Rapid fluorescence tagging of glycans and other biomolecules with enhanced MS signals
Mass spectrometry (MS) active, fluorescent rapid tagging reagent is provided having three substituent groups: (a) a tertiary amino group or other MS active atom; (b) a highly fluorescent moiety; and (c) a reactive group that can react with an amine. The reactive group provides rapid tagging of desired bio-molecules. The fluorescent moiety provides the fluorescent signal. The tertiary amino group provides the MS signal.
1. A compound of the structural Formula IV-A:
or a salt or solvate thereof, wherein
X═C or N;
R 1 is independently selected from O═C═N—,
R 2 is independently selected from —H, —C 1 -C 8 alkyl, —C1-C 8 cycloalkyl, halo, dialkylamino, CH 2 -dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—; and
R 3 and R 4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, except that in the case where R 1 is O═C═N—, the requirement that either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid is removed.
2. A compound of claim 1 , wherein the structural formula is:
or a salt or solvate thereof, and X═C or N;
R 1 is independently selected from O═C═N—,
R 2 is independently selected from —H, —C 1 -C 8 alkyl, —C 1 -C 8 cycloalkyl, halo, dialkylamino, CH 2 -dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—; and
R 3 and R 4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein either R3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, except that in the case where R 1 is O═C═N—, the requirement that either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid is removed.
3. A compound of the structural Formula IV-B:
or a salt or solvate thereof, wherein
X═C or N;
R 1 is independently selected from O═C═N—,
R 2 is independently selected from —H, —C 1 -C 8 alkyl, —C1-C 8 cycloalkyl, halo, dialkylamino, CH 2 -dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—; and
R 3 and R 4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, except in the case where R 1 is O═C═N—, the requirement that either R3 or R4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid is removed.
4. A compound of the structural Formula VIII-A:
wherein
X═C or N;
R 1 is independently selected from O═C═N—,
R 2 is independently selected from —H, —C 1 -C 8 alkyl, —C 1 -C 8 cycloalkyl, halo, dialkylamino, CH 2 -dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—; and
R 3 and R 4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, except that in the case where R 1 is O═C═N—, the requirement that either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid is removed.
5. A compound of claim 4 , wherein the structural formula is:
and X═C or N;
R 1 is independently selected from O═C═N—,
R 2 is independently selected from —H, —C 1 -C 8 alkyl, —C 1 -C 8 cycloalkyl, halo, dialkylamino, CH 2 -dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—; and
R 3 and R 4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, except that in the case where R 1 is O═C═N—, the requirement that either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid is removed.
6. A compound of the structural Formula VIII-B:
wherein
X═C or N;
R 1 is independently selected from O═C═N—,
R 2 is independently selected from —H, —C 1 -C 8 alkyl, —C 1 -C 8 cycloalkyl, halo, dialkylamino, CH 2 -dialkylamino, aminocarbonyl, alkoxycarbonyl, or alkoxy, but not Cl or O═C═N—; and
R 3 and R 4 are independently selected from —H, alkyl, alkyl amino, alkylsulfonic acid, alkyl phosphonic acid, wherein either R 3 or R 4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid, except in the case where R 1 is O═C═N—, the requirement that either R3 or R4 is alkylamino, alkyl phosphonic acid, or alkylsulfonic acid is removed.
7. A compound of the formula: