Naslov
Synthesis and Spectroscopic Evidence of Aminoacid Esters of 4', 5'-Isobutiliden-O-protected Pyridine

Autori
Jadrijević-Mladar Takač, Milena ; Vuković, Jadranka ; Vikić-Topić, Dražen

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

Izvornik
Fourth European Congress of Pharmaceutical Sciences, in European Journal of Pharmaceutical Sciences Volume 6, Supplement 1 / Linden, H. Hans - Oxford : Elsevier, 1998, S29-S29

Skup
Fourth European Congress of Pharmaceutical Sciences

Mjesto i datum
Milano, Italija, 11.09.1998. - 13.09.1998

Vrsta sudjelovanja
Poster

Vrsta recenzije
Međunarodna recenzija

Ključne riječi
Pyridoxine ; 4' ; 5'-O-isobutiliden pyridoxine ; Esterification ; FT-IR spectroscopy ; 1D and 2 D 1H and 13C NMR spectroscopy

Sažetak
The preparation of alpha-aminoacid esters with pyridoxine (B6 Vitamin) were investigated. The scope of investigation was the synthesis of the potential 'prodrug' substances for the therapy of metabolic disorders that required an increased input of the corresponding essential alpha-aminoacids (i.e., cirrhosis, hepatic encephalopathy, liver and renal failure). For this purpose both, alpha-amino acid esters from BOC- and Z-N-protected aminoacids (Gly-OH, Ala-OH, Leu-OH and Phe-OH) and 4'5'-isobutylidene-pyridoxine with addition of DCC were synthesised. Chemical structures of synthesized esters were determined by IR, one- and two-dimensional, homo- and hetero-nuclear, 1H and 13C NMR correlation spectra (COSY, NOESY, HETCOR and HMBC). BOC-protected aminoacids gave better yields in comparing with Z-aminoacids, and the most reactive was BOC-Phe-OH. The use of unprotected pyridoxine , as an alcoholic component, in the same reaction conditions with an excess of aminoacid and DCC (Pyridoxine:aminoacid:DCC = 1:3:3) gave a mixture of mono-, di- and tri-esters. The removing of protected group by trifluoroacetic acid from aminoacid's part of the ester , gave an other product of reaction, so the selective removing of protecting group remains for the further investigation.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Farmacija

POVEZANOST RADA