Naslov
Synthesis and biological activity of N-(tert-butyloxycarbonyl)-(adamant-2-yl)-D, L-glycyl-peptidoglycan monomer

Autori
Šporec, Vesna ; Ljevaković, Đurđica ; Halassy Špoljar, Beata ; Frkanec, Ruža ; Krstanović, Marina ; Vranešić, Branka ; Tomašić, Jelka ; Benedetti, Fabio

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
Journal of Peptide Science, Programme of 27th European Peptide Symposium, Sorrento, 31.08.- 06.09. 2002. / - , 2002

Skup
27th European Peptide Symposium

Mjesto i datum
Sorrento, Italija, 31.08.2002. - 06.09.2002

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Peptidoglycan monomer; (N-tert-butyloxycarbonyl)-(adamant-2-yl)-D; L-glycyl-residue

Sažetak
Peptidoglycan monomer (PGM, GlcpNAc-MurpNAc-L-Ala-D-isoGln-L-meso-A2pm(eNH2)-D-Ala-D-Ala)exhibits immunomodulating activity. The aim of this work was to prepare the new derivative of PGM containing (N-tert-butyloxycarbonyl)-(adamant-2-yl)-D, L-glycyl-residue and to investigate the structure-activity relationship. The novel adamantylacyl derivative of PGM was prepared by acylation of e-amino group of diaminopimelic acid with symmetrical anhydride of N-(tert-butyloxycarbonyl)-(adamant-2-yl)-D, L-glycyne. The anhydride was prepared utilizing (a) DCC and (b) EDC. The reaction of the PGM with anhydride (a) gave a mixture of two products N-(tert-butyloxycarbonyl)-D, L-(adamantan-2-yl)-glycyl-peptidoglycan monomer (product A) and [N-(tert-butyloxycarbonyl)-D, L-(adamantan-2-yl)-glycyl]2-peptidoglycan monomer (product B) that have different chromatographical mobilities. The reaction with anhydride (b) resulted in product A only. Products were isolated by gel filtration on Sephadex LH 20 and their structures were confirmed. Activity in relation to the structure of the product A was examined in the two different models: in vitro (the susceptibility of A to the N-acetylmuramyl-L-alanine amidase) and in vivo (immunomodulating activity was tested in an experimental model in mice, using ovalbumin as antigen [1]). Product A was a good substrate for N-acetylmuramyl-L-alanine amidase which cleaves it, yielding the disaccharide and the respective peptide. Immunostimulating activity of product A was compared with the activity of PGM and (adamant-1-yl)-acetyl-PGM. Product A didn't exhibit immunostimulating effect in applied experimental model.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti

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