US 12,416,638 B2
Methods for labeling amine-containing compounds
Michael J. Kimzey, Oakland, CA (US); and Alexander Gyenes, San Francisco, CA (US)
Assigned to Agilent Technologies, Inc., Santa Clara, CA (US)
Filed by Agilent Technologies, Inc., Santa Clara, CA (US)
Filed on Apr. 5, 2021, as Appl. No. 17/222,741.
Application 17/222,741 is a continuation of application No. 15/575,355, granted, now 11,002,742, previously published as PCT/US2016/034706, filed on May 27, 2016.
Claims priority of provisional application 62/168,654, filed on May 29, 2015.
Prior Publication US 2021/0223253 A1, Jul. 22, 2021
Int. Cl. G01N 33/58 (2006.01); C07D 207/46 (2006.01); G01N 33/68 (2006.01)
CPC G01N 33/6809 (2013.01) [C07D 207/46 (2013.01); G01N 33/582 (2013.01); G01N 33/6848 (2013.01); G01N 2400/10 (2013.01); G01N 2458/00 (2013.01); Y10T 436/143333 (2015.01); Y10T 436/173845 (2015.01)] 19 Claims
 
1. A method for labeling and, optionally, analyzing, a N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, glycosylamine, or other amine-containing compound in a sample, said method comprising: (a) mixing said N-glycan, amine-containing amino acid, amine-containing peptide, amine-containing protein, glycosylamine, or other amine-containing compound in a solution with a labeling compound (“Activated Procaine”) with the structure

OG Complex Work Unit Chemistry
or a solvate or a salt of said labeling compound, thereby creating a labeling mixture, and
(b) conducting said labeling at a labeling temperature of between 10° C.±2° C. to 60° C.±2° C.,
thereby creating a labeled, fluorescent, mass spectrometry-active derivative of said N-glycan, of said amine-containing amino acid, of said amine-containing peptide, of said amine-containing protein, of said glycosylamine, or of said other amine-containing compound in said sample.