TY - JOUR
T1 - Fast and pH-Independent Elimination of trans-Cyclooctene by Using Aminoethyl-Functionalized Tetrazines
AU - Sarris, Alexi J.C.
AU - Hansen, Thomas
AU - de Geus, Mark A.R.
AU - Maurits, Elmer
AU - Doelman, Ward
AU - Overkleeft, Herman S.
AU - Codée, Jeroen D.C.
AU - Filippov, Dmitri V.
AU - van Kasteren, Sander I.
PY - 2018/12/5
Y1 - 2018/12/5
N2 - The inverse-electron-demand Diels–Alder/pyridazine elimination tandem reaction, in which the allylic substituent on trans-cyclooctene is eliminated following reaction with tetrazines, is gaining interest as a versatile bioorthogonal process. One potential shortcoming of such currently used reactions is their propensity to proceed faster and more efficiently at lower pH, a feature caused by the nature of the tetrazines used. Here, we present aminoethyl-substituted tetrazines as the first pH-independent reagents showing invariably fast elimination kinetics at all biologically relevant pH values.
AB - The inverse-electron-demand Diels–Alder/pyridazine elimination tandem reaction, in which the allylic substituent on trans-cyclooctene is eliminated following reaction with tetrazines, is gaining interest as a versatile bioorthogonal process. One potential shortcoming of such currently used reactions is their propensity to proceed faster and more efficiently at lower pH, a feature caused by the nature of the tetrazines used. Here, we present aminoethyl-substituted tetrazines as the first pH-independent reagents showing invariably fast elimination kinetics at all biologically relevant pH values.
KW - bioorthogonal chemistry
KW - Diels–Alder reactions
KW - elimination
KW - nitrogen heterocycles
KW - pH effects
UR - http://www.scopus.com/inward/record.url?scp=85056309246&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=85056309246&partnerID=8YFLogxK
U2 - 10.1002/chem.201803839
DO - 10.1002/chem.201803839
M3 - Article
C2 - 30184286
AN - SCOPUS:85056309246
SN - 0947-6539
VL - 24
SP - 18075
EP - 18081
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
IS - 68
ER -
