Compounds and compositions that have an asialoglycoprotein receptor (ASGPR) binding ligand bound to an extracellular protein binding ligand for the selective degradation of the target extracellular protein in vivo to treat disorders mediated by the extracellular protein are described.

The present invention provides a novel process for preparing an oligosaccharide C-glycoside derivative of formula I, comprising reacting a compound of formula II with compound of formula III in the presence of at least one primary or secondary amine and at least one additive [in the formulae, the substituents are as defined herein], and novel oligosaccharide C-glycoside derivatives that can be prepared using the process. ##STR00001##

There is provided with a compound. The compound is represented by formula or a salt thereof. R.sub.1 is an aliphatic hydrocarbon group having 10 to 26 carbon atoms.

There is provided with a compound. The compound is represented by formula or a salt thereof. R.sub.1 is an aliphatic hydrocarbon group having 10 to 26 carbon atoms.

There is provided with a compound. The compound is represented by formula or a salt thereof. R.sub.1 is an aliphatic hydrocarbon group having 10 to 26 carbon atoms.

There is provided with a compound. The compound is represented by formula or a salt thereof. R.sub.1 is an aliphatic hydrocarbon group having 10 to 26 carbon atoms.

A method for preparing an intermediate by a reduced glutathione-indicated amino acid Maillard reaction is provided. The method includes a two-stage reaction at an increased temperature. A reduced glutathione is added after different times of a low-temperature reaction, and a subsequent Maillard reaction is effectively inhibited on a basis wherein a substance is interacted with an intermediate degradation product to reduce a formation of colored substances. Comparing with a browning of Maillard products after a high-temperature stage, a reaction time with a best color inhibition effect is found to be the optimal preparation condition of the intermediate, and the intermediate is prepared in an aqueous medium at a low temperature under this optimal preparation condition. The method uses the water soluble reduced glutathione as a tracer to improve a tracing accuracy comparing to cysteine.

A method for preparing an intermediate by a reduced glutathione-indicated amino acid Maillard reaction is provided. The method includes a two-stage reaction at an increased temperature. A reduced glutathione is added after different times of a low-temperature reaction, and a subsequent Maillard reaction is effectively inhibited on a basis wherein a substance is interacted with an intermediate degradation product to reduce a formation of colored substances. Comparing with a browning of Maillard products after a high-temperature stage, a reaction time with a best color inhibition effect is found to be the optimal preparation condition of the intermediate, and the intermediate is prepared in an aqueous medium at a low temperature under this optimal preparation condition. The method uses the water soluble reduced glutathione as a tracer to improve a tracing accuracy comparing to cysteine.

Disclosed are processes for the production of composition comprising one or more fructose amino acids, said process comprising the steps of: (a) providing plant material derived from a botanical source selected from plants of the families Solanaceae, Compositae, (Asteraceae), Guttiferae, Umbelliferae, Papaveraceae, Vitidaceae or Acanthaceae; (b) extracting one or more fructose amino acid(s) from said plant material; and optionally (c) detecting the presence and/or measuring the amount of said fructose amino acid(s) in the extract of step (b).

Disclosed are processes for the production of composition comprising one or more fructose amino acids, said process comprising the steps of: (a) providing plant material derived from a botanical source selected from plants of the families Solanaceae, Compositae, (Asteraceae), Guttiferae, Umbelliferae, Papaveraceae, Vitidaceae or Acanthaceae; (b) extracting one or more fructose amino acid(s) from said plant material; and optionally (c) detecting the presence and/or measuring the amount of said fructose amino acid(s) in the extract of step (b).