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Compatibility of the S- (3-nitro-2-pyridinesulfenyl) protecting group with DCC/HOBt coupling chemistry

Matsueda, R.; Higashida, S.; Albericio, F.; Andreu, D.

Peptide Research 5(5): 262-264

1992

ISSN/ISBN: 1040-5704
PMID: 1450520
Document Number: 391992
Two recent reports on the partial lability of the 3-nitro-2-pyridinesulfenyl (Npys) thiol protecting group towards 1-hydroxybenzotriazole (HOBt) have prompted a rechecking of the chemical behavior of this group. Using both soluble and polymer-bound forms of Cys(Npys) as test materials, the complete stability of this protection against HOBt has now been defintively established, and its compatibility with Boc-benzyl-based solid-phase synthesis strategies has been clearly confirmed by stability assays against a wide range of reagents, as well as by the successful synthesis of several Cys(Npys)-containing peptides.

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