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A facile preparation of functional cycloalkynes via an azide-to-cycloalkyne switching approach

Author:
Yoshida, Suguru, Kuribara, Tomoko, Ito, Harumi, Meguro, Tomohiro, Nishiyama, Yoshitake, KarakiPresent address: Laboratory of Medicinal Chemistry, School of Pharmacy, Kitasato University, 5-9-1 Shirokane, Minato-ku, Tokyo 108-8641, Japan., Fumika, Hatakeyama, Yasutomo, Koike, Yuka, Kii, Isao, Hosoya, Takamitsu
Source:
Chemical communications 2019 v.55 no.24 pp. 3556-3559
ISSN:
1364-548X
Subject:
alkynes, azides, chemical reactions, copper, moieties, proteins
Abstract:
A facile method for preparing various functional cycloalkynes, including proteins incorporated with a cycloalkyne moiety, from the corresponding azides is developed. Treatment of diynes bearing strained and terminal alkyne moieties with a copper salt enabled terminal alkyne-selective click conjugation with azides, whereas a more azidophilic strained alkyne moiety was transiently protected from the click reaction via complexation with copper.
Agid:
6332180