Development of the Thiol‐Selective Solid‐Supported Oligoarginine‐Conjugating Reagent KSH‐2. Issue 10 (31st August 2015)

• Record Type: Journal Article
• Authors: Fukumoto, Kentarou; Kajiyama, Akihiro; Shimura, Shunsuke; Taketa, Koji; Kimura, Shinichiro; Taguchi, Akihiro; Takayama, Kentaro; Yakushiji, Fumika; Hayashi, Yoshio
• Is Part Of: Asian journal of organic chemistry. Volume 4:Issue 10(2015:Oct.)
• Page Start: 1030
• Page End: 1033
• Publication Date: 2015-08-31
• Subjects: Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; 547.005
• DOI: 10.1002/ajoc.201500267
• Languages: English
• ISSNs: 2193-5807

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>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(<italic>t</italic>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.</p> </abstract>