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Preparation and Properties of Glutathion Conjugates of 2, 4, 5, 6-Tetrachloro-1, 3-dicyanobenzene


Hameršak, Zdenko; Hollosi, Miklos; Kontrec, Darko; Ladešić, Branko; Majer, Zsuzsa; Šunjić, Vitomir
Preparation and Properties of Glutathion Conjugates of 2, 4, 5, 6-Tetrachloro-1, 3-dicyanobenzene // Tetrahedron, 51 (1995), 8; 2331-2338 (međunarodna recenzija, članak, znanstveni)


Naslov
Preparation and Properties of Glutathion Conjugates of 2, 4, 5, 6-Tetrachloro-1, 3-dicyanobenzene

Autori
Hameršak, Zdenko ; Hollosi, Miklos ; Kontrec, Darko ; Ladešić, Branko ; Majer, Zsuzsa ; Šunjić, Vitomir

Izvornik
Tetrahedron (0040-4039) 51 (1995), 8; 2331-2338

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

Ključne riječi
Glutathione; synthesis; CD-spectroscopy

Sažetak
Preparation and spectroscopic properties of 2, 5, 6-trichloro-4-(S-.f-L-glutamyI-Lcysteinyl- glycine)-l.3-dicyanobenzene (2), 2, 5-dichloro-4, 6-di-(S-'c-L-glutamyI-L-eysteinyl-glycine)- 13-dicyanobenzene (3), and 5-ehloro-2, 4, 6-tri(S-7-L-glutamyl-L-cysleinyl-glyeine)-13-dicyanobenzenc (4), gluthation conjugates of the general fungicide ehlorothalonil (2, 4, 5, 6-tetraehloro-l, 3- dieyano~nzene, l) are reported. Optimal conditions for preparation and chromatographic separation of the single conjugates are described. N'MR-spectroscopic data allowed unambiguous determination of regioselectivity of conjugation reaction of chlorothalonil with glutathione. UV Spectra of 2-4 revealed significant long-wavelength band shift and enhancement of intensity with increasing number of thioulkyl groups attaebed to the aromatic ring. The UV band assignement is based on the UV-VIS sl~eetra of the model compounds $-7. The far-UV CD speeca are dominated by the chiral contribution of the amide chromophores. In a trifluoroethanol/water (70:30) mixture the peplide backbone of conjugate 2 likely adopts an ordered (folded) conformation, whereas peptides 3 and 4 show no significant tendency for forming ordered structmes.

Izvorni jezik
Engleski

Znanstvena područja
Kemija



POVEZANOST RADA


Projekt / tema
108-1080057-0043 - Nacionalni model kliničke baze podataka u maksilofacijalnoj onkologiji (Mihajlo Virag, )

Ustanove
Institut "Ruđer Bošković", Zagreb,
Medicinski fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus