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Synopsis of Structural, Biosynthetic, and Chemical Aspects of Glycopeptide Antibiotics

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Glycopeptides and Glycoproteins

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 267))

Abstract

Glycopeptide antibiotics represent a very important group of natural products with regard to medicinal application as antibacterials and for cancer treatment. A characteristic for assignment as a glycopeptide antibiotic, next to antibiotic potential, is the modification of the peptide aglycon with various types of carbohydrates. According to this definition, vancomycin (including five subtypes), ramoplanin, bleomycin, mannopeptimycins and salmochelin belong to the family of glycopeptide antibiotics. In this article, an overview is given on the structural aspects, the biosynthesis and the mode of action of glycopeptide antibiotics. Structure–activity relationships of important functional groups contributing to enhanced antibiotic properties are highlighted. Finally, similarities with regard to structural features, the biosyntheses and the modes of actions are discussed. According to current knowledge, glycopeptide antibiotics mostly act as inhibitors of bacterial cell wall biosynthesis. It is to be expected that the actual list of glycopeptides will be continuously extended due to discoveries from ongoing screening programs.

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Abbreviations

ACP:

Acyl carrier protein

BLM:

Bleomycin

Chp:

3-Chloro-4-hydroxyphenylglycine

Dab:

2,4-Diaminobutyric acid

Dhb:

2,3-Dihydroxybenzoic acid

Dpg:

3,5-Dihydroxyphenylglycine

Dpr:

2,3-Diaminopropionic acid

FTICR:

Fourier transform ion cyclotron resonance

Hpg:

4-Hydroxyphenylglycine

Hty:

β-Hydroxytyrosine

Mephe:

β-Methylphenylalanine

MIC:

Minimum inhibitory concentration

MPM:

Mannopeptimycin

MRSA:

Methicillin-resistant Staphylococcus aureus

NRPS:

Non-ribosomal peptide synthetase

orf :

Open reading frame

PBA:

Pyrimidoblamic acid

PBP:

Penicillin binding protein

PKS:

Polyketide synthase

SAR:

Structure–activity relationship

VRE:

Vancomycin-resistant enterococci

VRSA:

Vancomycin-resistant Staphylococcus aureus

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Acknowledgments

This work was supported by a grant of the European Union (COMBIG-TOP, LSHG-CT-2003-503491), the Deutsche Forschungsgemeinschaft (DFG, SU 239/3-3) and by an Emmy-Noether-Fellowship for young investigators of the DFG (SU 239/2-2).

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  1. Institut für Chemie/FG Organische Chemie, Technische Universität Berlin, Straße des 17. Juni 124, 10623, Berlin, Germany

    Falko Wolter, Sebastian Schoof & Roderich D. Süssmuth

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  1. Falko Wolter
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  2. Sebastian Schoof
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  3. Roderich D. Süssmuth
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Correspondence to Roderich D. Süssmuth .

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Valentin Wittmann

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Wolter, F., Schoof, S., Süssmuth, R.D. (2006). Synopsis of Structural, Biosynthetic, and Chemical Aspects of Glycopeptide Antibiotics. In: Wittmann, V. (eds) Glycopeptides and Glycoproteins. Topics in Current Chemistry, vol 267. Springer, Berlin, Heidelberg. https://doi.org/10.1007/128_041

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