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Adamantoylated biologically active small peptides and glycopeptides structurally related to the bacterial peptidoglycan (CROSBI ID 48813)

Prilog u knjizi | izvorni znanstveni rad

Frkanec, Ruža ; Vranešić, Branka ; Tomić, Srđanka Adamantoylated biologically active small peptides and glycopeptides structurally related to the bacterial peptidoglycan // Peptide modifications to increase metabolic stability and activity / Čudić, Predrag (ur.). New York (NY): Humana Press, 2013. str. 91-106

Podaci o odgovornosti

Frkanec, Ruža ; Vranešić, Branka ; Tomić, Srđanka

engleski

Adamantoylated biologically active small peptides and glycopeptides structurally related to the bacterial peptidoglycan

A large number of novel synthetic compounds representing smaller parts of original peptidoglycan molecules, has 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.

adamantane, mannose, adamantylglycine, peptidoglycan monomer, adamantyltripeptide, bacterial peptydoglycan, adjuvant

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Podaci o prilogu

91-106.

objavljeno

Podaci o knjizi

Peptide modifications to increase metabolic stability and activity

Čudić, Predrag

New York (NY): Humana Press

2013.

978-1-62703-651-1

Povezanost rada

Kemija, Temeljne medicinske znanosti

Poveznice