Glycopeptide

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A glycopeptide, also called glycopeptide, is a peptide on which one or more glycosylations have been carried out.

biosynthesis

Due to glycosylation, glycopeptides have short chains of carbohydrates ( glycans ) that are bound to the peptide structure. Depending on the type of side chain involved in an amino acid, a distinction is made here between that on asparagine (in the case of an N- glycosylation through an amide bond ) and that on serine or threonine (in the case of an O -glycosylation through an ether bond ). In rare cases, a modification of tryptophan can also take place in the course of C -glycosylation .

Glycosylation is mostly a post-translational modification of proteins that were formed by translation on ribosomes during protein biosynthesis . On the other hand, some glycopeptides, for example in bacteria or fungi , are produced by a nonribosomal peptide synthesis .

synthesis

Synthetic (non-biochemical) methods for generating glycopeptides are e.g. B. solid phase synthesis and native chemical ligation as a form of protein ligation .

Purification

Depending on the type and extent of the glycosylation present, glycopeptides can be purified by affinity chromatography , e.g. B. with lectins .

use

One class of antibiotics belongs to the glycopeptides, the glycopeptide antibiotics such. B. Vancomycin , Teicoplanin , Telavancin , Ramoplanin and Decaplanin , as well as the chemotherapeutic agent Bleomycin .

Individual evidence

  1. ↑ T. de Beer, JF Vliegenthart, A. Löffler, J. Hofsteenge: The hexopyranosyl residue that is C-glycosidically linked to the side chain of tryptophan-7 in human RNase Us is alpha-mannopyranose. In: Biochemistry. Volume 34, Number 37, September 1995, pp. 11785-11789, PMID 7547911 .
  2. ↑ S. Ito, K. Hayama, J. Hirabayashi: Enrichment strategies for glycopeptides. In: Methods in molecular biology (Clifton, NJ). Volume 534, 2009, pp. 195-203, doi : 10.1007 / 978-1-59745-022-5_14 , PMID 19277551 .
  3. ↑ H. Tan, H. Guo, S. Wang, Q. Kong, W. Li, W. Zeng: Chemistry and biology of glycopeptides with antibiotic activity. In: Protein and peptide letters. Volume 21, Number 10, 2014, pp. 1031-1047, PMID 24975667 .