Naslov
Enzymic Hydrolyses of Fully Acylated Derivatives of Beta-D-Ribose and Adenosine

Autori
Car, Željka ; Petrović Peroković, Vesna ; Matanović, Maja ; Tomić, Srđanka

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

Izvornik
2nd Central European Chemical Meeting : Book of Abstract / Vančik, Hrvoj - Varaždin : Vančik, Hrvoj, 2003, 11-11

Skup
2nd Central European Chemical Meeting

Mjesto i datum
Varaždin, Hrvatska, 19.06.2003. - 21.06.2003

Vrsta sudjelovanja
Poster

Vrsta recenzije
Nije recenziran

Ključne riječi
beta-D-riboza ; adenozin ; enzimi
(betha-D-ribose ; adenosine ; enzymes)

Sažetak
In recent years enzymes have been used as catalysts in regio-, stereo-, and chemoselective transformations of multifunctional organic compounds.1, 2 Enzymes are specially interesting in transformations of sugars that posess a number of hydroxyl groups of very similar reactivity.1 For that reason introduction and/or removal of protecting groups represent some of the most challenging transformations. In this work we report of enzymic hydrolyses of fully acylated derivatives of β -D-ribose and adenosine catalysed by a number of comercially available enzymes: pig liver esterase (PLE), porcine pancreas lipase (PPL), α -chymotrypsin, subtilisin, and butyrilcholine esterase (BChE). The best results in enzymic hydrolyses of 1, 2, 3, 4-tetra-O- acetyl-β -D-ribopyranose (1) and 1, 2, 3, 5-tetra- O-acetyl-β -D-ribofuranose (2) were achieved with PPL, PLE and BChE. 2, 3, 4-Tri-O-acetate was isolated as the main product when 1 was used as a substrate. Tetra-O-acetate 2 underwent enzymic hydrolysis followed by acetyl migration and the mixture of 1, 3, 5-tri-O-acetate and 1, 2, 5-tri- O-acetate was isolated. Hydrolysis of 9-β -D-(2, 3, 5-tri-O-acetyl ribofuranosyl)-6- acetylaminopurine (3) and 9-β -D-(2, 3, 5-tri-O- acetyl ribofuranosyl)aminopurine (4) with BChE as a catalyst led to deprotection of a primary 5-OH group. 1 W. J. Hennen, H. M. Sweers, Yi-F. Wang, Chi-H. Wong, J. Org. Chem. 53 (1988) 4939-4945 2 H. K. Singh, G. L. Cote, R. S. Sikorski, Tetrahedron Letters 34 (1993) 5201-5204

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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