Chiral HPLC Columns

Cyclofructan-based Chiral and HILIC HPLC and SFC Columns

Cyclofructans are cyclic oligosaccharides and the newest class of chiral stationary phases for HPLC, SFC, and HILIC. Invented by Prof. Daniel W. Armstrong and introduced by AZYP, LLC, the LARIHC™ and FRULIC™ derivatized cyclofructan-based columns are now available through Supelco/Sigma-Aldrich.

As organic chemists develop new chemical entities, chromatography column manufacturers must keep pace by developing new CSPs with different enantioselectivities. Professor Daniel W. Armstrong has a long-standing and well-deserved reputation of creating novel chemistries and turning them in to commercially-viable scientific products. Beginning with the cyclodextrins (CYCLOBOND and CHIRALDEX), the macrocyclic glycopeptides (CHIROBIOTIC), ionic liquids for chromatography (SLB-ILS series) and mass spec (MALDI, ESI), the cyclofructans are his latest offering to the chromatography community [1].

We recommend adding the LARIHC (“chiral” spelled backwards) phases to your chiral HPLC and SFC column screening protocol, especially the alkyl-derivative LARIHC CF6-P which has proven to be particularly useful for primary amines, a class of compounds that have proven difficult to separate on most CSPs [2]. In addition, all LARIHC columns are broadly selective and can be used in all modes of HPLC as well as SFC. When compared to other HILIC columns, the FRULIC HILIC phases have shown increased efficiency and selectivity for polar, achiral, analytes [3,4].

LARIHC Columns
FRULIC Columns

For inquiries and ordering information, please contact Supelco_Quotes@sial.com.

Chiral: LARIHC Columns back to top

LARIHC CF6-P

This new chiral stationary phase (CSP) was developed as an alkyl derivatized cyclofructan 6 chiral stationary phase. It has demonstrated pronounced enantioselectivity toward all types of primary amines, such as amino alcohols, amino esters, and amino amides. Baseline separation was achieved for simple aliphatic racemic amines that contained no other functionality. Unlike all current crown ether chiral stationary phases, this new column works more effectively with organic solvents and supercritical fluids. It also appears to have great capabilities for preparative-scale separations. No other existing phase can efficiently separate primary amines as well as AZYP’s LARIHC CF6-P phase. A recent study showed that this phase alone can separate 93% of tested racemic primary amines [2]. Additionally, the LARIHC CF6-P phase is broadly selective for many neutral analytes in the normal phase.

Product Name Dimensions* AZYP Part No. List Price (USD)** Supelco Part No.
LARIHC CF6-P 25 cm x 4.6 mm I.D., 5 µm L1001 $1,800 custom
LARIHC CF6-P 15 cm x 4.6 mm I.D., 5 µm L1002 $1,600 custom
LARIHC CF6-P 5 cm x 4.6 mm I.D., 5 µm L1003 $800 custom
LARIHC CF6-P 25 cm x 2.1 mm I.D., 5 µm L1006 $1,700 custom
LARIHC CF6-P 15 cm x 2.1 mm I.D., 5 µm L1004 $1,500 custom
LARIHC CF6-P 5 cm x 2.1 mm I.D., 5 µm L1005 $700 custom
* 5 cm length columns are used as guard columns. Other dimensions, including preparative, are available. Please inquire.
** US list prices shown. For pricing in other countries, please contact your local Sigma-Aldrich Office.


Common Conditions for Chromatograms below
Column: LARIHC™ CF6-P, 25 cm x 4.6 mm I.D., 5 µm (AZYP Part No.L1001,
available from Supelco/Sigma-Aldrich as a custom item)
Det.: UV at 254 nm
Flow Rate: 1 mL/min
Inj.: 5µL
Mobile Phase:  methanol:acetonitrile:acetic acid:triethylamine, 70:30:0.3:0.2
Temp.: 20 °C
Sample: (see chromatogram)
 
1-Aminoindan Enantiomers on LARIHC™ CF6-P
Sample: 1-aminoindan, 0.3 mg/mL in ethanol
 
 
Octopamine Enantiomers on LARIHC™ CF6-P
Sample: Octopamine, 0.3 mg/mL in ethanol
 
 
Trans-1-Amino-2-indanol Enantiomers on LARIHC™ CF6-P
Sample: Trans-1-Amino-2-indanol, 0.3 mg/mL in ethanol
 


LARIHC CF6-M

This phase is currently not available. We recommend the LARIHC CF6-P.


LARIHC CF6-RN

This CSP utilizes R-naphthylethyl-functionalized cyclofructan 6 as the chiral selector. This new CSP shows excellent enantioselectivity toward various types of analytes, including acids, secondary and tertiary amines, alcohols, and many neutral compounds. Its covalent-bonded nature allows the use of all common organic solvents creating a wide range of compound types that can be separated. This phase can be operated in all three modes. However, better resolution was obtained in the normal phase mode (due to higher selectivity) allowing for the potential for preparative separations. This phase is an excellent choice for enantiomers that are not primary amines.

Product Name Dimensions* AZYP Part No. List Price (USD)** Supelco Part No.
LARIHC CF6-RN 25 cm x 4.6 mm I.D., 5 µm L3001 $1,800 custom
LARIHC CF6-RN 15 cm x 4.6 mm I.D., 5 µm L3002 $1,600 custom
LARIHC CF6-RN 5 cm x 4.6 mm I.D., 5 µm L3003 $800 custom
LARIHC CF6-RN 25 cm x 2.1 mm I.D., 5 µm L3006 $1,700 custom
LARIHC CF6-RN 15 cm x 2.1 mm I.D., 5 µm L3004 $1,500 custom
LARIHC CF6-RN 5 cm x 2.1 mm I.D., 5 µm L3005 $700 custom
* 5 cm length columns are used as guard columns. Other dimensions, including preparative, are available. Please inquire.
** US list prices shown. For pricing in other countries, please contact your local Sigma-Aldrich Office.


LARIHC CF7-DMP

This new CSP was developed by as a 3,5-dimethylphenyl functionalized cyclofructan 7. This column also provides chiral recognition toward a broad variety of compounds. This phase can be used in all three modes of operation, but like other aromatic derivatized columns, it works most effectively in the normal phase. The LARIHC CF7-DMP is the only commercialized cyclofructan 7 based column. Most importantly, the LARIHC CF7-DMP demonstrates complementary enantioselectivity when compared to the LARIHC CF-6-RN phase. Having both these novel chiral stationary phases at your use will greatly increase your ability to separate non-primary amine containing enantiomers.

Product Name Dimensions* AZYP Part No. List Price (USD)** Supelco Part No.
LARIHC CF7-DMP 25 cm x 4.6 mm I.D., 5 µm L4001 $1,800 custom
LARIHC CF7-DMP 15 cm x 4.6 mm I.D., 5 µm L4002 $1,600 custom
LARIHC CF7-DMP 5 cm x 4.6 mm I.D., 5 µm L4003 $800 custom
LARIHC CF7-DMP 25 cm x 2.1 mm I.D., 5 µm L4006 $1,700 custom
LARIHC CF7-DMP 15 cm x 2.1 mm I.D., 5 µm L4004 $1,500 custom
LARIHC CF7-DMP 5 cm x 2.1 mm I.D., 5 µm L4005 $700 custom
* 5 cm length columns are used as guard columns. Other dimensions, including preparative, are available. Please inquire.
** US list prices shown. For pricing in other countries, please contact your local Sigma-Aldrich Office.


HILIC: FRULIC Columns back to top

FRULIC-N

The FRULIC-N column was developed as a neutral high porosity poly-hydroxy based stationary phase. This novel HILIC stationary phase shows excellent separating capabilities for nucleic compounds, purine derivatives, and carbohydrates in the HILIC mode. When compared to all other commercial HILIC columns, more selective, efficient and faster separations were obtained resulting in overall better performance in the HILIC mode [3,4].

Product Name Dimensions* AZYP Part No. List Price (USD)** Supelco Part No.
FRULIC-N 25 cm x 4.6 mm I.D., 5 µm F1001 $1,000 custom
FRULIC-N 15 cm x 4.6 mm I.D., 5 µm F1002 $900 custom
FRULIC-N 5 cm x 4.6 mm I.D., 5 µm F1003 $500 custom
FRULIC-N 25 cm x 2.1 mm I.D., 5 µm F1006 $900 custom
FRULIC-N 15 cm x 2.1 mm I.D., 5 µm F1004 $800 custom
FRULIC-N 5 cm x 2.1 mm I.D., 5 µm F1005 $400 custom
* 5 cm length columns are used as guard columns. Other dimensions, including preparative, are available. Please inquire.
** US list prices shown. For pricing in other countries, please contact your local Sigma-Aldrich Office.


FRULIC-C

The FRULIC-C column has a charged stationary phase covalently attached to porous silica. The hydrophilic charged cyclofructan 6 functionality facilitates the column suitable for HILIC mode separations. The FRULIC-C column can be used to separate polar and hydrophilic compounds such as beta blockers, organic acids, purine and purine derivatives, nucleosides, sugars and sugar derivatives and vitamins. This HILIC phase is particularly beneficial in separating acidic compounds. Also, it often results in faster separations than the FRULIC-N phase.

Product Name Dimensions* AZYP Part No. List Price (USD)** Supelco Part No.
FRULIC-C 25 cm x 4.6 mm I.D., 5 µm F2001 $1,000 custom
FRULIC-C 15 cm x 4.6 mm I.D., 5 µm F2002 $900 custom
FRULIC-C 5 cm x 4.6 mm I.D., 5 µm F2003 $500 custom
FRULIC-C 25 cm x 2.1 mm I.D., 5 µm F2006 $900 custom
FRULIC-C 15 cm x 2.1 mm I.D., 5 µm F2004 $800 custom
FRULIC-C 5 cm x 2.1 mm I.D., 5 µm F2005 $400 custom
* 5 cm length columns are used as guard columns. Other dimensions, including preparative, are available. Please inquire.
** US list prices shown. For pricing in other countries, please contact your local Sigma-Aldrich Office.


References:

  1. Ping Sun, Chunlei Wang, Zachary S. Breitbach, Ying Zhang, and Daniel W. Armstrong. Development of New HPLC Chiral Stationary Phases Based on Native and Derivatized Cyclofructans. Anal. Chem. 2009, 81, 10215–10226.
  2. Ping Sun and Daniel W. Armstrong. Effective enantiomeric separations of racemic primary amines by the isopropyl carbamate-cyclofructan6 chiral stationary phase. Journal of Chromatography A, 2010, 1217, 4904–4918.
  3. Qiu et al. 2011. JCA. 1218(2). 270-279.
  4. Padivitage et al. 2013. Anal Bioanal Chem. 405(27). 8837-8848.