-
Synthesis, structural studies, and cytostatic evaluation of 5,6-di-O-modified L-ascorbic acid derivativesGazivoda, Tatjana ...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 3JH-4-H-5 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 3JC-3-H-5 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-HO type. Two O-HO, and C-HO hydrogen bonds link the molecules of 5,6-di-O-isopropylidene compound into two-dimensional network. 6-Chloro derivative of 2,3-di-O-benzyl-l-ascorbic acid showed the best cytostatic effects against alltested malignant tumor cells (IC50Č 18 M).Vir: Carbohydrate research. - ISSN 0008-6215 (Vol. 341, no. 4, 2006, str. 433-442)Vrsta gradiva - članek, sestavni delLeto - 2006Jezik - angleškiCOBISS.SI-ID - 3438874
Avtor
Gazivoda, Tatjana |
Wittine, Karlo |
Lovrić, Iva |
Makuc, Damjan, 1978- |
Plavec, Janez |
Cetina, Mario |
Mrvoš-Sermek, Draginja |
Šuman, Lidija |
Kralj, Marijeta |
Pavelić, Krešimir, 1952- |
Mintas, Mladen |
Raić-Malić, Silvana
Teme
organic chemistry |
structural analysis |
L-ascorbic acid |
configurational analysis |
single crystal X-ray diffraction |
cytostatic activity
Vnos na polico
Trajna povezava
- URL:
Faktor vpliva
Dostop do baze podatkov JCR je dovoljen samo uporabnikom iz Slovenije. Vaš trenutni IP-naslov ni na seznamu dovoljenih za dostop, zato je potrebna avtentikacija z ustreznim računom AAI.
Leto | Faktor vpliva | Izdaja | Kategorija | Razvrstitev | ||||
---|---|---|---|---|---|---|---|---|
JCR | SNIP | JCR | SNIP | JCR | SNIP | JCR | SNIP |
Baze podatkov, v katerih je revija indeksirana
Ime baze podatkov | Področje | Leto |
---|
Povezave do osebnih bibliografij avtorjev | Povezave do podatkov o raziskovalcih v sistemu SICRIS |
---|---|
Gazivoda, Tatjana | |
Wittine, Karlo | |
Lovrić, Iva | |
Makuc, Damjan, 1978- | 24975 |
Plavec, Janez | 10082 |
Cetina, Mario | |
Mrvoš-Sermek, Draginja | |
Šuman, Lidija | |
Kralj, Marijeta | |
Pavelić, Krešimir, 1952- | |
Mintas, Mladen | |
Raić-Malić, Silvana |
Izberite prevzemno mesto:
Prevzem gradiva po pošti
Obvestilo
Gesla v Splošnem geslovniku COBISS
Izbira mesta prevzema
Mesto prevzema | Status gradiva | Rezervacija |
---|
Prosimo, počakajte trenutek.