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Inverse electron‐demand Diels‐Alder (iEDDA) bioorthogonal conjugation of half‐sandwich transition metallocarbonyl entities to a model protein
Author(s) -
Jamroz Daria,
FischerDurand Nathalie,
Palusiak Marcin,
Wojtulewski Sławomir,
Jarzyński Szymon,
Stępniewska Marlena,
Salmain Michèle,
Rudolf Bogna
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5507
Subject(s) - norbornene , tetrazine , chemistry , bioorthogonal chemistry , cycloaddition , cyclopentadiene , adduct , maleimide , diels–alder reaction , polymer chemistry , organic chemistry , polymerization , click chemistry , polymer , catalysis
Novel transition metallocarbonyl complexes carrying a norbornene or an oxanorbornene group were synthesized by [4 + 2] cycloaddition between the organometallic maleimide dienophiles and cyclopentadiene or furan, respectively. The oxanorbornene adduct was obtained as a mixture of endo and exo isomers as confirmed by X‐ray diffraction and NMR spectroscopy. The (oxa)norbornene groups further provided convenient chemical reporters to carry out inverse electron demand Diels‐Alder (iEDDA) reactions with tetrazine derivatives. Detailed kinetic studies with a model tetrazine revealed that faster rates of reaction were determined with both isomers of the oxanorbornene complex with respect to the norbornene complexes. Eventually, incorporation of metallocarbonyl entities into bovine serum albumin equipped with tetrazine handles was achieved as shown by IR spectroscopy of the protein conjugates.