TY - JOUR
T1 - Amino acid bioconjugation via iClick reaction of an oxanorbornadiene-masked alkyne with a MnI(bpy)(CO)3-coordinated azide
AU - Henry, Lucas
AU - Schneider, Christoph
AU - Mützel, Benedict
AU - Simpson, Peter V.
AU - Nagel, Christoph
AU - Fucke, Katharina
AU - Schatzschneider, Ulrich
PY - 2014/10/23
Y1 - 2014/10/23
N2 - The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.
AB - The catalyst-free room temperature iClick reaction of an unsymmetrically 2,3-disubstituted oxanorbornadiene (OND) as a "masked" alkyne equivalent with [Mn(N3)(bpy(CH3,CH3))(CO)3] leads to isolation of a phenylalanine ester bioconjugate, in which the model amino acid is linked to the metal moiety via a N-2-coordinated triazolate formed in a cycloaddition-retro-Diels-Alder (crDA) reaction sequence, in a novel approach to bioorthogonal coupling reactions based on metal-centered reactivity.
KW - Amino acid bioconjugation
KW - oxanorbornadiene-masked alkyne
KW - MnI(bpy)(CO)3-coordinated azide
UR - https://pubs.rsc.org/en/content/articlelanding/2014/cc/c4cc07892f
U2 - 10.1039/c4cc07892f
DO - 10.1039/c4cc07892f
M3 - Article
SN - 1359-7345
VL - 50
SP - 15692
EP - 15695
JO - Chemical Communications
JF - Chemical Communications
IS - 99
ER -