The present invention provides a method for labeling or detecting a protein with certain glycosyl groups. The methods are particularly useful for detecting cancer cells comprising the detected glycosyl groups. The present invention further provides labeling agents and detection agents, labeled proteins and mixtures, and kits and arrays thereof.

The present invention provides a method for labeling or detecting a protein with certain glycosyl groups. The methods are particularly useful for detecting cancer cells comprising the detected glycosyl groups. The present invention further provides labeling agents and detection agents, labeled proteins and mixtures, and kits and arrays thereof.

According to the present invention, a crystal of an alkali metal N-acetylneuraminate anhydrate, and a process for producing a crystal of an alkali metal N-acetylneuraminate anhydrate, comprising adding or adding dropwise a solvent selected from the group consisting of alcohols and ketones to an aqueous N-acetylneuraminic acid solution containing an alkali metal-containing compound and having a pH of 3.0 to 9.0 to precipitate a crystal of an alkali metal N-acetylneuraminate anhydrate, and collecting the crystal of an alkali metal N-acetylneuraminate anhydrate from the aqueous solution, can be provided.

According to the present invention, a crystal of an alkali metal N-acetylneuraminate anhydrate, and a process for producing a crystal of an alkali metal N-acetylneuraminate anhydrate, comprising adding or adding dropwise a solvent selected from the group consisting of alcohols and ketones to an aqueous N-acetylneuraminic acid solution containing an alkali metal-containing compound and having a pH of 3.0 to 9.0 to precipitate a crystal of an alkali metal N-acetylneuraminate anhydrate, and collecting the crystal of an alkali metal N-acetylneuraminate anhydrate from the aqueous solution, can be provided.

There are provided inter alia stable anti-cancer compounds and splice modulators and methods of synthesis and use thereof.

The invention relates to methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid (3APS) in a subject, preferably a human subject. The invention encompasses compound that will yield or generate 3APS, either in vitro or in vivo. Preferred compounds include amino acid prodrugs of 3APS for use, including but not limited to the prevention and treatment of Alzheimer's disease

The invention relates to methods, compounds, compositions and vehicles for delivering 3-amino-1-propanesulfonic acid (3APS) in a subject, preferably a human subject. The invention encompasses compound that will yield or generate 3APS, either in vitro or in vivo. Preferred compounds include amino acid prodrugs of 3APS for use, including but not limited to the prevention and treatment of Alzheimer's disease

Disclosed are C-glycoside amine derivatives of the formula:
R—CH.sub.2—C(CH.sub.3)—NH—R.sub.2
wherein R is a saccharide (e.g., as described in U.S. Pat. No. 8,314,219) and R.sub.2 is an acyl moiety derived from any ketone of the formula R.sub.3—C(O)—R.sub.3 wherein R.sub.3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. In addition, a method for making the C-glycoside amine derivatives involving (1) reacting a saccharide (e.g., glucose) C-glycoside ketone with a catalyst (e.g., Rh), about 10 to about 25 fold excess NH.sub.3, and an organic solvent (e.g., methanol) to form a saccharide C-glycoside amine, and (2) reacting said saccharide C-glycoside amine with a catalyst (e.g., Rh), an organic solvent (e.g., methanol), and an acyl moiety derived from any ketone of the formula R.sub.3—C(O)—R.sub.3 wherein R.sub.3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated to form said C-glycoside amine derivative.

Disclosed are C-glycoside amine derivatives of the formula:
R—CH.sub.2—C(CH.sub.3)—NH—R.sub.2
wherein R is a saccharide (e.g., as described in U.S. Pat. No. 8,314,219) and R.sub.2 is an acyl moiety derived from any ketone of the formula R.sub.3—C(O)—R.sub.3 wherein R.sub.3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated. In addition, a method for making the C-glycoside amine derivatives involving (1) reacting a saccharide (e.g., glucose) C-glycoside ketone with a catalyst (e.g., Rh), about 10 to about 25 fold excess NH.sub.3, and an organic solvent (e.g., methanol) to form a saccharide C-glycoside amine, and (2) reacting said saccharide C-glycoside amine with a catalyst (e.g., Rh), an organic solvent (e.g., methanol), and an acyl moiety derived from any ketone of the formula R.sub.3—C(O)—R.sub.3 wherein R.sub.3 is C1 to C22 straight or branched chain hydrocarbon which may be saturated or unsaturated to form said C-glycoside amine derivative.

Disclosed herein are substrates and/or inhibitors of endo-O-sulfatase 1 (Sulf-1). According to some embodiments, the substrates and/or inhibitors of Sulf-1 are compounds of formula (I) or (II), ##STR00001##
In formula (I) or (II), n is 2 or 3; X is methylene, O, or N; R.sub.1 is —SO.sub.3M, or —SO.sub.2NH.sub.2; R.sub.2 is C.sub.1-6 alkyl or C.sub.1-6 alkylamine; and M is a monovalent cation selected from the group consisting of lithium, sodium, potassium, and ammonium. Also encompasses herein are methods of identifying and treating a subject having or suspected of having osteoarthritis. The method includes steps of (a) mixing a urine sample of the subject with 4-methylumbelliferyl sulfate (4-MUS) and a Sulf-1 inhibitor of formula (I) or (II); (b) determining a fluorescence intensity of the mixture of the step (a); and (c) treating the subject with an analgesic, a non-steroidal anti-inflammatory drug (NSAID), or a corticosteroid when the determined fluorescence intensity of the step (b) is smaller than that of a control sample, which is a mixture of the urine sample and 4-MUS.