# US 10,502,720 B2 · Methods for liquid chromatography calibration for rapid labeled N-glycans

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- Number: US 10,502,720 B2
- Document ID: US10502720B2
- Status: Granted
- Kind: B2
- Application number: 15/526,325
- Filed: 2015-11-12
- Published: 2017-11-23
- Granted: 2019-12-10
- Earliest claimed: 2014-11-13
- Assignees: Waters Technologies Corporation
- Applicants: Waters Technologies Corporation
- Inventors: Michael F. Morris; Matthew A. Lauber; Darryl W. Brousmiche
- Web page: https://patentgrep.com/patent/US10502720B2

## CPC

- G01N 30/02: Column chromatography
- B01D 15/305: {Hydrophilic interaction chromatography [HILIC]}
- C07D 215/48: Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07H 15/26: Acyclic or carbocyclic radicals, substituted by hetero rings
- G01N 30/04: Preparation or injection of sample to be analysed
- G01N 30/88: Integrated analysis systems specially adapted therefor, not covered by a single one of the groups G01N30/04 - G01N30/86
- G01N 33/6842: {Proteomic analysis of subsets of protein mixtures with reduced complexity, e.g. membrane proteins, phosphoproteins, organelle proteins}
- G01N 2030/027: {Liquid chromatography}
- G01N 2030/047: {external}
- G01N 2030/626: {calibration, baseline}
- G01N 2030/8836: {involving saccharides}
- G01N 2400/00: Assays, e.g. immunoassays or enzyme assays, involving carbohydrates
- G01N 2440/38: addition of carbohydrates, e.g. glycosylation, glycation
- G01N: INVESTIGATING OR ANALYSING MATERIALS BY DETERMINING THEIR CHEMICAL OR PHYSICAL PROPERTIES (measuring or testing apparatus or processes other than immunoassay, involving enzymes or microorganisms C12M, C12Q)
- B01D: SEPARATION (separating solids from solids by wet methods B03B, B03D; by pneumatic jigs or tables B03B; by other dry methods B07; magnetic or electrostatic separation of solid materials from solid materials or fluids, separation by high-voltage electric fields B03C; centrifuges, vortex apparatus B04; presses per se for squeezing-out liquid from liquid-containing material B30B9/02; treatment of water C02F, e.g. softening by ion-exchange C02F1/42; {arrangements of air intake cleaners in gas turbine plants F02C7/05} ; arrangements or mounting of filters in air-conditioning, air-humidification or ventilation F24F13/28)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C07H: SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS (derivatives of aldonic or saccharic acids C07C, C07D; aldonic acids, saccharic acids C07C59/105, C07C59/285; cyanohydrins C07C255/16; glycals C07D; compounds of unknown constitution C07G; polysaccharides, derivatives thereof C08B; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; sugar industry C13)

## Abstract

Methods are provided for making rapid labeled dextran ladders and other calibrants useful in liquid chromatography. The methodologies include a two-step process comprising a reductive amination step of providing a reducing glycan and reacting it with a compound having a primary amine to produce an intermediate compound. The intermediate compound is then rapidly tagged with a rapid tagging reagent to produce the rapid labeled dextran ladder.

## Claims

### Claim 1

A calibrant of the structural formula:
wherein R is a glucose unit or a monosaccharide unit.