics
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.