Naslov
Synthesis of novel adamantylacetyl derivative of peptidoglycan monomer - biological evaluation of immunomodulatory peptidoglycan monomer and respective derivatives with lipophilic substituents on amino group

Autori
Ljevaković, Đurđica ; Tomašić, Jelka ; Šporec, Vesna ; Halassy Špoljar, Beata ; Hanzl-Dujmović, Ivana

Izvornik
Bioorganic and medicinal chemistry (0968-0896) 8 (2000), 10; 2441-2449

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
peptidoglycan monomer; adamantyacetyl peptidoglycan monomer; adjuvant

Sažetak
Novel synthetic analogue of immunomodulatory peptidoglycan monomer 1 (PGM), (adamant-1-yl)-CH2CO-PGM (2) was prepared by acylation of ƒŐ-amino group of diaminopimelic acid with symmetrical (adamant-1-yl)-acetic acid anhydride in the presence of triethylamine. The product was isolated by gel filtration on Sephadex G-25, followed by ion exchange chromatography on SP-Sephadex C-25. The susceptibility of (adamant-1-yl)-CH2CO-PGM to hydrolysis with N-acetylmuramyl-L-alanine amidase was demonstrated, and the product of hydrolysis, (adamant-1-yl)-CH2CO-pentapeptide 3 was characterized. Both 2 and 3 are water soluble and non-pyrogenic compounds. Immunomodulatory activity of PGM, (adamant-1-yl)-CH2CO-PGM and structurally related derivative Boc-Tyr-PGM was compared in experiments in vivo, in mice, using ovalbumin (OVA) as an antigen. All three tested compounds exhibited comparable immunostimulating effects with respect to the induction of anti-OVA IgG.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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