Chiral surfactants and methods for their use in chiral separations

A method for separating a chiral compound into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the general formula:
• ##STR7## wherein R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons;
• R.sub.2, R.sub.3 =H or C1-C8 linear or branched alkyl or alkenyl hydrocarbons;
• Y=CH.sub.2 ;
• A=NH;
• X=CO;
• C=carbon;
• Z=COO.sup.-, SO.sub.4.sup.-, SO.sub.3.sup.-, PO.sub.3.sup.-, PO.sub.4.sup.-, NR'.sub.3.sup.-, PR'.sub.3.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• and
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A method for separating a chiral compound into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the general formula:
• ##STR8## wherein R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having from one to five chiral centers, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons;
• Y=O, NH or CH.sub.2 ;
• A=NH, CO, SO or SO.sub.2 ;
• X=O or NH;
• C=a carbon atom;
• a.noteq.b, and n may be from 1 to 5;
• Z=COO.sup.-, SO.sub.4.sup.-, SO.sub.3.sup.-, PO.sub.3.sup.-, PO.sub.4.sup.-, NR'.sub.3.sup.-, PR'.sub.3.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• and
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A method for separating a chiral compound into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the following components:
• (1) a chiral selector, said chiral selector having at least one chiral center;
• (2) a hydrophilic head group bonded to said chiral selector;
• (3) a linker bonded to said chiral selector;
• and
• (4) a hydrophobic tail bonded to said linker,
• provided that said chiral surfactant is not an N-alkanoyl amino acidate;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A method for separating a hydrophilic chiral compound into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the general formula:
• ##STR9## wherein, R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons;
• Y=O, NH, or CH.sub.2 ;
• A=NH, CO, SO or SO.sub.2 ;
• X=CO, O or NH;
• C=carbon;
• a.noteq.b, and n may be from 1 to 5;
• Z=COO.sup.-, SO.sub.4.sup.-, SO.sub.3.sup.-, PO.sub.3.sup.-, PO.sub.4.sup.-, NR'.sub.3.sup.-, PR'.sub.3.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A method for separating a chiral compound having one or more acidic functional groups into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the general formula:
• ##STR10## wherein, R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons;
• Y=O, NH or CH.sub.2 ;
• A=NH, CO, SO or SO.sub.2 ;
• X=CO, O or NH;
• C=carbon;
• a.noteq.b, and n may be from 1 to 5;
• Z=NR'.sub.3.sup.-, PR'.sub.3.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A method for separating a chiral compound having one or more basic functional groups into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the general formula:
• ##STR11## wherein, R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons:
• Y=O, NH or CH.sub.2 ;
• A=NH, CO, SO or SO.sub.2 ;
• X=CO, O or NH;
• C=carbon;
• a.noteq.b, and n may be from 1 to 5;
• Z=COO.sup.-, SO.sub.4.sup.-, SO.sub.3.sup.-, PO.sub.3.sup.-, PO.sub.4.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A method for separating a zwitterionic chiral compound into its constituent enantiomers, comprising the steps of:

• (a) injecting said chiral compound into a channel that contains an electrolyte solution and a chiral surfactant that is present in the electrolyte solution in a concentration that is at or above its critical micelle concentration, said chiral surfactant having the general formula:
• ##STR12## wherein, R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons:
• Y=O, NH or CH.sub.2 ;
• A=NH, CO, SO or SO.sub.2 ;
• X=CO, O or NH;
• C=carbon;
• a.noteq.b, and n may be from 1 to 5;
• Z=COO.sup.-, SO.sub.4.sup.-, SO.sub.3, PO.sub.3.sup.-, PO.sub.4.sup.-, NR'.sub.3.sup.-, PR'.sub.3.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated;
• and
• (b) applying a voltage that causes migration of the chiral compound, thereby separating the constituent enantiomers of the chiral compound.

A chiral surfactant having the general formula:

• ##STR13## wherein, R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having from one to five chiral centers, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons;
• Y=O, NH or CH.sub.2 ;
• A=NH, CO, SO or SO.sub.2 ;
• X=O or NH;
• C=a carbon atom;
• a.noteq.b, and n may be from 1 to 5;
• Z=COO.sup.-, SO.sub.4.sup.-, SO.sub.3.sup.-, PO.sub.3.sup.-, PO.sub.4, NR'.sub.3.sup.-, PR'.sub.3.sup.-, OH, polyethers, zwitterions, or polyalcohols;
• and
• R'=H or C.sub.1 -C.sub.4 linear or branched hydrocarbon, optionally halogenated, optionally unsaturated.

A chiral surfactant having the general formula:

• wherein,
• R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons:
• C=carbon;
• n is an integer from 1 to 5;
• A=an amino acid side chain and b=H, or vice versa;
• and
• Z=OH or SO.sub.4.sup.-.

A chiral surfactant having the general formula:

• wherein,
• R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons:
• C=carbon;
• n is an integer from 1 to 5;
• A=an amino acid side chain and B=H, or vice versa;
• and
• Z=OH and SO.sub.4.sup.-.

A chiral surfactant having the general formula:

• wherein,
• R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons:
• C=carbon;
• n is an integer from 1 to 5;
• A=an amino acid side chain and B=H, or vice versa;
• and
• Z=OH and SO.sub.4.sup.-, or COO.sup.-.

A chiral surfactant having the general formula:

• wherein,
• R.sub.1 =C.sub.4 -C.sub.18 linear alkyls, C.sub.4 -C.sub.18 branched alkyls, C.sub.4 -C.sub.18 halogen-substituted linear alkyls, C.sub.4 -C.sub.18 polyether hydrocarbons, C.sub.4 -C.sub.18 alkyls having a chiral center, all alkyls optionally being unsaturated, and cholesterolic hydrocarbons:
• C=carbon;
• n is an integer from 1 to 5;
• A=an amino acid side chain and B=H, or vice versa;
• and
• Z=OH and SO.sub.4.sup.-.