Teicoplanin A2-2

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Teicoplanin A2-2
Category Antibiotics
Catalog number BBF-04445
CAS 91032-26-7
Molecular Weight 1879.66
Molecular Formula C88H97Cl2N9O33
Purity >98% by HPLC

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A major analogue of the family of lipoglycopeptide antibiotics produced by actinoplanes teichomyceticus. It possesses potent broad spectrum antibacterial activity against gram-positive bacteria, including MRSA and E. Faecalis.


Synonyms 34-O-[2-(acetylamino)-2-deoxy-β-D-glucopyranosyl]-22,31-dichloro-7-demethyl-64-O-demethyl-19-deoxy-56-O-[2-deoxy-2-[(8-methyl-1-oxononyl)amino]-β-D-glucopyranosyl]-42-O-α-D-mannopyranosyl-ristomycin A aglycone; MDL-507; Targocid; Teichomycin A2 factor 2; Teichomycin A2-2
Storage Store at -20°C under inert atmosphere
IUPAC Name (1S,2R,19R,22R,34S,37R,40R,52S)-2-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-22-amino-5,15-dichloro-64-[(2S,3R,4R,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-3-(8-methylnonanoylamino)oxan-2-yl]oxy-26,31,44,49-tetrahydroxy-21,35,38,54,56,59-hexaoxo-47-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-7,13,28-trioxa-20,36,39,53,55,58-hexazaundecacyclo[,6.214,17.219,34.18,12.123,27.129,33.141,45.010,37.046,51]hexahexaconta-3,5,8,10,12(64),14,16,23(61),24,26,29(60),30,32,41(57),42,44,46(51),47,49,62,65-henicosaene-52-carboxylic acid
Canonical SMILES CC(C)CCCCCCC(=O)NC1C(C(C(OC1OC2=C3C=C4C=C2OC5=C(C=C(C=C5)C(C6C(=O)NC(C7=C(C(=CC(=C7)O)OC8C(C(C(C(O8)CO)O)O)O)C9=C(C=CC(=C9)C(C(=O)N6)NC(=O)C4NC(=O)C1C2=CC(=CC(=C2)OC2=C(C=CC(=C2)C(C(=O)NC(CC2=CC(=C(O3)C=C2)Cl)C(=O)N1)N)O)O)O)C(=O)O)OC1C(C(C(C(O1)CO)O)O)NC(=O)C)Cl)CO)O)O
InChI InChI=1S/C88H97Cl2N9O33/c1-33(2)8-6-4-5-7-9-60(108)94-68-74(113)71(110)58(31-101)129-87(68)132-78-55-25-40-26-56(78)126-52-17-13-38(23-47(52)90)77(131-86-67(92-34(3)103)73(112)70(109)57(30-100)128-86)69-84(121)98-66(85(122)123)45-28-42(105)29-54(127-88-76(115)75(114)72(111)59(32-102)130-88)61(45)44-22-37(12-14-49(44)106)63(81(118)99-69)96-83(120)65(40)97-82(119)64-39-20-41(104)27-43(21-39)124-53-24-36(11-15-50(53)107)62(91)80(117)93-48(79(116)95-64)19-35-10-16-51(125-55)46(89)18-35/h10-18,20-29,33,48,57-59,62-77,86-88,100-102,104-107,109-115H,4-9,19,30-32,91H2,1-3H3,(H,92,103)(H,93,117)(H,94,108)(H,95,116)(H,96,120)(H,97,119)(H,98,121)(H,99,118)(H,122,123)/t48-,57-,58-,59-,62-,63-,64+,65-,66+,67-,68-,69+,70-,71-,72-,73-,74-,75+,76+,77-,86+,87+,88+/m1/s1
Source Actinoplanes sp.


Appearance White Solid
Antibiotic Activity Spectrum Gram-positive bacteria
Melting Point 250°C (dec.)
Density 1.68±0.1 g/cm3 (Predicted)
Solubility Soluble in Ethanol, Methanol, DMF, DMSO; Poorly soluble in Water

Reference Reading

1. Production of teicoplanin by valine analogue-resistant mutant strains of Actinoplanes teichomyceticus
Z H Jin, P L Cen, M R Wang Appl Microbiol Biotechnol . 2002 Jan;58(1):63-6. doi: 10.1007/s00253-001-0872-9.
Teicoplanin is a glycopeptide antibiotic produced by Actinoplanes teichomyceticus. A strain improvement to increase the productivity of the major component, teicoplanin A2-2, was carried out. As the fatty moiety of teicoplanin A2-2 is derived from L-valine, L-valine analogue (valine hydroxamate)-resistant mutants were derived. One of the mutants, 98-1-227, overproduced valine and produced a higher titer of total teicoplanin with higher A2-2 content. In a pilot fermentor (7 m3), the total productivity of teicoplanin was 1,800 units/ml and the A2-2 content was 58%.
2. Binding of teicoplanin to human serum albumin
A Assandri, A Bernareggi Eur J Clin Pharmacol . 1987;33(2):191-5. doi: 10.1007/BF00544566.
The interaction between the main components of the new glycopeptide antibiotic teicoplanin, A2-2, A2-3, A2-4, A2-5 and A3-1, and human serum albumin has been studied in vitro by equilibrium dialysis (pH 7.4, 37 degrees C). From Scatchard analysis of the data, the calculated association constants (Ka) were: A2-2, 2.47 X 10(4), A2-3, 2.86 X 10(4), A2-4, 2.95 X 10(4) and A2-5, 3.87 X 10(4) mol.l-1. The number of binding sites per albumin molecule ranged between 1.23 to 1.31. A3-1 had a lower affinity with a Ka of about 5 X 10(3) mol.l-1. Extrapolated to the in vivo situation, the data suggested that about 90-95% of A2 components will be bound to serum albumin, and about 68-72% of A3-1. The in vitro findings were confirmed by a pharmacokinetic study in volunteers given [14C] teicoplanin i.v., in whom the fraction of teicoplanin bound to serum protein ranged between 87.6 and 90.8%.
3. Quantification of teicoplanin in plasma by LC-MS with online sample clean-up and comparison with QMS assay
Daniel M Mueller, Arnold von Eckardstein, Lanja Saleh Clin Chem Lab Med . 2014 Jun;52(6):879-87. doi: 10.1515/cclm-2013-0974.
Background:Teicoplanin is a glycopeptide antibiotic used for the treatment of infections caused by Gram-positive bacteria. There is a good correlation between trough levels and clinical outcome, therefore therapeutic drug monitoring is recommended. Here we present a liquid chromatography-mass spectrometry (LC-MS) method with online extraction based on turbulent flow chromatography for the quantification of the five main components of teicoplanin, A2-1, A2-2, A2-3, A2-4, and A2-5.Methods:After online extraction, analytical chromatography was performed on a Hypersil Gold C8 column under acidic conditions. As mass spectrometer, a Q Exactive hybrid instrument was used. Samples were prepared by adding internal standard and subsequent centrifugation. Patient samples (n=125) that had previously been analyzed using a commercially available immunoassay (QMS teicoplanin) were re-analyzed by LC-MS.Results:The imprecision was <6.9%, inaccuracy between 99.6% and 109%, for both, within- and between-day analysis. The method was shown to be free of matrix effects in the relevant time ranges and was compared to a commercially available immunoassay, QMS® teicoplanin from Thermo Fisher Scientific. The LC-MS assay produced comparable results to the QMS assay, the correlation coefficient was 0.856 (95% confidence interval 0.800-0.896). LC-MS yielded lower concentrations than the immunoassay as could be demonstrated by the bias of -1.16 mg/L (95% confidence interval -1.90-0.43 mg/L) in the Bland-Altman analysis.Conclusions:This specific, automated, LC-MS assay for teicoplanin is suitable for therapeutic drug monitoring.

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