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


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: Humana Press, 2013. str. 91-106


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

Autori
Frkanec, Ruža ; Vranešić, Branka ; Tomić, Srđanka

Vrsta, podvrsta i kategorija rada
Poglavlja u knjigama, znanstveni

Knjiga
Peptide modifications to increase metabolic stability and activity

Urednik/ci
Čudić, Predrag

Izdavač
Humana Press

Grad
New York

Godina
2013

Raspon stranica
91-106

ISBN
978-1-62703-651-1

Ključne riječi
Adamantane, mannose, adamantylglycine, peptidoglycan monomer, adamantyltripeptide, bacterial peptydoglycan, adjuvant

Sažetak
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.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
021-0212432-2431 - Nove formulacije antigena i imunostimulatora - utjecaj na imunoreakciju (Ruža Frkanec, )
119-1191344-3121 - Sinteze i enzimske transformacije biološki aktivnih spojeva (Srđanka Tomić-Pisarović, )

Ustanove
Imunološki zavod d.d.,
Prirodoslovno-matematički fakultet, Zagreb