Compound for labeling amine-containing compounds, and its use

1. A compound (“Activated Procaine”) with the structure

or a solvate or a salt of said compound.

2. A method for labeling, and optionally, analyzing, an N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound in a sample, said method comprising: reacting said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound with a labeling compound (“Activated Procaine”) with the structure

or a solvate or a salt of said labeling compound,

thereby creating a fluorescent, mass spectrometry-active derivative of said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound in said sample.

3. The method of claim 2 , wherein N-hydroxysuccinimide is present during said reacting of said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound with said Activated Procaine or solvate or salt thereof.

4. The method of claim 2 , wherein said fluorescent, mass spectrometry-active derivative of said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound is a fluorescent, mass spectrometry-active derivative of said N-glycan.

5. The method of claim 2 , wherein said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound amine-containing compound is an amine-containing peptide or amine-containing protein, which amine-containing peptide or amine-containing protein has an N-terminus and said reacting of said amine-containing peptide or amine-containing protein with said labeling compound occurs at said N-terminus.

6. The method of claim 2 , further comprising analyzing said fluorescent, mass spectrometry-active derivative of said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound by subjecting said fluorescent, mass spectrometry-active derivative of N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound to an analytical method.

7. The method of claim 6 , wherein said analytical method is selected from the group consisting of high-pressure liquid chromatography, capillary electrophoresis, fluorescence analysis, mass spectrometry, and a combination of any of these.

8. The method of claim 7 , wherein said combination is of fluorescence analysis and mass spectrometry.

9. A method for analyzing N-glycans, amine-containing amino acids, amine-containing peptides, amine-containing proteins, or other amine-containing compounds in a sample, comprising:

(i) contacting said N-glycans, amine-containing amino acids, amine-containing peptides, amine-containing proteins, or other amine-containing compounds in said sample with a labeling compound (“Activated Procaine”) with the structure

or a solvate or a salt of said labeling compound,

under conditions sufficient to create fluorescent, mass spectrometry-active derivatives of said N-glycans, of said amine-containing amino acids, of said amine-containing peptides, of said amine-containing proteins, or of said other amine-containing compounds in said sample,

(ii) subjecting said fluorescent, mass spectrometry-active derivatives of said N-glycans, of said amine-containing amino acids, of said amine-containing peptides, of said amine-containing proteins, or of said other amine-containing compounds to chromatographic methods, thereby separating said fluorescent, mass spectrometry-active derivatives of said N-glycans, of said amine-containing amino acids, of said amine-containing peptides, of said amine-containing proteins, or of said other amine-containing compounds, and

(iii) measuring fluorescence intensity of said separated fluorescent, mass spectroscopy-active derivatives of said N-glycans, of said amine-containing amino acids, said amine-containing peptides, of said amine-containing proteins, or of said other amine-containing compounds,

thereby analyzing said N-glycans, amine-containing amino acids, amine-containing peptides, amine-containing proteins, or other amine-containing compounds in said sample.

10. The method of claim 9 , wherein N-hydroxysuccinimide is present during step (i).

11. The method of claim 9 , further comprising step (iv):

(iv) subjecting said separated fluorescent, mass spectrometry-active derivatives of said N-glycans, amine-containing amino acids, amine-containing peptides, amine-containing proteins, or other amine-containing compounds to mass spectrometry to identify said separated fluorescent, mass spectrometry-active derivatives of said N-glycans, amine-containing amino acids, amine-containing peptides, amine-containing proteins, or other amine-containing compounds.

12. The method of claim 9 , wherein said amine-containing compounds are peptides or proteins each having an N-terminus containing a free amino group, which free amino group is labeled by said labeling compound at said amino group on said N-terminus.

13. A method of analyzing N-glycans present on a glycoprotein, said method comprising:

(i) releasing said N-glycans from said glycoprotein as glycosylamines, thereby obtaining released glycosylamines,

(ii) contacting said released glycosylamines with a labeling compound (“Activated Procaine”) with the structure

or a solvate or a salt of said labeling compound,

under conditions sufficient to create fluorescent, mass spectrometry-active derivatives of said released glycosylamines,

(iii) subjecting said fluorescent, mass spectrometry-active derivatives of said released glycosylamines to chromatography to obtain separated fluorescent, mass spectrometry-active derivatives of said released glycosylamines, and

(iv) measuring a fluorescent signal of said separated fluorescent, mass spectrometry-active derivatives of said released glycosylamines, thereby analyzing said N-glycans present on said glycoprotein.

14. The method of claim 13 , wherein N-hydroxysuccinimide is present during step (i).

15. The method of claim 13 , further comprising step (v):

(v), subjecting said separated released fluorescent, mass spectrometry-active derivatives of said glycosylamines to mass spectrometry to identify said fluorescent, mass spectrometry-active derivatives.

16. The method of claim 13 , wherein said releasing of said N-glycans from said glycoprotein in step (i) is by digestion of said glycoprotein with a deglycosylation enzyme.

17. The method of claim 16 , wherein said deglycosylation enzyme is PNGase F.

18. The method of claim 13 , wherein said glycoprotein is immobilized on a solid support.

19. The method of claim 18 , further comprising eluting said released glycosylamines away from said immobilized glycoprotein prior to step (ii).

20. A kit for labeling a compound of interest selected from the group consisting of an N-glycan, an amine-containing amino acid, an amine-containing peptide, an amine-containing protein, and another amine-containing compound in a sample, said kit comprising:

(i) a container,

(ii) a labeling compound, “Activated Procaine,” with the structure

or a solvate or a salt of said labeling compound, said labeling compound being disposed in said container, and

(iii) instructions for labeling said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, or other amine-containing compound with said labeling compound.

21. The kit of claim 20 , further comprising N-hydroxysuccinimide.

22. The kit of claim 20 , wherein said instructions are for labeling an N-glycan released from a glycoprotein or a glycopeptide as a glycosylamine.

23. The kit of claim 20 , further comprising an enzyme selected from the group consisting of an endoglycosidase, an exoglycosidase, and PNGase F.

24. The kit of claim 23 , wherein said enzyme is PNGase F.