TEICOPLANIN

Teicoplanin A2-2: 34-O-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)-22,31-dichloro-7-demethyl- 64-O-demethyl-19-deoxy-56-O-(2-deoxy-2-((8-methyl-1-oxononyl)amino)-beta-D-glucopyranosyl)- 42-O- alpha-D-mannopyranosylristomycin A aglycone

Teicoplanin A2-3: 34-O-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)-22,31-dichloro-7-demethyl- 64-O-demethyl-19-deoxy-56-O-(2-deoxy-2-((1-oxodecyl)amino)-beta-D-glucopyranosyl)-42-O- alpha-D- mannopyranosylristomycin A aglycone

Teicoplanin A3-1: 34-O-(2-(Acetylamino)-2-deoxy-beta-D-glucopyranosyl)-22,31-dichloro-7- demethyl- 64-O-demethyl- 19-deoxy-42-O-alpha-D-mannopyranosylristomycin A aglycone

PRODUCT IDENTIFICATION

CAS RN

EINECS RN

FORMULA

MOLE WEIGHT

CLASSIFICATION

Antibiotic (Glycopeptide)

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

MELTING POINT

BOILING POINT

DENSITY

SOLUBILITY IN WATER

Freely soluble (sparingly soluble in N,N-dimethylformamide, insoluble in methanol, ethanol, acetonitrile, acetone, acetic acid, and in diethyl ether)

pH

6.3  - 7.3 (5% in water)

VAPOR DENSITY

REFRACTIVE INDEX

FLASH POINT

INCOMPATIBLE MATERIALS

Strong oxidizing agents

Carbon monoxide, Carbon dioxide, Nitrogen oxides. Hydrochloride

NFPA RATINGS

SAFETY

HAZARD NOTES

May cause slight blood, liver and kidney toxicity. May cause allergic reactions.

EYE

May cause eye irritation.

SKIN

May be harmful if absorbed through skin. May cause skin irritation.

INGESTION

May be harmful if swallowed.

INHALATION

May be harmful if inhaled. May cause respiratory tract irritation.

CHRONIC

TRANSPORT & REGULATORY INFORMATION

UN NO.

HAZARD SYMBOL

RISK PHRASES

SAFETY PHRASES

22-36/37-61

The glycopeptides vancomycin and teicoplanin are clinically important antibiotics. The carbohydrate portions of these molecules affect biological activity, and there is great interest in developing efficient strategies to make carbohydrate derivatives. To this end, genes encoding four glycosyltransferases, GtfB, C, D, E, were subcloned from Amycolatopsis orientalis strains that produce chloroeremomycin (GtfB, C) or vancomycin (GtfD, E) into Escherichia coli. After expression and purification, each glycosyltransferase (Gtf) was characterized for activity either with the aglycones (GtfB, E) or the glucosylated derivatives (GtfC, D) of vancomycin and teicoplanin. GtfB efficiently glucosylates vancomycin aglycone using UDP-glucose as the glycosyl donor to form desvancosaminyl-vancomycin (vancomycin pseudoaglycone), with kcat of 17 min-1, but has very low glucosylation activity, e 0.3 min-1, for an alternate substrate, teicoplanin aglycone. In contrast, GtfE is much more efficient at glucosylating both its natural substrate, vancomycin aglycone (kcat ) 60 min-1), and an unnatural substrate, teicoplanin aglycone (kcat ) 20 min-1). To test the addition of the 4-epi-vancosamine moiety by GtfC and GtfD, synthesis of UDP-β-L-4-epi-vancosamine was undertaken. This NDP-sugar served as a substrate for both GtfC and GtfD in the presence of vancomycin pseudoaglycone (GtfC and GtfD) or the glucosylated teicoplanin scaffold, 7 (GtfD). The GtfC product was the 4-epi-vancosaminyl form of vancomycin. Remarkably, GtfD was able to utilize both an unnatural acceptor, 7, and an unnatural nucleotide sugar donor, UDP- 4-epi-vancosamine, to synthesize a novel hybrid teicoplanin/vancomycin glycopeptide. These results establish the enzymatic activity of these four Gtfs, begin to probe substrate specificity, and illustrate how they can be utilized to make variant sugar forms of both the vancomycin and the teicoplanin class of glycopeptide antibiotics. (http://walsh.med.harvard.edu/)

Vancomycin is a member of the glycopeptide class of antibiotics. Vancomycin resistance (van) gene clusters are found in human pathogens such as Enterococcus faecalis, Enterococcus faecium and Staphylococcus aureus, glycopeptide-producing actinomycetes such as Amycolotopsis orientalis, Actinoplanes teichomyceticus and Streptomyces toyocaensis and the nonglycopeptide producing actinomycete Streptomyces coelicolor. Expression of the van genes is activated by the VanS/ VanR two-component system in response to extracellular glycopeptide antibiotic. Two major types of inducible vancomycin resistance are found in pathogenic bacteria; VanA strains are resistant to vancomycin itself and also to the lipidated glycopeptide teicoplanin, while VanB strains are resistant to vancomycin but sensitive to teicoplanin. Here we discuss the enzymes the van genes encode, the range of diff erent VanS/ VanR two-component systems, the biochemistry of VanS/ VanR, the nature of the eff ector ligand(s) recognised by VanS and the evolution of the van cluster. (http://www.jic.ac.uk/)

SALES SPECIFICATION

APPEARANCE

pass Test A,B,C

ASSAY

900μg/mg

6.3  - 7.3 (5% in water)

WATER

15.0% max

Methanol 0.5% max
Acetone: 1.0% max

ACTIVE PRINCIPLES

Teicoplanin A2 : 80.0% min
Teicoplanin A3 : 15.0% max
Other Teicoplanin: 5.0% max

0.73EU/mg max

PACKING

PRICE INFORMATION