description

Iris Biotech offers a variety of substituted 4,8-diazacyclononynes. The alkyne moiety within the ring has a unique bent structure and high reactivity toward cycloaddition reactions. The reactivity of an alkyne heavily depends on the electronic and steric characteristics of the substituents as well as structural strain. In comparison to nonbent acyclic alkynes, cyclononyne alkynes show remarkably high reactivity. Such strain-promoted azide-alkyne cycloadditions (SPAAC) using cycloalkynes have served for reliable molecular conjugation in a broad range of fields. The nitrogens are used as connection points for a variety of functional units. In comparison to cyclooctynes, DACNs possess high thermal and chemical stability along with comparable click reactivity.

references

Heteroatom-embedded Medium-Sized Cycloalkynes: Concise Synthesis, Structural Analysis, and Reactions; R. Ni, N. Mitsuda, T. Kashiwagi, K. Igawa, K. Tomooka; Angew. Chem. Int. Ed. 2015; 54(4): 1190-1194. https://doi.org/10.1002/anie.201409910.

Selective strain-promoted azide-alkyne cycloadditions through transient protection of bicyclo[6.1.0]nonynes with silver or gold; K. Adachi, T. Meguro, Y. Sakata, K. Igawa, K. Tomooka, T. Hosoya, S. Yoshida; Chem. Commun. 2020; 56: 9823-9826. https://doi.org/10.1039/d0cc04606j.

Thieme Chemistry Journals Awardees: Where Are They Now? One-Pot Synthesis of Versatile Buckle Units for Click Chemistry: 4,8-Diazacyclononynes (DACNs); K. Igawa, S. Aoyama, Y. Kawasaki, T. Kashiwagi, Y. Seto, R. Ni, N. Mitsuda, K. Tomooka; Synlett 2017; 28: 2110-2114. https://doi.org/10.1055/s-0036-1588839.