Teicoplanin aglycone | CAS#89139-42-4 | antibacterial glycopeptide

MedKoo Cat#: 461348 | Name: Teicoplanin aglycone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Teicoplanin aglycone is an antibacterial glycopeptide. It is antibiotic used in the prophylaxis and treatment of serious infections caused by Gram-positive bacteria, including methicillin-resistant Staphylococcus aureus and Enterococcus faecalis.

Chemical Structure

Teicoplanin aglycone

CAS#89139-42-4

Theoretical Analysis

MedKoo Cat#: 461348

Name: Teicoplanin aglycone

CAS#: 89139-42-4

Chemical Formula: C58H45Cl2N7O18

Exact Mass: 1197.2198

Molecular Weight: 1198.92

Elemental Analysis: C, 58.11; H, 3.78; Cl, 5.91; N, 8.18; O, 24.02

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

61036-62-2 (complex) 89139-42-4

Synonym

Teicoplanin aglycone; TD-A3;

IUPAC/Chemical Name

A name could not be generated for this structure.

InChi Key

DKVBOUDTNWVDEP-SUVRYANLSA-N

InChi Code

InChI=1S/C58H45Cl2N7O18/c59-32-9-21-1-7-38(32)84-41-16-26-17-42(51(41)74)85-39-8-4-24(14-33(39)60)50(73)49-57(80)66-48(58(81)82)31-19-28(69)20-37(72)43(31)30-13-23(3-5-35(30)70)45(54(77)67-49)64-56(79)47(26)65-55(78)46-25-11-27(68)18-29(12-25)83-40-15-22(2-6-36(40)71)44(61)53(76)62-34(10-21)52(75)63-46/h1-9,11-20,34,44-50,68-74H,10,61H2,(H,62,76)(H,63,75)(H,64,79)(H,65,78)(H,66,80)(H,67,77)(H,81,82)/t34-,44-,45+,46+,47-,48+,49+,50-/m1/s1

SMILES Code

Oc1cc(O)c2c([C@H](NC([C@H]3NC([C@H](c4cc2c(O)cc4)NC([C@H]5c6cc(Oc7ccc(C[C@@H]8C(N[C@H](C(N5)=O)c9cc(Oc%10cc([C@@H](N)C(N8)=O)ccc%10O)cc(O)c9)=O)cc7Cl)c(O)c(Oc%11c(Cl)cc([C@H]3O)cc%11)c6)=O)=O)=O)C(O)=O)c1

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.03.00

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,198.92 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Gonnella NC, Grinberg N, Mcloughlin M, Choudhary O, Fandrick K, Ma S. Three-dimensional structure of cyclic antibiotic teicoplanin aglycone using NMR distance and dihedral angle restraints in a DMSO solvation model. Magn Reson Chem. 2015 Oct;53(10):829-35. doi: 10.1002/mrc.4279. Epub 2015 Jul 1. PubMed PMID: 26138046. 2: Bick MJ, Banik JJ, Darst SA, Brady SF. Crystal structures of the glycopeptide sulfotransferase Teg12 in a complex with the teicoplanin aglycone. Biochemistry. 2010 May 18;49(19):4159-68. doi: 10.1021/bi100150v. PubMed PMID: 20361791; PubMed Central PMCID: PMC2888265. 3: Tollas S, Bereczki I, Sipos A, Rőth E, Batta G, Daróczi L, Kéki S, Ostorházi E, Rozgonyi F, Herczegh P. Nano-sized clusters of a teicoplanin ψ-aglycon-fullerene conjugate. Synthesis, antibacterial activity and aggregation studies. Eur J Med Chem. 2012 Aug;54:943-8. doi: 10.1016/j.ejmech.2012.06.054. Epub 2012 Jul 4. PubMed PMID: 22795664. 4: Ravichandran S, Collins JR, Singh N, W Wainer I. A molecular model of the enantioselective liquid chromatographic separation of (R,S)-ifosfamide and its N-dechloroethylated metabolites on a teicoplanin aglycon chiral stationary phase. J Chromatogr A. 2012 Dec 21;1269:218-25. doi: 10.1016/j.chroma.2012.08.019. Epub 2012 Aug 10. PubMed PMID: 22917979; PubMed Central PMCID: PMC3513553. 5: Schmid MG, Hölbling M, Schnedlitz N, Gübitz G. Enantioseparation of dipeptides and tripeptides by micro-HPLC comparing teicoplanin and teicoplanin aglycone as chiral selectors. J Biochem Biophys Methods. 2004 Oct 29;61(1-2):1-10. PubMed PMID: 15560917. 6: Malabarba A, Ferrari P, Cietto G, Pallanza R, Berti M. Synthesis and biological activity of N63-carboxypeptides of teicoplanin and teicoplanin aglycone. J Antibiot (Tokyo). 1989 Dec;42(12):1800-16. PubMed PMID: 2533594. 7: Xiao TL, Tesarova E, Anderson JL, Egger M, Armstrong DW. Evaluation and comparison of a methylated teicoplanin aglycone to teicoplanin aglycone and natural teicoplanin chiral stationary phases. J Sep Sci. 2006 Feb;29(3):429-45. PubMed PMID: 16544886. 8: Cavalleri B, Ferrari P, Malabarba A, Magni A, Pallanza R, Gallo GG. Teicoplanin, antibiotics from Actinoplanes teichomyceticus nov. sp. VIII. Opening of the polypeptide chain of teicoplanin aglycone under hydrolytic conditions. J Antibiot (Tokyo). 1987 Jan;40(1):49-59. PubMed PMID: 2951359. 9: Al-Majed AA. A direct HPLC method for the resolution and quantitation of the R-(-)- and S-(+)-enantiomers of vigabatrin (gamma-vinyl-GABA) in pharmaceutical dosage forms using teicoplanin aglycone chiral stationary phase. J Pharm Biomed Anal. 2009 Aug 15;50(1):96-9. doi: 10.1016/j.jpba.2009.03.030. Epub 2009 Apr 5. PubMed PMID: 19446423. 10: Printsevskaya SS, Reznikova MI, Korolev AM, Lapa GB, Olsufyeva EN, Preobrazhenskaya MN, Plattner JJ, Zhang YK. Synthesis and study of antibacterial activities of antibacterial glycopeptide antibiotics conjugated with benzoxaboroles. Future Med Chem. 2013 Apr;5(6):641-52. doi: 10.4155/fmc.13.16. PubMed PMID: 23617428. 11: Obeid S, Printsevskaya SS, Olsufyeva EN, Dallmeier K, Durantel D, Zoulim F, Preobrazhenskaya MN, Neyts J, Paeshuyse J. Inhibition of hepatitis C virus replication by semi-synthetic derivatives of glycopeptide antibiotics. J Antimicrob Chemother. 2011 Jun;66(6):1287-94. doi: 10.1093/jac/dkr104. Epub 2011 Mar 24. PubMed PMID: 21436155. 12: Schmid MG, Grobuschek N, Pessenhofer V, Klostius A, Gübitz G. Chiral resolution of diastereomeric di- and tripeptides on a teicoplanin aglycone phase by capillary electrochromatography. Electrophoresis. 2003 Aug;24(15):2543-9. PubMed PMID: 12900866. 13: Bechtold M, Felinger A, Held M, Panke S. Adsorption behavior of a teicoplanin aglycone bonded stationary phase under harsh overload conditions. J Chromatogr A. 2007 Jun 22;1154(1-2):277-86. Epub 2007 Mar 31. PubMed PMID: 17449046. 14: Fuereder M, Majeed IN, Panke S, Bechtold M. Model-based identification of optimal operating conditions for amino acid simulated moving bed enantioseparation using a macrocyclic glycopeptide stationary phase. J Chromatogr A. 2014 Jun 13;1346:34-42. doi: 10.1016/j.chroma.2014.03.056. Epub 2014 Apr 12. PubMed PMID: 24800971. 15: Steffeck RJ, Zelechonok Y. Enantioselective ion-exclusion chromatography on teicoplanin aglycone and (+)-(18-crown-6)-2,3,11,12-tetracarboxylic acid stationary phases. J Chromatogr A. 2003 Jan 3;983(1-2):91-100. PubMed PMID: 12568373. 16: Malabarba A, Ferrari P, Gallo GG, Kettenring J, Cavalleri B. Teicoplanin, antibiotics from Actinoplanes teichomyceticus nov. sp. VII. Preparation and NMR characteristics of the aglycone of teicoplanin. J Antibiot (Tokyo). 1986 Oct;39(10):1430-42. PubMed PMID: 2946651. 17: Bechtold M, Heinemann M, Panke S. Suitability of teicoplanin-aglycone bonded stationary phase for simulated moving bed enantioseparation of racemic amino acids employing composition-constrained eluents. J Chromatogr A. 2006 Apr 28;1113(1-2):167-76. Epub 2006 Feb 24. PubMed PMID: 16500665. 18: Bereczki I, Mándi A, Rőth E, Borbás A, Fizil Á, Komáromi I, Sipos A, Kurtán T, Batta G, Ostorházi E, Rozgonyi F, Vanderlinden E, Naesens L, Sztaricskai F, Herczegh P. A few atoms make the difference: synthetic, CD, NMR and computational studies on antiviral and antibacterial activities of glycopeptide antibiotic aglycon derivatives. Eur J Med Chem. 2015 Apr 13;94:73-86. doi: 10.1016/j.ejmech.2015.02.028. Epub 2015 Feb 20. PubMed PMID: 25752526. 19: Seneci P, Trani A, Ferrari P, Scotti R, Ciabatti R. Synthesis and biological activity of O56-substituted carboxyesters and carboxamides of teicoplanin aglycone. J Antibiot (Tokyo). 1992 Oct;45(10):1633-44. PubMed PMID: 1473991. 20: Borghi A, Ferrari P, Gallo GG, Zanol M, Zerilli LF, Lancini GC. Microbial de-mannosylation and mannosylation of teicoplanin derivatives. J Antibiot (Tokyo). 1991 Dec;44(12):1444-51. PubMed PMID: 1838104.