Rapid fluorescence tagging of glycans and other biomolecules with enhanced ms signals
AssigneeWaters Technologies Corporation
InventorsDarryl W. Brousmiche, Ying-Qing Yu
Life of this patent
Estimating the term…
Abstract
Reagents comprising MS active, fluorescent molecules with an activated functionality for reaction with amines useful in tagging biomolecules such as N-glycans and uses thereof are taught and described.
Claims22
(canceled)
(canceled)
(canceled)
(canceled)
(canceled)
(canceled)
(canceled)
A compound of the structural formula:
A compound of the structural formula:
A compound of Formula IV:
- wherein
- X=C or N
- R1 is O═C═N— or
- R2 is independently selected from —H, —C1-C8 alkyl, —C1-C8 cycloalkyl, halo, dialkylamino, CH2-dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—;
- and
- R3 and R4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein R3 or R4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, and wherein R3 and R4 together with the nitrogen to which they are attached may form an optionally substituted 5- to 8-membered saturated or partially unsaturated ring but not when R1 is O═C═N—.
A compound of Formula V:
- wherein
- m=0-9;
- n=0-9;
- X=C or N
- R1 is O═C═N—, S═C═N—, or
- R2 is independently selected from methylene, substituted nitrogen, oxygen, carbonyl, amide, ester, sulfur, sulfoxide, or sulfone;
- R3 and R4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein R3 or R4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, and wherein R3 and R4 together with the nitrogen to which they are attached may form an optionally substituted 5- to 8-membered saturated or partially unsaturated ring;
- and
- R5 is independently selected from —H, —C1-C8 alkyl, —C1-C8 cycloalkyl, halo, dialkylamino, CH2-dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—, and not when R1 is S═C═N.
A method for analyzing a glycan, amino acid or other amine containing compound in a sample by means of liquid chromatography and mass spectrometry comprising labeling the glycan, amino acid or other amine containing compound in the sample by reacting with a compound of the structural formula:
- for a time and under conditions suitable to facilitate the labeling;
- providing a sample containing the glycan labeled with the compound;
- and subjecting the labeled compound to liquid chromatograph and mass spectrometry.
A method for analyzing a glycan, amino acid or other amine containing compound in a sample by means of liquid chromatography and mass spectrometry comprising labeling the glycan, amino acid or other amine containing compound in the sample by reacting with a compound of the structural formula:
- for a time and under conditions suitable to facilitate the labeling;
- providing a sample containing the glycan labeled with the compound;
- and subjecting the labeled compound to liquid chromatograph and mass spectrometry.
A method for analyzing a glycan, amino acid or other amine containing compound in a sample by means of liquid chromatography and mass spectrometry comprising labeling the glycan, amino acid or other amine containing compound in the sample by reacting with a compound of the structural formula
- for a time and under conditions suitable to facilitate the labeling;
- providing a sample containing the glycan labeled with the compound;
- and subjecting the labeled compound to liquid chromatograph and mass spectrometry.
A method for rapid tagging of a glycan, amino acid or other amine containing compound comprising the step of reacting a glycan, amino acid or other amine containing compound with the compound of the structural formula:
A method for rapid tagging of a glycan, amino acid or other amine containing compound comprising the step of reacting a glycan, amino acid or other amine containing compound with the compound of the structural formula:
A method for rapid tagging of a glycan, amino acid or other amine containing compound comprising the step of reacting a glycan, amino acid or other amine containing compound with the compound of the structural formula:
A method for rapid tagging of a glycan, amino acid or other amine containing compound comprising the step of reacting a glycan, amino acid, or other amine containing compound with a compound comprising:
- a tertiary amino group or other MS active atom;
- a highly fluorescent moiety;
- and
- a functional group that rapidly reacts with an amine.
Dependencies are inferred from the claim text.