Compatibility of the S-(3-nitro-2-pyridinesulfenyl) protecting group with DCC/HOBt coupling chemistry.
Two recent reports on the partial lability of the 3-nitro-2-pyridinesulfenyl (Npys) thiol protecting group towards 1-hydroxy-benzotriazole (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 definitively 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.
Matsueda
R
R
New Lead Research Laboratories, Sankyo Co., Ltd. Tokyo, Japan.
Higashida
S
S
Albericio
F
F
Andreu
D
D
D000595:Amino Acid Sequence; D004024:Dicyclohexylcarbodiimide / Q000737:chemistry*; D008969:Molecular Sequence Data; D010455:Peptides / Q000138:chemical synthesis; D011725:Pyridines / Q000737:chemistry*; D014230:Triazoles / Q000737:chemistry*
D010455:Peptides; D011725:Pyridines; D014230:Triazoles; D004024:Dicyclohexylcarbodiimide; C065586:3-nitro-2-pyridinesulfenyl; C011852:1-hydroxybenzotriazole