Amphipathic compound having novel penta-saccharide hydrophilic group and use thereof

A method of preparing a compound represented by Formula 1 below, the method comprising:

• preparing dialkylated diethylmalonate by adding a 1-iodoalkane to diethyl malonate;
• preparing a dialkylated mono-ol by adding LiCl, DMSO and H2O to the prepared dialkylated diethylmalonate, heating the mixture to a temperature of 150 to 200° C., and adding LiAlH4 and THF to the mixture;
• introducing a protecting group-attached glucose by performing a glycosylation reaction on the prepared dialkylated mono-ol;
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the introducing;
• attaching four glucose units with attached protecting groups by performing a glycosylation reaction on the product prepared in the removing to introduce a penta-saccharide hydrophilic group;
• and
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the attaching,
• wherein L represents a methylene group;
• A1 and A2 represent methylene groups;
• each of R1 and R2 independently represents a substituted or unsubstituted C3-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C3-C20 aryl group;
• Z represents a hydrogen atom;
• and X represents a glucose-centered branched penta-saccharide.

A method of preparing a compound represented by Formula 1 below, the method comprising:

• preparing an alcohol derivative by adding NaOH and an alcohol to epichlorohydrin;
• introducing a protecting group-attached glucose by performing a glycosylation reaction on the prepared alcohol derivative;
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the introducing;
• attaching four glucose units with attached protecting groups by performing a glycosylation reaction on the product prepared in the removing to introduce a penta-saccharide hydrophilic group:
• and
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the attaching,
• wherein L represents a direct bond;
• A1 and A2 represent oxygen atoms;
• each of R1 and R2 independently represents a substituted or unsubstituted C3-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C3-C20 aryl group;
• Z represents a hydrogen atom;
• and X represents a glucose-centered branched penta-saccharide.

A method of preparing a compound represented by Formula 1 below, comprising:

• preparing dialkylated diethylmalonate by adding a 1-iodoalkane to diethyl malonate;
• preparing a dialkylated diol by adding LiAlH4 and THF to the prepared dialkylated diethylmalonate;
• adding an alkyl chain by adding a 1-bromoalkane to the prepared dialkylated diol;
• introducing a protecting group-attached glucose by performing a glycosylation reaction on the product prepared in the adding;
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the introducing;
• attaching four glucose units with attached protecting groups by performing a glycosylation reaction on the product prepared in the removing to introduce a penta-saccharide hydrophilic group;
• and
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the attaching,
• wherein L represents a methylene group;
• Z represents —CH2-A3-R3, wherein one of A1 to A3 represents an oxygen atom and the others represent methylene groups;
• each of R1 to R3 independently represents a substituted or unsubstituted C3-C20 alkyl group;
• and R1 to R3 are the same;
• and X represents a glucose-centered branched penta-saccharide.

A method of preparing a compound represented by Formula 1 below, the method comprising:

• synthesizing a dialkylated diol using 5,5-bis-bromomethyl-2,2-dimethyl-[1,3]dioxane as a starting material;
• adding an alkyl chain by adding a 1-bromoalkane to the product prepared in the synthesizing;
• introducing a protecting group-attached glucose by performing a glycosylation reaction on the product prepared in the adding;
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the introducing;
• attaching four glucose units with attached protecting groups by performing a glycosylation reaction on the product prepared in the removing to introduce a penta-saccharide hydrophilic group;
• and
• removing an O-benzoyl group by performing a deprotection reaction on the product prepared in the attaching,
• wherein L represents a methylene group;
• Z represents —CH2-A3-R3, wherein A1 to A3 represent oxygen atoms;
• each of R1 to R3 independently represents a substituted or unsubstituted C3-C20 alkyl group;
• and R1 to R3 are the same;
• and X represents a glucose-centered branched penta-saccharide.

A method of extracting, solubilizing, stabilizing, crystallizing or analyzing membrane protein, the method comprising treating membrane proteins with a compound represented by Formula 1 below in an aqueous solution:

• wherein L represents a substituted or unsubstituted C1-C10 alkylene group, or a direct bond;
• each of A1 and A2 represents a methylene group or an oxygen atom;
• each of R1 and R2 independently represents a substituted or unsubstituted C3-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C3-C20 aryl group;
• X represents a glucose-centered branched penta-saccharide linked by oxygen;
• and
• Z represents a hydrogen atom or —CH2-A3-R3, wherein A3 represents a methylene group or an oxygen atom, and R3 independently represents a substituted or unsubstituted C3-C20 alkyl group, a substituted or unsubstituted C3-C20 cycloalkyl group, or a substituted or unsubstituted C3-C20 aryl group.