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Pregled bibliografske jedinice broj: 234061

Synthesis, Structural Studies and Cytostatic Evaluation of 5, 6-di-O-Modified L-Ascorbic Acid Derivatives


Gazivoda, Tatjana; Wittine, Karlo; Lovrić, Iva; Makuc, Damjan; Plavec, Janez; Cetina, Mario; Mrvoš-Sermek, Draginja; Šuman, Lidija; Kralj, Marijeta; Pavelić, Krešimir et al.
Synthesis, Structural Studies and Cytostatic Evaluation of 5, 6-di-O-Modified L-Ascorbic Acid Derivatives // Carbohydrate research, 341 (2006), 4; 433-442 doi:10.1016/j.carres.2005.12.010 (međunarodna recenzija, članak, znanstveni)


Naslov
Synthesis, Structural Studies and Cytostatic Evaluation of 5, 6-di-O-Modified L-Ascorbic Acid Derivatives

Autori
Gazivoda, Tatjana ; Wittine, Karlo ; Lovrić, Iva ; Makuc, Damjan ; Plavec, Janez ; Cetina, Mario ; Mrvoš-Sermek, Draginja ; Šuman, Lidija ; Kralj, Marijeta ; Pavelić, Krešimir ; Mintas, Mladen ; Raić-Malić, Silvana

Izvornik
Carbohydrate research (0008-6215) 341 (2006), 4; 433-442

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

Ključne riječi
L-Ascorbic acid; configurational analysis; conformational analysis; single crystal X-ray diffraction; cytostatic activity

Sažetak
The 5, 6-di-O-tosylated derivative of L-ascorbic acid was synthesized by selective protection and deprotection of 2, 3- and 5, 6-dihydroxy functional groups involving 5, 6-ditosylation in the final step, while the novel 6-acetoxy, 6-hydroxy and 6-chloro derivatives of 4, 5-didehydro-L-ascorbic acid were obtained by reaction of ditosylated compound with nucleophilic reagents. The analysis of 3JH4H5 homonuclear coupling constants shows that all L-ascorbic acid derivatives except for epoxy and 4, 5-didehydro compounds exist in high population as gauche conformers across C-4--C-5 bonds, while 3JC3H5 heteronuclear coupling constants in 4, 5-didehydro derivatives indicate cis geometry along C-4--C-5 double bond. The X-ray crystal structure analysis of 2, 3-di-O-benzyl-5, 6-epoxy- and 5, 6-isopropylidene-L-ascorbic acid shows that the oxygen atoms attached at positions 2 and 3 of the lactone ring are disposed in a synperiplanar fashion. Besides that, the dioxolane ring adopts half-chair conformation. The molecules of epoxy derivative are joined into infinite chains by one weak hydrogen bond of C-H• • • O type. Two O-H• • • O and C-H• • • O hydrogen bonds link the molecules of 5, 6-isopropylidene compound into two-dimensional network. 6-Chloro derivative of 2, 3-di-O-benzyl-L-ascorbic acid showed the best cytostatic effects against all tested malignant tumor cells (IC50: ~18 uM).

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
0098092
0125003

Ustanove
Institut "Ruđer Bošković", Zagreb,
Tekstilno-tehnološki fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb,
Fakultet kemijskog inženjerstva i tehnologije, Zagreb

Časopis indeksira:


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


Uključenost u ostale bibliografske baze podataka:


  • CA Search (Chemical Abstracts)


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