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US 9,175,006 B2Granted
Compositions and methods for cyclofructans as separation agents
AssigneeBoard of Regents, The University of Texas System
InventorsDaniel W. Armstrong, Ping Sun, Zachary S. Breitbach, Chunlei Wang
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Abstract
The present invention relates to derivatized cyclofructan compounds, compositions comprising derivatized cyclofructan compounds, and methods of using compositions comprising derivatized cyclofructan compounds for chromatographic separations of chemical species, including enantiomers. Said compositions may comprise a solid support and/or polymers comprising derivatized cyclofructan compounds.
Claims19
A chiral stationary phase comprising:
- a solid support;
- and
- a derivatized cyclofructan residue of formula I:
- wherein:
- n is 1-3;
- each L is, independently,
- O—C(═O), or
- O—C(═O)—NR2,
- each R is, independently,
- H,
- (C1-C20)alkyl optionally substituted with 1-3 R1,
- (C3-C20)cycloalkyl optionally substituted with 1-3 R1,
- (C5-C50)aryl optionally substituted with 1-3 R1,
- heteroaryl optionally substituted with 1-3 R1,
- (C1-C20)alkoxy(C 1 -C20)alkyl,
- H2C═CH— (when L is O—C(═0)),
- H2C═C(CH3)— (when L is O—C(═0)),
- alkylenyl-N═C═O;
- arylenyl-N═C═O;
- (C5-C50)aryl(C1-C20)alkyl optionally substituted with 1-3 R1, or
- saccharide residue lacking a hydroxyl group (when L is O), or
- comprises a covalent bond to said solid support;
- R1 is, independently, (C1-C10)alkyl optionally substituted with 1-3 R6, halo, hydroxy, —NR3R4, —COOR2, —COR2, nitro, trihaloalkyl, or —Si(OR2)3;
- R2 is, independently, H or (C1-C10)alkyl;
- R3 is, independently, H or (C1-C10)alkyl;
- R4 is, independently, H or (C1-C10)alkyl;
- R5 is, independently, (C1-C20)alkyl optionally substituted with 1-3 R1, (C5-C50)aryl optionally substituted with 1-3 R1, or heteroaryl optionally substituted with 1-3R1;
- R6 is, independently, halo, hydroxy, —NR3R4, —COOR2, —COR2, nitro, trihaloalkyl, or —Si(OR2)3;
- wherein one to five R groups comprise covalent bonds to the solid support;
- and
- wherein the average degree of derivatization ranges from about 2 to about 7.
28 more elements
A composition, comprising:
- a solid support;
- and
- at least one polymer, wherein said polymer comprises at least one residue of a derivatized cyclofructan of formula I:
- wherein:
- each n is, independently, 1-3;
- each L is, independently,
- O—C(═O), or
- O—C(═O)—NR2,
- each R is, independently,
- Y,
- Z,
- H,
- (C1-C20)alkyl optionally substituted with 1-3 R1,
- (C3-C20)cycloalkyl optionally substituted with 1-3 R1,
- (C5-C50)aryl optionally substituted with 1-3 R1,
- heteroaryl optionally substituted with 1-3 R1,
- (C1-C20)alkoxy(C1-C20)alkyl,
- H2C═CH— (when L is O—C(═0)),
- H2C═C(CH3)— (when L is O—C(═0)),
- alkylenyl-N═C═O;
- arylenyl-N═C═O;
- (C5-C50)aryl(C1-C20)alkyl optionally substituted with 1-3 R1, or
- saccharide residue lacking a hydroxyl group (when L is O),
- R1 is, independently, (C1-C10)alkyl optionally substituted with 1-3 R6, halo, hydroxy, —NR3R4, —COOR2, —COR2, nitro, trihaloalkyl, or —Si(OR2)3;
- R2 is, independently, H or (C1-C10)alkyl;
- R3 is, independently, H or (C1-C10)alkyl;
- R4 is, independently, H or (C1-C10)alkyl;
- R5 is, independently, (C1-C20)alkyl optionally substituted with 1-3 R1, (C5-C50)aryl optionally substituted with 1-3 R1, or heteroaryl optionally substituted with 1-3 R1;
- R6 is, independently, halo, hydroxy, —NR3R4, —COOR2, —COR2, nitro, trihaloalkyl, or —Si(OR2)3;
- and
- Y comprises a covalent bond to a different monomer residue;
- and
- Z comprises a covalent bond to said solid support;
- and
- wherein zero to five R groups comprise covalent bonds to the solid support;
- and
- wherein the average degree of derivatization ranges from about 2 to about 7.
34 more elements
A chiral stationary phase, comprising:
- a solid support;
- and
- a derivatized cyclofructan residue of formula I:
- wherein:
- n is 1-3;
- each L is, independently,
- O—C(═O) or O—C(═O)—NR2;
- each R is, independently, isopropyl, 3,5-dimethylphenyl, R-naphthylethyl carbamate, dichlorophenyl, cyclopentyl, cyclohexyl, and methylchlorophenyl;
- wherein one to five R groups comprise covalent bonds to the solid support;
- and
- wherein the average degree of derivatization ranges from about 2 to 24.
8 more elements
Dependencies are inferred from the claim text.