title: Site-specific indolation of proline-based peptides via copper(II)-catalyzed oxidative coupling of tertiary amine N-oxides.
abstract: The first site-specific and purely chemical method for modifying proline-based peptides was developed via a convenient, copper-catalyzed oxidative coupling of tertiary amine N-oxides with indoles. This novel approach features high regioselectivity and diastereoselectivity, mild conditions, and compatibility with various functional groups. In addition, a simplified process was realized in one pot and two steps via in situ oxidative coupling of tertiary amine and indoles.
authors.affiliation: CAS Key Laboratory of Receptor Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, 555 Zuchongzhi Road, Shanghai 201203, P. R. China. hliu@mail.shcnc.ac.cn.
authors.forename: Xiaowei
authors.initials: X
authors.lastname: Wu
authors.forename: Dengyou
authors.initials: D
authors.lastname: Zhang
authors.forename: Shengbin
authors.initials: S
authors.lastname: Zhou
authors.forename: Feng
authors.initials: F
authors.lastname: Gao
authors.forename: Hong
authors.initials: H
authors.lastname: Liu
mesh_terms: D000588:Amines / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry; D058451:Oxidative Coupling; D010087:Oxides / Q000737:chemistry*; D010455:Peptides / Q000737:chemistry*; D011392:Proline / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000588:Amines; D007211:Indoles; D010087:Oxides; D010455:Peptides; D003300:Copper; D011392:Proline