Adamantoylated Biologically Active Small Peptides and Glycopeptides Structurally Related to the Bacterial Peptidoglycan View Full Text


Ontology type: schema:Chapter     


Chapter Info

DATE

2013

AUTHORS

Ruža Frkanec , Branka Vranešić , Srdjanka Tomić

ABSTRACT

A large number of novel synthetic compounds representing smaller parts of original peptidoglycan molecules have been synthesized and found to possess versatile biological activity, particularly immunomodulating properties. A series of compounds containing the adamantyl residues coupled to peptides and glycopeptides characteristic for bacterial peptidoglycan was described. The new adamantylpeptides and adamantylglycopeptides were prepared starting from N-protected racemic adamantylglycine and dipeptide L-Ala-D-isoglutamine. The adamantyl glycopeptides were obtained by coupling the adamantyltripeptides with alpha-D-mannose moiety through spacer molecule of fixed chirality. Since the starting material was D,L-(adamantyl-glycine) the condensation products with the dipeptide were mixtures of diastereoisomers. The obtained diastereoisomers were separated, characterized, and tested for immunostimulating activity. An HPLC method for purity testing was developed and adapted for the particular compounds. More... »

PAGES

91-106

References to SciGraph publications

  • 1988. Immunostimulation with peptidoglycan or its synthetic derivatives in PROGRESS IN DRUG RESEARCH / FORTSCHRITTE DER ARZNEIMITTELFORSCHUNG / PROGRÈS DES RECHERCHES PHARMACEUTIQUES
  • 1989. Recommendations for the Assessment of Adjuvants (Immunopotentiators) in IMMUNOLOGICAL ADJUVANTS AND VACCINES
  • Identifiers

    URI

    http://scigraph.springernature.com/pub.10.1007/978-1-62703-652-8_7

    DOI

    http://dx.doi.org/10.1007/978-1-62703-652-8_7

    DIMENSIONS

    https://app.dimensions.ai/details/publication/pub.1031353453

    PUBMED

    https://www.ncbi.nlm.nih.gov/pubmed/24014436


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