Development of bis-unsaturated ester aldehydes as amino-glue probes: sequential double azaelectrocyclization as a promising strategy for bioconjugation.
The unsaturated ester aldehyde, (E)-3-alkoxycarbonyl-5-phenyl-2,4-dienal, was efficiently dimerized by applying the strain-promoted double-click reaction with sym-dibenzo-1,5-cyclooctadiene-3,7-diyne. The resulting dimerized probe was sequentially reacted first with one peptide molecule and then with a protein or the amino groups on the surface of a live cell through double azaelectrocyclization to achieve highly efficient bioconjugation.
RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako-shi, Saitama 351-0198, Japan. kotzenori@riken.jp.
Katsunori
K
Tanaka
Yuka
Y
Nakamoto
Eric R O
ER
Siwu
Ambara R
AR
Pradipta
Koji
K
Morimoto
Takeshi
T
Fujiwara
Suguru
S
Yoshida
Takamitsu
T
Hosoya
Yuki
Y
Tamura
Go
G
Hirai
Mikiko
M
Sodeoka
Koichi
K
Fukase
D000447:Aldehydes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry; D000818:Animals; D002470:Cell Survival; D003500:Cyclization; D019281:Dimerization; D004952:Esters; D006367:HeLa Cells; D006801:Humans; D051379:Mice; D010455:Peptides / Q000737:chemistry; D012709:Serum Albumin / Q000737:chemistry
D000447:Aldehydes; D000480:Alkynes; D004952:Esters; D010455:Peptides; D012709:Serum Albumin