Teicoplanin
Teicoplanin (teichomycin) is an antibiotic glycopeptide and is related to vancomycin but is produced by Actinoplanes teichmyceticus. Its antibiotic action involves the inhibition of peptidoglycan synthesis in the cell wall of gram-positive bacteria. The molecule is comprised of 5 major components joined by specific fatty acid moieties. Teicoplanin has 20 chiral centers and 4 fused rings and, like vancomycin has a complex structure that provides a wide range of polar, dispersive and potential ionic interactive sites. Like vancomycin, in chromatography, teicoplanin is a very effective chiral stationary phase. Tycoplanin can be bonded to silica to provide a stable, very selective, chiral bonded phase. It can be used very effectively in either the polar or reversed phase mode by the judicious selection of the appropriate mobile phase. The macrolytic glycopeptides are used extensively as stationary phases in chiral chromatography
Author: RPW Scott
Book:Liquid Chromatography
Section:HPLC Chiral-Stationary-Phases Macrocyclic-Glycopeptide
This material
can also be bonded to 5 mm silica gel
particles by multiple covalent linkages. Teicoplanin contains 20 chiral centers
surrounding four molecular 'pockets' or 'cavities'. Neighboring groups are
strongly polar and aromatic rings provide ready polarizability. The proposed
structure of Teicoplanin is shown in figure 51. This stationary phase is
claimed to be complementary to the Vancomycin phase and can be used with the
same types of mobile phase, one often providing chiral selectivity, when the
other does not. Teicoplanin can be used in a reversed phase mode using strongly
HPLC Chiral-Stationary-Phases Macrocyclic-Glycopeptide
Author: RPW Scott
Book:Liquid Chromatography
Section:HPLC Chiral-Stationary-Phases Macrocyclic-Glycopeptide
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The column
used was 25 cm long, 4.6 mm I.D., packed with Chirobiotic T. The mobile phase
was methanol containing acetic acid and triethylamine in the concentrations
shown in figure 52. The column was operated at room temperature and at a flow
rate of 2 ml/min. Teicoplanin is stable over a pH range of 3.8 to 6.5 although
it can be used for limited periods of time outside this range. By suitable
choice of mobile phase, Teicoplanin can be used in the reversed phase mode.
Another
macrolytic glycopeptide that has been used as a chiral stationary phase, is the
glycopeptide, Avoparcin [40]. This stationary phase is available as CHIROBIOTIC
A. Avoparcin is an antibiotic complex produced by Streptomysces candidus.
In particular, it is used to prevent
HPLC Chiral-Stationary-Phases Macrocyclic-Glycopeptide
Author: RPW Scott
Book:Liquid Chromatography
Section:HPLC Chiral-Stationary-Phases Macrocyclic-Glycopeptide
phase. Consequently,
the remaining dominant retentive forces will be polar or ionic. In the second
case, the mobile phase is predominantly water and thus provides strong polar
interactions with the solute but weak dispersive interactions. It also follows,
that the dispersive forces will dominate in the stationary phase. These two
examples demonstrate the useful flexibility of Vancomycin.
Another
macrolytic glycopeptide used in chiral chromatography is the amphoteric
glycopeptide Teicoplanin which is commercially available under the trade name
of CHIROBIOTIC T.
A, B, C and D are inclusion cavities. Molecular weight 1885. Chiral
centers 20, Sugar moieties 3, and R is CH3-decanoic acid
Courtesy of ASTEC Inc.
Figure 51.
The Proposed Structure of Teicoplanin
HPLC Chiral-Stationary-Phases Macrocyclic-Glycopeptide
Author: RPW Scott
Book:Preparative Chromatography
Section:Preparative Chlorokynurenine-Enantiomers
It also
contains two sugar moieties and has a molecular weight of 1449. This material
has multimodal capabilities, great stability and high chromatographic capacity
for preparative work. It is complimentary in chiral selectivity to the
antibiotics Teicoplanin and Ristocetin. An example of the use of Vancomycin in
preparative chromatography is demonstrated in the separation of the enantiomers
of Nicardipine. Nicardipine is a cerebral and coronary dilator with calcium
blocking activity. It chemical name is
1,4-dihydro2,6-dimethyl4-[3-nitrophenol]3,5-pyridine dicarboxylic
methyl2-[methyl (phenylmethyl)amino]ester. It exists in two isomeric forms the
(a) form M.Pt.168-173˚C and the (b) form M.Pt. 179-181˚C.
The
chromatographic
Preparative Chlorokynurenine-Enantiomers