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Development of the Thiol‐Selective Solid‐Supported Oligoarginine‐Conjugating Reagent KSH‐2
Author(s) -
Fukumoto Kentarou,
Kajiyama Akihiro,
Shimura Shunsuke,
Taketa Koji,
Kimura Shinichiro,
Taguchi Akihiro,
Takayama Kentaro,
Yakushiji Fumika,
Hayashi Yoshio
Publication year - 2015
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201500267
Subject(s) - chemistry , reagent , thiol , combinatorial chemistry , membrane , molecule , conjugated system , cysteine , organic chemistry , biochemistry , enzyme , polymer
Arginine‐rich, cell‐penetrating peptides (CPPs) and oligoarginines are attractive tools for intracellular delivery of various molecules with low membrane permeability. Although a variety of labeling methods have been reported, we report here the design and synthesis of a thiol (SH)‐group selective solid‐supported octaarginine‐conjugating reagent KSH‐2. KSH‐2 was prepared by two steps including the activation of 3‐nitro‐2‐pyridinesulfenyl (Npys) resin by chlorosulfenylation and the loading of a Cys( t Bu)‐containing octaarginine unit to form an active disulfide. In model experiments using SH‐containing captopril and hexadecapeptide, solid‐supported reagent KSH‐2 efficiently gave the octaarginine‐conjugated products with a high degree of purity by only mixing and filtration. This reagent could be applied to a wide variety of SH‐containing molecules for selective oligoarginine conjugation.