Astec CHIROBIOTIC

Macrocyclic Glycopeptide-Based Chiral

HPLC Phases

Columns for versatile,

robust chiral HPLC and
LC-MS separations
Aqueous and non-aqueous
separations on the same
column
No solvent or additive
memory effects
Wide applicability, especially
suited to polar and ionizable
compounds
Predictable scale-up from
analytical to prep
 Astec CHIROBIOTIC
Versatile Chiral HPLC and LC-MS Separations of Polar, Ionizable
and Neutral Compounds
Astec CHIROBIOTIC™ CSPs (chiral stationary phases) interact How do Astec CHIROBIOTIC CSPs separate
with polar, ionizable and neutral analytes via multiple molecular enantiomers?
interactions. This versatility means that the same Astec
Astec CHIROBIOTIC CSPs offer six different types of molecular
CHIROBIOTIC column can be successfully used in a variety of
interactions: ionic, H-bond,P-P, dipole, hydrophobic, and steric.
mobile phases, a significant benefit over CSPs that operate only in
They also possess multiple inclusion sites that influence selectivity
a single mode, normal or reversed-phase, for example, and must
based on the molecular shape of the analyte. The optimization
be dedicated to those mobile phase systems. However, the most
of enantiomer resolution is achieved by changing the mobile
interesting feature of Astec CHIROBIOTIC CSPs is the presence of
phase to leverage the types and relative strengths of the various
ionic interactions, which allows them to be used in polar ionic
interactions.
and reversed-phase modes for sensitive LC-MS operation.
What makes Astec CHIROBIOTIC CSPs unique?
Key application areas
The bonded macrocyclic glycopeptide itself (Figure 1), in terms
 Drug Discovery – High enantioselectivity, fast screening pro-
of its morphology, molecular composition, and multiple covalent
tocols, scalability to prep, reproducibility for reliable methods,
linkages to the silica surface, is what makes Astec CHIROBIOTIC
polar and non-polar analytes
CSPs unique and gives them significant and valuable benefits over
 Organic Synthesis – Compatible with all HPLC solvents to other CSPs. The truly differentiating feature of Astec CHIROBIOTIC
optimize sample solubility, fully scalable to prep CSPs is the presence of ionic interactions. These interactions are
 Bioanalytical, Drug Metabolism – High throughput, MS-com- unique to Astec CHIROBIOTIC CSPs and are responsible in large
patibility, aqueous samples, short run times, rugged columns part for their desirable retention characteristics toward polar and
ionizable analytes in aqueous and non-aqueous solvents.
Amino Acid and Peptide Analysis – Resolves underivatized
natural and synthetic chiral amino acids and peptides, differ- How do the Astec CHIROBIOTIC CSPs differ?
ent selectivity and higher preparative capacity than C18 for The various Astec CHIROBIOTIC phases share the benefits of
achiral amino acids robustness, flexibility in mobile phase options, ionic interactions,
compatibility with polar compounds and LC-MS, and preparative
What is the Astec CHIROBIOTIC family?
scalability. However, Astec CHIROBIOTIC CSPs differ in selectivity,
Developed originally by Advanced Separations Technologies primarily because of their differing number and types of
(Astec), the Astec CHIROBIOTIC family comprises highly interaction sites, and the number, type and accessibility of ionic
enantioselective CSPs based on macrocyclic glycopeptides that sites in the bonded macrocyclic glycopeptide.
have been bonded through multiple covalent linkages to high
purity silica particles. Astec CHIROBIOTIC CSPs offer flexibility in
choice of mobile phase conditions, both aqueous and non-
aqueous, and are ideal for analytical and preparative separations
of neutral, polar and ionic compounds.

The Astec CHIROBIOTIC CSP Family

Astec CHIROBIOTIC CSPs are based on 5, 10 or 16 μm, high-  Astec CHIROBIOTIC V and V2* – Vancomycin
purity, porous silica gel. They differ in the nature of the bonded  Astec CHIROBIOTIC T and T2* – Teicoplanin
macrocyclic glycopeptide and resulting enantioselectivity.
 Astec CHIROBIOTIC R – Ristocetin

*Astec CHIROBIOTIC V and T differ from V2 and T2, respectively, in their bonding  Astec CHIROBIOTIC TAG – Teicoplanin Aglycone
chemistry that gives them different selectivity and preparative capacity for certain
classes of analytes.

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Key features of Astec CHIROBIOTIC CSPs:  Solvent choices maximize sample solubility – Astec
 Aqueous and non-aqueous separations on the same column CHIROBIOTIC CSPs operate in highly-aqueous and non-
– Astec CHIROBIOTIC CSPs have H-bond, ionic, dispersive, aqueous polar mobile phases for polar compound solubility.
P-P, dipole stacking, steric, and inclusion mechanisms, usually They also operate in normal phase mobile phases to maximize
multiple types of interactions per analyte. solubility of non-polar compounds. Astec CHIROBIOTIC CSPs
are compatible with all organic solvents.
 Wide applicability – Applications cover a very broad range of
 Excellent preparative scalability and capacity –
compound classes, with the different Astec CHIROBIOTIC CSPs
showing complementary selectivity. From narrowbore to prep, separations on Astec CHIROBIOTIC
are fully scalable, even with polar analytes. By relying on pri-
 LC-MS compatibility – The wide choice of mobile phases marily aqueous eluents, the use and disposal of toxic organic
makes Astec CHIROBIOTIC CSPs ideal for LC-MS, where analyte solvents are eliminated. Additionally, preparative methods in
ionization and detection sensitivity are of critical concern. the non-aqueous polar ionic mode are just as easy to process
 No solvent or additive memory effect – The same Astec as normal phase solvents.
CHIROBIOTIC column can be used alternately in polar, reversed-  Fast kinetics for speed and efficiency – The kinetics of the
phase and normal phase solvents without damage, unlike cel- molecular interactions between the analyte and the Astec
lulosic and amylosic phases that require dedicated operation. CHIROBIOTIC CSP are fast, providing efficient separations and
 Robust columns with long lifetimes – Each macrocyclic glyco- relatively short retention times.
peptide molecule is linked to the silica surface via four or five  Orthogonal selectivity to other CSPs – The six Astec
covalent bonds for exceptional stability and long column life. CHIROBIOTIC CSPs are different from each other, and from
They are designed to withstand high pressure and flow rates, other types of CSPs to offer choices in enantioselectivity, like
as well as rapid changes in mobile phase conditions. reversal of elution order.

Figure 1. Proposed Structure of Vancomycin-based Astec CHIROBIOTIC V and V2

hydrogen bonding &

dipole stacking sites
ionic

C ionic

B
P-acceptor A

A, B, C are
inclusion sites
sugar
molecules

G004323

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 Incorporating Astec CHIROBIOTIC CSPs into Your
Chiral Column Screening Protocol
We recommend that you incorporate Astec CHIROBIOTIC into a single Astec CHIROBIOTIC column possesses multiple types
your routine screening protocol. Experience has shown that one of molecular interactions that are different in each of the four
or more of the Astec CHIROBIOTIC CSPs, particularly V2, T and distinct modes. The same column can be exposed to all of the
TAG, will perform the majority of chiral separations. Even if other conditions outlined in the screening protocol shown in Table 1
CSPs give adequate resolution, an Astec CHIROBIOTIC CSP may without any change or loss of performance. This versatility is just
allow use of mobile phases that are better suited to your sample one advantage that Astec CHIROBIOTIC CSPs have over other CSPs.
and detection method, or the Astec CHIROBIOTIC method may
The four Astec CHIROBIOTIC CSPs we recommend in the
be faster, more efficient, or more robust. An Astec CHIROBIOTIC
screening protocol are available in 25 cm or 10 cm column
method may also have advantages from a preparative standpoint
kits. Also, you can further expand the screening field by
in terms of solvent selection and sample capacity.
incorporating Astec CYCLOBOND™ bonded cyclodextrin and
For developing a new chiral HPLC method, we have created and Astec P-CAP™ chiral polymer CSPs into your screening protocol
use routinely in our laboratories a simple and rapid chiral column to accommodate other types of compounds not covered by the
screening protocol (Table 1). It is important to keep in mind that routine screen.

Table 1. The Astec CHIROBIOTIC Screening Protocol

columns: Astec CHIROBIOTIC V2, T, R, and TAG
procedure: Method development follows a simple strategy that tests polar ionic, polar organic, reversed-phase, and normal phase modes.

Separation Types of Screening Parameters

Mode Description Compound Mobile Phase to Optimize

Polar Ionic Polar organic solvents Acids, Bases, Zwitterions (100:0.1:0.1, v:v:v) Change acid-base ratio,
(CH3OH or CH3CN) CH3OH:Acetic Acid: change the type of acid or
containing small amounts Triethylamine base, add a volatile salt (test
of acid and base or salt different ammonium salts)
Reversed-Phase Typical RP eluents, water Acids, Bases, Zwitterions, (30:70) CH3CN:20mM Change the % and type of
or buffers with CH3OH Neutrals Ammonium Acetate, pH 4.0 organic modifier, adjust pH,
or CH3CN buffer type, and ionic strength
Polar Organic Polar organic solvents Neutrals 100% Ethanol Use other polar organic
without ionic additives solvents or blends
Normal Phase Non-polar organic solvents Neutrals (30:70) Ethanol:Heptane Increase % of polar modifier,
with polar solvent modifiers change both solvents

Method Optimization: Acid-Base Ratio, Temperature, and Flow Rate in Polar Ionic Mode
Using Astec CHIROBIOTIC CSPs in the polar ionic mode has The acid, base, or salt that is ultimately selected is based on its
the highest probability of success. Optimizing resolution compatibility, with the detection method (e.g. LC-MS), sample
usually involves changing the contribution to retention of ionic solubility, and whether the separation will be scaled up to
interactions between the analytes and functional groups in the preparative.
macrocyclic glycopeptide structure by:
 Changing the ratio of acid to base (Figure 2)
 Adding a soluble, volatile salt (instead of the acid and base)
directly to the methanol

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Figure 2. Demonstration of Polar Ionic Mode Mechanism: Effect of Acid:Base Ratio
Column CHIROBIOTIC V

Mobile Phase CH3OH/Acetic Acid/Triethylamine Mianserin

100/0.1/0.1 6.21

Acid:base ratio=1:1
7.36

G004324
G004327

100/0.15/0.05 10.44
Acid:base ratio=3:1

14.46 High acid: Nitrogen on mianserin is

positively charged, while -COOH group on
vancomycin is negatively charged: strong
G004325

ionic interaction

100/0.05/0.15 3.45 3.58

Acid:base ratio=1:3

High base: Nitrogen on mianserin group

is free amine, but -COOH group on
vancomycin is fully charged: weak ionic
G004326

interaction

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 Astec CHIROBIOTIC: Ideally Suited for LC-MS of
Polar, Ionizable and Neutral Compounds
Each of the various ionization sources has an optimal set of Typical polar ionic mobile phases are methanol with low
mobile phase conditions. Outside this set, ionization may be concentrations (0.1 – 0.001%) of volatile salts, like ammonium
suppressed with resulting loss in sensitivity. Astec CHIROBIOTIC acetate or ammonium formate. Figures 3 and 4 show examples
phases are uniquely able to operate across all mobile phase of Astec CHIROBIOTIC CSPs for LC-MS in reversed-phase and polar
systems. CSPs that are limited to normal phase operation, ionic mode mobile phases, respectively.
like many cellulosic and amylosic CSPs, reduce the options in In addition to mobile phase compatibility, the allowable high
detection methods. flow rates and short columns make them ideally suited to fast MS
ESI – Operate Astec CHIROBIOTIC CSPs in applications.
reversed-phase and unique Astec CHIROBIOTIC columns can be used in conjunction with
polar ionic modes. HybridSPE™-PPT plates to enhance sensitivity by completely
removing endogenous proteins and phospholipids. This approach
APCI – Operate Astec CHIROBIOTIC CSPs in was used to resolve the enantiomers of clenbuterol on an Astec
polar ionic mode. CHIROBIOTIC T column in Figure 4.
APPI – Operate Astec CHIROBIOTIC CSPs in
normal phase mode.

Figure 3. ESI-MS of Ketoprofen on Astec CHIROBIOTIC R in Reversed-phase Mode

column: Astec CHIROBIOTIC R, 15 cm x 2.1 mm, 5 μm particles (13019AST)
mobile phase: (30:70) CH3OH:20 mM ammonium acetate, pH 5.6
flow rate: 0.2 mL/min.
det.: ESI(-)
temp.: 35 °C 36
analyte: Ketoprofen

24
Ketoprofen
CPS

* 12

G004332
0

0 5 10
Min G004331

Figure 4. ESI-MS of Clenbuterol Extracted from Plasma on Astec CHIROBIOTIC T in Polar Ionic Mode
column: Astec CHIROBIOTIC T, 10 cm x 2.1 mm, 5 μm particles (12018AST)
mobile phase: 10 mM ammonium formate in CH3OH
flow rate: 0.3 mL/min. 700
det.: ESI(+)
temp.: 30 °C 600
analyte: Clenbuterol in rat plasma (10 ng/mL)
500

Clenbuterol 400 Clenbuterol

CPS

300
*
Phospholipids
200

100
G004333
0
0 1 2 3 4 5
Min G004245

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Unique Polar Ionic Mode
A valuable feature of Astec CHIROBIOTIC CSPs, the novel and example is shown in Figure 5. Additionally, compared to normal
very versatile polar ionic mode is popular because its mobile phase separations, the polar ionic mode has speed, efficiency, and
phases are polar organic solvents containing volatile additives sensitivity advantages, all valuable assets for LC-MS.
that are ideally suited for preparative and LC-MS applications. An

Figure 5. Beta-Receptors on Astec CHIROBIOTIC T in Polar Ionic Mode

column: Astec CHIROBIOTIC T, 25 cm x 4.6 mm, 5 μm particles (12024AST)
mobile phase: 15 mM ammonium formate in CH3OH
flow rate: 1 mL/min.
det.: UV at 220 nm
temp.: 25 °C
Clenbuterol

*
Clenbuterol

G004333
Metoprolol

Metoprolol
*
G004335
Sotalol Sotalol
Atenolol

*
G004334

Atenolol
*

0 12 24
G004336 Min G004337

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 Multi-modal Interactions Permit Use in
Aqueous and Non-aqueous Solvents
All Astec CHIROBIOTIC CSPs possess multiple interaction sites on Figure 6. Polar Ionic Mode
the same column. Changing the mobile phase affects the relative column: Astec CHIROBIOTIC V2, 25 cm x 4.6 mm, 5 μm particles
strength of specific types of interactions. The power and flexibility (15024AST)
mobile phase: 15 mM ammonium formate in CH3OH
of multi-modal Astec CHIROBIOTIC CSPs are demonstrated in flow rate: 1 mL/min.
Figures 6 through 10. The vancomycin-based Astec CHIROBIOTIC det.: UV at 230 nm
temp.: 25 °C Fluoxetine
CSPs were used successfully in four different modes.
analyte: Fluoxetine
Polar Ionic Mode
A valuable feature of Astec CHIROBIOTIC, the novel and very
versatile polar ionic mode mobile phase system is desirable
G004350
because of its high volatility and beneficial ionization effect for 8.47
LC-MS (Figure 6).
9.95
Reversed-phase Mode
Also highly suitable for LC-MS and polar analytes, reversed-
phase (RP) is a mode familiar to all chromatographers. Astec
CHIROBIOTIC CSPs have RP character and can be used in a wide
range of buffers and solvents (Figure 7).

Polar Organic Mode

Enantiomers of polar neutral analytes have been successfully
separated on Astec CHIROBIOTIC in the polar organic mode
where the mobile phase is typically a polar organic solvent or
solvent blend. Reaction mixtures, even in pyridine, can be run on
Astec CHIROBIOTIC in this mode (Figure 8). 0 7 14
Min G004351
Normal Phase Mode
Normal phase chiral separations are desirable to maintain
solubility of hydrophobic compounds and when analyzing Figure 7. Reversed-phase Mode
reaction mixtures in non-polar organic solvents. Astec column: Astec CHIROBIOTIC V, 25 cm x 4.6 mm, 5 μm particles
CHIROBIOTIC CSPs have the flexibility to operate in normal phase (11024AST)
mode. The same column can be used with normal phase and mobile phase: (30:70) CH3CN:5 mM ammonium acetate, pH 4.1
flow rate: 1 mL/min.
polar/aqueous solvents and additives without memory effects det.: UV at 254 nm Warfarin
(Figure 9). temp.: 25 °C
analyte: Warfarin

4.65 G004348

5.22

0 4 8
Min G004349

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Figure 8. Polar Organic Mode Figure 9. Normal Phase Mode
column: Astec CHIROBIOTIC V2, 25 cm x 4.6 mm, 5 μm particles column: Astec CHIROBIOTIC V, 25 cm x 4.6 mm, 5 μm particles
(15024AST) (11024AST)
mobile phase: CH3OH mobile phase: (95:5) hexane:ethanol
flow rate: 1 mL/min. flow rate: 1 mL/min.
det.: UV at 230 nm det.: UV at 205 nm
temp.: 25 °C temp.: 25 °C
analyte: Thalidomide analyte: Mephenytoin

1
Thalidomide Mephenytoin

G004346
G004344

0 7 14 0 10 20
Min G004347 Min G004345

Preparative Applications Using

Astec CHIROBIOTIC CSPs
 Scalability across all Astec CHIROBIOTIC particle sizes Preparative separations on Astec CHIROBIOTIC columns often

have speed and efficiency benefits over other CSPs. In terms of
Low retention times give high throughput
loading capacity, a 25 cm x 21.2 mm column has medium to high
Astec CHIROBIOTIC columns can be used in all preparative HPLC loadings, from a few mg to over 300 mg per injection.
techniques, including elution and recycle chromatography, mass-
Preparative separations on Astec CHIROBIOTIC are reproducible
directed prep, SFC, and simulated moving bed (SMB). Scale-up is
and scalable. Figure 10 shows the separation of phenylalanine
highly predictable because the same bonded phase chemistry is
isomers in reversed-phase mode on columns packed with 5, 10,
employed across all particle sizes. Multiple covalent bonds attach
and 16 μm particles of Astec CHIROBIOTIC T.
the Astec CHIROBIOTIC macrocyclic glycopeptides to the silica
surface, meaning no CSP ligand will contaminate the product.

Figure 10. Scalability Across Astec CHIROBIOTIC CSP Particle Sizes

column: Astec CHIROBIOTIC T, 25 cm x 4.6 mm
mobile phase: (50:50) ethanol:water
flow rate: 0.9 mL/min.
det.: UV at 220 nm

5.85 5.86 5.84

7.13
7.17
7.57

Min Min Min

5 μm 10 μm 16 μm
G004341 G004342 G004343

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 Figure 12. Sample Solubility Considerations in
Preparative Applications Preparative
(contd.) Analytical Scale
column: Astec CHIROBIOTIC V, 25 cm x 4.6 mm, 5 μm particles
A significant advantage of Astec CHIROBIOTIC for preparative (11024AST)
applications is the fact that the mobile phase can be chosen to mobile phase: CH3OH
optimize sample solubility – a critical preparative consideration. det.: UV at 293 nm
flow rate: 1 mL/min.
The examples here show preparative Astec CHIROBIOTIC analyte: Thalidomide
separations in three different mobile phase systems. 4.54

Preparative Reversed-phase and

Polar Ionic Modes
Preparative separations in reversed-phase and polar ionic mode
solvents have benefits over normal phase preparative separations
in terms of solvent safety and waste disposal costs. Figure
8.47
11 shows the use of Astec CHIROBIOTIC TAG in a preparative
separation in polar ionic mode.

Preparative Polar Organic Mode

Figure 12 shows the analytical and preparative separations of G004338
thalidomide enantiomers on Astec CHIROBIOTIC T. The analytical
scale gave an α value of 3.35 in 100% methanol and a retention Prep Scale
time under 10 minutes. However, since thalidomide is fairly
column: Astec CHIROBIOTIC V, 25 cm x 21.2 mm, 5 μm particles
insoluble in pure methanol, it was possible to add 20% dioxane (11044AST)
to the mobile phase to increase solubility 3.5-fold while still mobile phase: (80:20) CH3OH:dioxane
achieving the necessary separation. det.: UV at 313 nm
flow rate: 20 mL/min.
load: 70 mg in 12 mL
analyte: Thalidomide
4.15
4.79
Figure 11. Preparative Separation on Astec
CHIROBIOTIC TAG in Polar Ionic Mode
column: Astec CHIROBIOTIC TAG, 25 cm x 21.2 mm,
5 μm particles (14044AST)
mobile phase: 0.1% ammonium acetate in CH3OH
flow rate: 35 mL/min.
det.: UV at 300 nm
throughput: 20 mg/g CSP/hr.
load: 200 mg in 6 mL
analyte: N-Acetyl Tryptophan
2.86

4.53 G004339

Chiral Services: Column Screening and Small-

Scale Purification
Consult Supelco to obtain a quotation for our expert
services for chiral column screening (HPLC and GC), method
development and optimization, as well as isolation of up to 10
G004340
grams of purified enantiomer.
The complete listing of our chiral HPLC and GC columns can
be found at sigma-aldrich.com/chiral, our corporate chiral
web portal, where you can view our other products for chiral
chemistry, like chiral catalysts, building blocks, mobile phase
additives, derivatization reagents and more.

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Astec CHIROBIOTIC V and V2 Astec CHIROBIOTIC TAG
Bonded Macrocylic Bonded Macrocylic
Glycopeptide: Vancomycin Glycopeptide: Teicoplanin Aglycone
Chiral Centers: 18 Chiral Centers: 8
Sugar Moieties: 2 Sugar Moieties: 0
Inclusion Cavities: 3 Inclusion Cavities: 4
Separates a wide variety of secondary and tertiary amines in the The removal of the three sugar moieties enhances resolution of
polar ionic mode. Have many of the separation characteristics of many of the amino acids (alpha, beta, gamma, and cyclic). Astec
protein-based stationary phases but with exceptional stability and CHIROBIOTIC TAG has shown remarkable selectivity for sulfur-con-
much higher sample capacity. Astec CHIROBIOTIC V2 and V differ in taining molecules, such as sulfoxides and the amino acids methi-
the chemistry used to bond the glycopeptide to the silica, which onine, histidine, and cysteine. Neutral molecules, like oxazolidinones,
gives them differences in selectivity. hydantoins, and diazepines, have shown enhanced resolution and,
more remarkably, in single-solvent systems like methanol, ethanol,
Astec CHIROBIOTIC T and T2 and acetonitrile. Some acidic molecules have also shown increased
Bonded Macrocylic selectivity.
Glycopeptide: Teicoplanin
Chiral Centers: 23 Astec CHIROBIOTIC R
Sugar Moieties: 3 Bonded Macrocylic
Glycopeptide: Ristocetin A
Inclusion Cavities: 4
Chiral Centers: 38
These CSPs have resolved all of the known beta-blockers and
Sugar Moieties: 6
dihydrocoumarins and many other compound classes. Generally
reproduces chiral crown ether or ligand-exchange for amino acid Inclusion Cavities: 4
separations. Astec CHIROBIOTIC T2 and T differ in the chemistry used The presence of amines in the ristocetin structure makes it a good
to bond the glycopeptide to the silica, which gives them differences in choice when screening acidic compounds.
selectivity.

Astec CHIROBIOTIC Product Listing

For more information and to review our complete offering of Astec CHIROBIOTIC columns, please visit sigma-aldrich.com/chiral
Method Development Kits
ID (mm) Length (cm) Cat. No.

4.6 10 10300AST- One each of Astec CHIROBIOTIC V2, T, TAG and R

4.6 25 10305AST- One each of Astec CHIROBIOTIC V2, T, TAG and R

Astec CHIROBIOTIC Columns* V V2 T T2 TAG R

ID (mm) Length (cm) Cat. No. Cat. No. Cat. No. Cat. No. Cat. No. Cat. No.
5 μm
2.1 15 11019AST 15019AST 12019AST 16019AST 14019AST 13019AST
2.1 25 11020AST 15020AST 12020AST 16020AST 14020AST 13020AST
4.6 5 11021AST 15021AST 12021AST 16021AST 14021AST 13021AST
4.6 10 11022AST 15022AST 12022AST 16022AST 14022AST 13022AST
4.6 15 11023AST 15023AST 12023AST 16023AST 14023AST 13023AST
4.6 25 11024AST 15024AST 12024AST 16024AST 14024AST 13024AST
10 25 11034AST 15034AST 12034AST 16034AST 14034AST 13034AST
10 50 11036AST 15036AST 12036AST 16036AST 14036AST 13036AST
21.2 25 11044AST 15044AST 12044AST 16044AST 14044AST 13044AST
10 μm
4.6 25 11124AST 15124AST 12124AST 16124AST 14124AST 13124AST
*Other column dimensions, including guard columns and preparative dimensions, are found on our website or by inquiring to [email protected].

TRADEMARKS:
Astec CHIROBIOTIC, CYCLOBOND, HybridSPE, P-CAP – Sigma-Aldrich Biotechnology LP

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