Abstract
The synthesis of n-butanol and cinnamic alcohol esters of glucuronic acid and the esterification of ascorbic acid (vitamin C) with phenylbutyric acid was performed with lipase from Candida antarctica B (CAL-B, SP435) in a mainly solid-phase system. Products were obtained in 15 to 22 % yield. Computer modelling based on the structure of CAL-B was used to elucidate the access of glucuronic acid to the catalytic site of the lipase. A fixation of glucuronic acid via H-bonds to Q157, D134 and H224 during the transition state was observed. © Rapid Science Ltd. 1998
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Abdallah, OM, Kamel, MS and Mohamed, M.H. (1994). Phytochemistry 37:1689–1692
Adelhorst, K, Björkling, F, Godtfredsen, SE and Kirk, O (1990). Synthesis, 112–115
Ata, N, Oku, T, Hattori, M, Fujii, H, Nakajima, M and Saiki, I (1996). Oncol Res 8:503–511
Berger, S, Otten, MG and Steinbach, K (1992). Liebigs Ann Chem, 1045–1048
Bernstein, FC, Koetzle, TF, Williams, GJ, Meyer, EE, Brice, MD, Rodgers, JR, Kennard, O, Shimanouchi, T and Tasumi, M (1977). J Mol Biol 112:535–542
Cao, L, Fischer, A, Bornscheuer, UT and Schmid, RD (1997). Biocatal Biotransform 14:269–283
De Bont, DB, Leenders, RG, Haisma, HJ, Van der Meulen-Muileman I and Scheeren, HW (1997). Bioorg Med Chem 5:405–414
Ducret, A, Giroux, A, Trani, M and Lortie, R (1996). Biotechnol Bioeng 48:214–221.
Fiechter, A (1992). Trends Biotechnol 10:208–217
Goodford, PJ (1985). J Med Chem 28:849–857
Humeau, C, Girardin, M, Coulon, D and Miclo A (1995). Biotechnol Lett 17:1091–1094
Kimura, Y, Okuda, H, Nishibe, S and Arichi, S (1987). Planta Med 53:148–153
Nicoletti, M, Galeffi, C, Messana, I, Marini-Bettolo, GB, Garbarino, JA and Gambaro, V (1988). Phytochemistry 22:639–641
Nihro, Y, Sogawa, S, Izumi, A, Sasamori, A and Sudo, T (1992). J Med Chem 35:1618–1623
Nilsson, KG (1987). Carbohydr Res 167:95–103
Otto, RT, Bornscheuer, UT, Syldatk, C and Schmid, RD (1998a). Biotechnol Lett 20:437–440
Otto, RT, Bornscheuer, UT, Syldatk, C and Schmid, RD (1998b). J Biotechnol 64:231–237
Pleiss, J, Fischer, M, Schmid, RD (1998). Chem Phys Lipids, in press
Slagowska, A, Zgorniak-Nowosielska, I and Grzybek, J (1987). Pol J Pharmacol Pharm 39:55–61
Uppenberg, J, Ohrner, N, Norin, M, Hult, K, Kluywegt, GJ, Patkar, S, Waagen, V, Anthonsen, T and Jones, TA (1995).Biochemistry 34:16838–16851
Ushiyama, M, Kumagai, S and Furuya, T (1989). Phytochemistry 28:3335–3339
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Otto, R.T., Bornscheuer, U.T., Scheib, H. et al. Lipase-catalyzed esterification of unusual substrates: Synthesis of glucuronic acid and ascorbic acid (vitamin C) esters. Biotechnology Letters 20, 1091–1094 (1998). https://doi.org/10.1023/A:1005478131779
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DOI: https://doi.org/10.1023/A:1005478131779