US 11,747,310 B2
Methods for liquid chromatography calibration for rapid labeled N-glycans
Michael F. Morris, Ashland, MA (US); Matthew A. Lauber, North Smithfield, RI (US); and Darryl W. Brousmiche, Grafton, MA (US)
Assigned to Waters Technologies Corporation, Milford, MA (US)
Filed by WATERS TECHNOLOGIES CORPORATION, Milford, MA (US)
Filed on Oct. 25, 2019, as Appl. No. 16/664,403.
Application 16/664,403 is a continuation of application No. 15/526,325, granted, now 10,502,720, previously published as PCT/US2015/060326, filed on Nov. 12, 2015.
Claims priority of provisional application 62/079,460, filed on Nov. 13, 2014.
Prior Publication US 2020/0124574 A1, Apr. 23, 2020
Int. Cl. G01N 30/00 (2006.01); G01N 30/02 (2006.01); B01D 15/30 (2006.01); C07D 215/48 (2006.01); G01N 30/04 (2006.01); C07H 15/26 (2006.01); G01N 30/88 (2006.01); G01N 33/68 (2006.01); G01N 30/62 (2006.01)
CPC G01N 30/02 (2013.01) [B01D 15/305 (2013.01); C07D 215/48 (2013.01); C07H 15/26 (2013.01); G01N 30/04 (2013.01); G01N 30/88 (2013.01); G01N 33/6842 (2013.01); G01N 2030/027 (2013.01); G01N 2030/047 (2013.01); G01N 2030/626 (2013.01); G01N 2030/8836 (2013.01); G01N 2400/00 (2013.01); G01N 2440/38 (2013.01)] 1 Claim
OG exemplary drawing
 
1. A method of making a calibrant useful in liquid chromatography, comprising the steps of:
providing a reducing glycan having an aldehyde group;
reacting the aldehyde group of the reducing glycan with a compound having a primary amine through a reductive amination to produce an intermediary compound;
mixing the intermediary compound with a rapid tagging reagent, wherein the intermediary compound is rapidly labeled with the rapid tagging reagent; and
physically producing a rapid labeled dextran ladder having identical optical properties as a rapid labeled N-glycan wherein the rapid label N-glycan is produced by rapid tagging of a N-glycan with the rapid tagging reagent.