Tyrosine specific sequential labeling of proteins.
We report (a) on the synthesis of a long-wavelength fluorescent coumarin containing an allyloxy acetate moiety, (b) the synthesis of two linkers containing an allyloxy acetate and an alkyne or azide function, respectively, and (c) the selective modification human serum albumin by a sequential method involving Pd(II) catalyzed modification of the phenolic side chain of tyrosine residues with an alkyne bearing linker and a subsequent azide-alkyne click reaction with an azide functionalized long-wavelength emitting coumarin dye. The method is likely to be applicable to various kinds of azido-modified fluorophores, and the Pd(II)-catalyzed modification of the tyrosines may also be used to introduce other kinds of tags. With these reagents, tyrosine specific modulation of proteins and peptides becomes possible either directly or in a sequential manner.
'Lendület' Laboratory of Chemical Biology, Research Centre for Natural Sciences, Institute of Organic Chemistry, Hungarian Academy of Sciences, Pusztaszeri út 59-67, H-1025 Budapest, Hungary.
Gergely B
GB
Cserép
András
A
Herner
Otto S
OS
Wolfbeis
Péter
P
Kele
D000480:Alkynes / Q000737:chemistry; D001386:Azides / Q000737:chemistry; D002384:Catalysis; D057930:Click Chemistry; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D010165:Palladium / Q000737:chemistry; D012709:Serum Albumin / Q000737:chemistry*; D014443:Tyrosine / Q000737:chemistry*
D000480:Alkynes; D001386:Azides; D003374:Coumarins; D005456:Fluorescent Dyes; D012709:Serum Albumin; D014443:Tyrosine; D010165:Palladium; C030123:coumarin
Bioorthogonal chemistry; Chemical reporter; Click chemistry; Sequential labeling; Tyrosine tagging