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2005
Peptides
U 0400
08- 196
Site-Selective Conjugation of Thiols with Aziridine-2-carboxylic Acid-Containing
Peptides. — A series of title tripeptides reacts with thiols (II) in the presence of catalytic amounts of DBU to give α-amino acid products (III) with good yields and high
regioselectivities. The reactions with the carbohydrate thiol proceed with retention of
both the α-anomeric configuration of the thiol and the L-configuration of the newly
generated cysteine derivative. The method is also adapted to solid-phase peptide synthesis, in which incorporation of the aziridine-carboxylic acid residue into peptides and
their ligation with thiols are effected on a solid support. — (GALONIC, D. P.; VAN
DER DONK*, W. A.; GIN, D. Y.; J. Am. Chem. Soc. 126 (2004) 40, 12712-12713;
Dep. Chem., Univ. Ill., Urbana, IL 61801, USA; Eng.) — Klein
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