US2022412963A1PendingUtilityA1
Fluorescence tagging of glycans and other biomolecules through reductive amination for enhanced ms signals
Est. expiryJun 21, 2036(~9.9 yrs left)· nominal 20-yr term from priority
G01N 33/533C07D 215/48
72
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Claims
Abstract
Novel reagents comprising MS active, fluorescent compounds having an activated functionality for reaction with aldehydes and useful in labeling biomolecules such as glycans and methods of making the same are taught and described.
Claims
exact text as granted — not AI-modified1 - 16 . (canceled)
17 . A kit for assaying biomolecules comprising a labeling compound selected from
(a) a compound of Formula X,
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3 is
R 3a is selected from ester, amide, amine, oxygen, urea, carbamate, carbonate, sulfur, thiourea, thiocarbamate, alkyl or carbonyl;
R 3b is
y=0-12; z=1-12;
and salts or solvates thereof;
(b) a compound of XA,
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof;
(c) a compound of XB:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof;
(d) a compound of XC:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof;
(e) a compound of XD:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof;
(f) a compound of XE:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof;
(g) a compound of XE:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof; or
(h) a compound of XG:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
18 . The kit of claim 17 , further comprising one or more endoglycosidases.
19 . The kit of claim 18 , further comprising a buffer.
20 . The kit of claim 18 , further comprising one or more surfactants.
21 . The kit of claim 18 , further comprising one or more compounds that can perform a chemical release of a glycoprotein.
22 . The kit of claim 17 , further comprising a separation device.
23 . The kit of claim 22 , wherein the separation device is a solid phase extraction device.
24 . The kit of claim 22 , wherein the separation device is a centrifugal filtration device.
25 . The kit of claim 17 , wherein the labeling compound is a compound of Formula X,
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3 is
R 3a is selected from ester, amide, amine, oxygen, urea, carbamate, carbonate, sulfur, thiourea, thiocarbamate, alkyl or carbonyl;
R 3b is
y=0-12;
z=1-12;
and salts or solvates thereof.
26 . The kit of claim 17 , wherein the labeling compound is a compound of XA,
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
27 . The kit of claim 17 , wherein the labeling compound is a compound of XB:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
28 . The kit of claim 17 , wherein the labeling compound is a compound of XC:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
29 . The kit of claim 17 , wherein the labeling compound is a compound of XD:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
30 . The kit of claim 17 , wherein the labeling compound is a compound of XE:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
31 . The kit of claim 17 , wherein the labeling compound is a compound of XF:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.
32 . The kit of claim 17 , wherein the labeling compound is a compound of XC:
wherein R 1 is selected from hydrogen, halogen, lower alkyl, lower alkenyl, lower alkynyl, lower alkanoyl, lower haloalkyl, lower haloalkenyl, lower haloalkynyl, lower cycloalkyl, lower acyloxy, hydroxy, amino, lower alkylamino, amido, nitro, lower alkylthio, lower alkylsulfinyl, lower alkylsulfonyl, sulfonate, sulfonic acid, N 3 , SH, SCH 3 , C(O)CH 3 , CO 2 CH 3 and CO 2 H;
R 3b is
z=1-12;
and salts or solvates thereof.Join the waitlist — get patent alerts
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