Selective fluorogenic derivatization of 3-nitrotyrosine and 3,4-dihydroxyphenylalanine in peptides: a method designed for quantitative proteomic analysis.
There is a need for the selective derivatization and enrichment of posttranslational protein modifications from tissue samples. This chapter describes a method for the selective derivatization of 3-nitrotyrosine (after reduction to 3-amino-tyrosine) and 3,4-dihydroxyphenylalanine with benzylamine derivatives to yield 6-amino- and 6-benzylamine-substituted benzoxazoles, which display characteristic fluorescence properties. The methodology can be expanded to other substituted benzylamines, which carry functional groups for affinity enrichment.
Sharov
Victor S
VS
Department of Pharmaceutical Chemistry, University of Kansas, Lawrence, KS, USA.
Dremina
Elena S
ES
Pennington
Justin
J
Killmer
Jacque
J
Asmus
Christopher
C
Thorson
Maria
M
Hong
Sung Jung
SJ
Li
Xiaobao
X
Stobaugh
John F
JF
Schöneich
Christian
C
D000818:Animals; D002851:Chromatography, High Pressure Liquid; D004295:Dihydroxyphenylalanine / Q000737:chemistry*; D005456:Fluorescent Dyes / Q000032:analysis / Q000138:chemical synthesis / Q000737:chemistry; D006801:Humans; D008956:Models, Chemical; D010455:Peptides / Q000032:analysis* / Q000737:chemistry*; D040901:Proteomics / Q000379:methods*; D013050:Spectrometry, Fluorescence; D053719:Tandem Mass Spectrometry; D014443:Tyrosine / Q000031:analogs & derivatives* / Q000737:chemistry
D005456:Fluorescent Dyes; D010455:Peptides; C002744:3-nitrotyrosine; D014443:Tyrosine; D004295:Dihydroxyphenylalanine