NDLI: Phenylisothiocyanate as a Multiple Chemical Dimension Reagent for the Relative Quantitation of Protein Nitrotyrosine

Content Provider	Springer Nature Link
Author	Haandel, Leon Killmer, Jacque Li, Xiobao Schöneich, Christian Stobaugh, John F.
Copyright Year	2008
Abstract	A highly selective sequential derivatization sequence has been developed for the transformation of 3-nitrotyrosine to a 2-anilino-benzoxazole derivative. This sequence can be applied to any ortho-nitrophenol, such as 3-nitrotyrosine or 3-nitrotyrosine residues present in proteins and/or peptides as a result of oxidative stress. The sequence involves a standard reduction of the nitro functional group to the corresponding amine using aqueous dithionite, followed by aqueous solution coupling with phenylisothiocyanate (PITC) and then eventual product formation by a photochemical mediated intramolecular cyclization of the intermediate thiourea. While this cyclization step has been effected numerous times by various reagents commonly used in synthetic organic chemistry, many requiring non-aqueous reaction media, the present transformation appears to the be first description this reaction using 350 nm light in aqueous media. The resulting overall transformation provides a specific mass shift signature of 116 amu when conducted with 1H5-PITC and 121 amu with 2H5-PITC, thus forming the basis of relative quantitation by MS detection. In preliminary experiments, relative quantitation was accomplished for the decapeptide angiotensin I that had been subjected to nitration.
Starting Page	507
Ending Page	516
Page Count	10
File Format	PDF
ISSN	00095893
Journal	Chromatographia
Volume Number	68
Issue Number	7-8
e-ISSN	16121112
Language	English
Publisher	Vieweg Verlag
Publisher Date	2008-08-27
Publisher Place	Wiesbaden
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Column liquid chromatography–mass spectrometry Nitrotyrosine derivatization Phenylisothiocyanate Benzoxazole formation Photocyclization MS relative quantitation Stable isotope derivatization Measurement Science, Instrumentation Plant Sciences Biochemistry Pharmacy Organic Chemistry Analytical Chemistry
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Analytical Chemistry Biochemistry Clinical Biochemistry

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