Novel amphipathic molecule based on tandem malonate and use thereof
AssigneeIndustry-University Cooperation Foundation Hanyang University Erica Campus
InventorsPil Seok CHAE, Hazrat HUSSAIN
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Abstract
Provided are a newly developed tandem malonate-based amphipathic molecule, a method of preparing the same, and a method of extracting, solubilizing, stabilizing, crystallizing or analyzing a membrane protein using the same. In addition, the compound may be used to efficiently extract membrane proteins having various structures and characteristics from a cell membrane, compared to a conventional compound, to stably store the proteins in an aqueous solution for a long time, and may be used in functional and structural analysis thereof. The analysis of the structures and functions of the membrane proteins is one of the most attractive fields in current biology and chemistry, which are closely related to new drug development.
Claims19
A compound represented by the following Formula 1:
- where R1 and R2 are each independently a substituted or unsubstituted C3-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 aryl group or an organic group having a steroid backbone;
- each of X1 to X4 is a saccharide;
- each of Y1 and Y2 is CH2, O or S;
- and
- Z is CH2 or S.
A method of preparing a compound represented by the following Formula 1, comprising:
- 1) synthesizing tetramethyl pentane-1,1,5,5-tetracarboxylate by linking two dimethyl malonate molecules with an alkyl chain;
- 2) introducing an alkyl chain by performing an alkylation reaction on two α-carbons present in the product of step 1);
- 3) reducing four methyl carboxylate groups of the product of step 2) to alcohols;
- 4) introducing a protective group-attached saccharide by performing a glycosylation reaction on the product of step 3);
- and
- 5) performing a deprotection reaction on the product of step 4):
- where R1 and R2 are each independently a substituted or unsubstituted C3-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, or a substituted or unsubstituted C3-C30 aryl group;
- each of X1 to X4 is a saccharide;
- each of Y1 and Y2 is CH2;
- and
- Z is CH2.
A method of preparing a compound represented by the following Formula 1, comprising:
- 1) synthesizing thioether-containing tetraol by adding 5,5-bis-bromomethyl-2,2-dimethyl-[1,3]dioxane to a solution of 1-alkanol, dialkylated mono-ol, cholesterol, cholestanol or diosgenin;
- 2) introducing a protective group-attached saccharide by performing a glycosylation reaction on the product of step 1);
- and
- 3) performing a deprotection reaction on the product of step 2):
- where R1 and R2 are each independently a substituted or unsubstituted C3-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 aryl group or an organic group having a steroid backbone;
- each of X1 to X4 is a saccharide;
- each of Y1 and Y2 is O or S;
- and
- Z is S.
A method of extracting, solubilizing, stabilizing, crystallizing or analyzing a membrane protein, comprising:
- treating a membrane protein with a compound represented by the following Formula 1 in an aqueous solution:
- where R1 and R2 are each independently a substituted or unsubstituted C3-C30 alkyl group, a substituted or unsubstituted C3-C30 cycloalkyl group, a substituted or unsubstituted C3-C30 aryl group or an organic group having a steroid backbone;
- each of X1 to X4 is a saccharide;
- each of Y1 and Y2 is CH2, O or S;
- and
- Z is CH2 or S.
Dependencies are inferred from the claim text.